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Vacation Rentals in Key West, FL

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$208
Per Night
1 / 26
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Studio, 1 Bathroom, Sleeps 2
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$199
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1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$250
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1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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$219
Per Night
1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
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5 of 5 stars Reviewed September 25, 2014
Our place was beautiful. Beds were comfortable, beautifully appointed and more room than we ever imagined! Close to everything! Very clean and all the amenities you need. Check in...
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$198
Per Night
1 / 23
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Studio, 1 Bathroom, Sleeps 4
Booking
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of Southern Palms Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment... View all property information
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5 of 5 stars Reviewed August 12, 2014
We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait to...
5 of 5 stars Reviewed July 29, 2014
From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport pick-ups...
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$310
Per Night
1 / 21
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
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5 of 5 stars Reviewed December 17, 2014
This is a great place to stay that puts you in the heart of Key West and has off-street parking! The unit has been completely remodeled including a full kitchen but still...
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$239
Per Night
1 / 14
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
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5 of 5 stars Reviewed August 18, 2014
This place was everything we could've hoped and MORE! The house was beautiful and had such am authentic key west charm. The historic nature of the building really made it warm and...
2 of 5 stars Reviewed July 15, 2014
We had a family of five stay in the Grand Bahama Suite July 6-9. Three days before our vacation we received an email that there would be construction going on and there was a...
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$357
Per Night
1 / 27
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2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4... View all property information
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5 of 5 stars Reviewed June 30, 2013
The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
5 of 5 stars Reviewed May 25, 2013
An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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$248
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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From
$195
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (39) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
  • x
About this property
This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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4 of 5 stars Reviewed November 12, 2014
We found this condo to be well-stocked and have everything that we needed, like a home-away-from-home. Communication with the owners was professional and prompt. They really...
5 of 5 stars Reviewed August 17, 2014
For all going to Key west and need lodging. Tropical Escape is the place. It has the most perfect location in order to plan your trip around the island. It is also very safe and...
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From
$118
Per Night
1 / 20
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Studio, 1 Bathroom, Sleeps 2
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of TROPICAL VILLAGE Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning... View all property information
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5 of 5 stars Reviewed September 17, 2014
This unit was perfect for our needs. It's just a small studio cottage, but has a nice porch and access to the large "shared" (and I put it in quotations because we had the pool...
4 of 5 stars Reviewed July 28, 2014
This rental was almost exactly how I imagined it to be when I booked it. It was small, yet quiet with an adjacent pool that was large enough for my float and warm enough for me...
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From
$178
Per Night
1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The... View all property information
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5 of 5 stars Reviewed November 14, 2014
I booked our condo through VRBO based on location and price. What a great find. Perfect location to Old Town activity and only a mi,e leasurely walk to Mallory Square and the...
4 of 5 stars Reviewed October 8, 2014
Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter! Very...
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From
$198
Per Night
1 / 24
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Studio, 1 Bathroom, Sleeps 2
Details Reviews (19) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft... View all property information
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5 of 5 stars Reviewed September 2, 2014
Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
5 of 5 stars Reviewed March 12, 2014
We absolutely loved Harrison's Hideaway. It was in the perfect location - 1/2 block off of Duval, a very short bike ride to the beach. It was immaculate, too - must have been...
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$138
Per Night
1 / 35
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Studio, 1 Bathroom, Sleeps 4
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Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
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5 of 5 stars Reviewed October 17, 2014
We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
4 of 5 stars Reviewed September 24, 2014
It was a great location out of the way but by everything. Also the room was very secluded to the back of the property for a nice romantic time.
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From
$167
Per Night
1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room,... View all property information
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From
$348
Per Night
1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
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About this property
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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5 of 5 stars Reviewed October 13, 2014
The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
5 of 5 stars Reviewed July 25, 2014
I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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$408
Per Night
1 / 33
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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5 of 5 stars Reviewed July 29, 2014
This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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From
$158
Per Night
1 / 24
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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5 of 5 stars Reviewed July 16, 2014
Excellent location just off Duval street but still very quiet and private feeling. The unit was small but had all the amenities we needed. The private hot tub and the pool and...
5 of 5 stars Reviewed May 29, 2014
I had stayed at Little Havana Suite numerous years ago and loved it. I knew I wanted to stay in the property again... I ended up traveling solo as my other half got stuck working...
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From
$298
Per Night
1 / 29
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2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (21) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of 4 exclusive units at Abbey Road, The original Cuban tile has been preserved throughout the house, wherever possible. Upon entering the spacious living room, a large tropical sectional queen sleeper sofa allows you to comfortably watch the 46” flat screen TV/DVD. Also available is an I-Pod... View all property information
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5 of 5 stars Reviewed December 7, 2014
My spouse brought me to KW to celebrate my birthday, what a truly wonderful time we experienced on our entire trip. Lennon Lodge was absolutely cozy, comfortable, and private...
5 of 5 stars Reviewed October 30, 2014
We stayed in Lennon's Lodge for 7 days, and wish we could have stayed forever. The property itself is clean, quiet and private and the Lodge itself is beautiful, well-kept and...
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From
$214
Per Night
1 / 13
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (41) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony on the 2nd floor deck. In case you would like to work on vacation the unit has a wireless DSL connection. There is one assigned parking space per unit.... View all property information
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3 of 5 stars Reviewed May 21, 2014
In last year's review, I said I would unhesitatingly stay here again. I did. And was far less charmed. I do love the Truman Annex location and the design of the condo. The...
5 of 5 stars Reviewed June 18, 2013
very nice place in excellent location
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From
$318
Per Night
1 / 28
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (7) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
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4 of 5 stars Reviewed September 29, 2014
Only issues was the ants running around the kitchen counters. Parking is only for one car. Location was a plus, Jacuzzi was nice to wind down at nite.
5 of 5 stars Reviewed April 24, 2014
The amelia House was perfect! House was so comfortable. Very clean and well taken care of. The rooms were spacious and roomy. Beds were so comfortable and big. Loved the...
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From
$178
Per Night
1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Reviews (20) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!... View all property information
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5 of 5 stars Reviewed June 26, 2014
Our stay at the Abaco Suite through Key West Vacation Rentals was near perfect. The rental company was very professional and helpful. The check-in and out was seamless. We...
4 of 5 stars Reviewed April 7, 2014
TThis is a lovely 1-bedroom townhome situated in an ideal location among 8-9 units on around a truly beautiful courtyard. First off, you really get the bang from your buck at this...
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$288
Per Night
1 / 34
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
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5 of 5 stars Reviewed December 13, 2014
We loved everything about this cottage and gated property! AND we are making plans to come down again next year with another group of KW virgins!
5 of 5 stars Reviewed December 2, 2014
Great 2 bedroom with comfortable king beds, full kitchen, living room, dining room, pool, everything you need to have a relaxing vacation in key west. 1 Block to Duval, few...
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From
$178
Per Night
1 / 19
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Studio, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value. This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,... View all property information
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5 of 5 stars Reviewed November 27, 2014
Papa's Hideaway is a hidden paradise! It is beautiful and comfortable and close to everything. The bed was extremely comfortable and furnished with everything we needed for a...
4 of 5 stars Reviewed March 18, 2014
Loved the location to everything,walking distance and even had parking included in the cost of rental...made me feel relaxed instantly,loved hanging out at the pool and meeting...
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From
$175
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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5 of 5 stars Reviewed December 11, 2014
This condo at Sunrise at Seaside is perfect for a family vacation. We stayed there last Thanksgiving weekend and had a wonderful time. The condo is very well maintained and...
4 of 5 stars Reviewed June 9, 2014
Very good price for a 2 bed 2 bath in Key West! It Was clean and just what we needed! It was also not right in downtown close to everything so we could get away hen we wanted.
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From
$290
Per Night
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (14) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Wake up to the sun rising over the sparkling Atlantic Ocean. Watch heron fish for breakfast in the flats below as you drink your coffee. Stretch out on the balcony while flocks of pelicans soar above you and the rocks disappear and reappear with the tide below you. Sip a cocktail and watch the... View all property information
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5 of 5 stars Reviewed December 7, 2014
All the previous reviews are completely accurate. The location is quiet and peaceful but only minutes away (by car) from Duval Street. Inside, the condo is very well-appointed...
5 of 5 stars Reviewed November 2, 2014
This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
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From
$258
Per Night
1 / 22
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Welcome to Artist House: a 2 bedroom 2.5 bath rooftop townhome located within the gated community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located so that you can park your car in the... View all property information
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5 of 5 stars Reviewed November 10, 2014
My husband and I have rented this unit twice now and it is the perfect place. The rental company is wonderful to work with try to get you in to the unit early if possible. This...
4 of 5 stars Reviewed August 5, 2014
Nice condo right on duval st. Good location for a more quiet stay.Cvs right around the corner Rooms where nice. Hot tub on patio is a plus. Only negative comment is I wish we...
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From
$138
Per Night
1 / 24
Payment Protection
Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly the Osprey Suite) - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen... View all property information
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5 of 5 stars Reviewed August 28, 2014
This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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$138
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1 / 25
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Studio, 1 Bathroom, Sleeps 4
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book before... View all property information
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5 of 5 stars Reviewed August 5, 2014
The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or a...
4 of 5 stars Reviewed July 25, 2014
The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we were...
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$1,725
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Ocean Views
  • Pool Table
  • Private Outdoor...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
NOVEMBER SPECIAL!! Stay 28 days between Nov 2nd and Dec 6, 2014 for only $3900. MINIMUM STAY FOR THIS PROPERTY IS 28 DAYS. Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage,... View all property information
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$208
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2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Suitable for children
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About this property
Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
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5 of 5 stars Reviewed October 13, 2014
The location of our rental was fabulous. We were in walking distance of everything Key West had to offer. Having the front porch open would have made the stay even better.
4 of 5 stars Reviewed September 29, 2014
Great place to stay! Located right on Duval Street. Two rooms with double beds and a pull out bed-couch. A/C nice and cold when you need to get out of the summer heat in the...
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$138
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1 / 22
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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
The Truman Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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3 of 5 stars Reviewed October 29, 2014
Late reservation so I couldn't be picky. Bed mattress needs to be replaced. Nighttime security light didn't work. Pool nice. Clean full kitchen
5 of 5 stars Reviewed June 6, 2014
The home was clean and quiet. It was just perfect for the two of us. We would recommend it to others.
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$158
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of the Nightly group unit Tres Flores You won't find a better location...and private off-street parking is just outside your door. Turn down 'Free School House Lane' (the entrance to Nancy's Secret Garden and 1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen... View all property information
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5 of 5 stars Reviewed November 10, 2014
good place. Location is great, apartment is in very good condition. Two balconies. For two it is a great choice. Very cosy and clean, quite big. Free parking. I can recommend...
5 of 5 stars Reviewed August 19, 2014
Definitely an ideal location for all things Key West. Never had to walk very far to get to most every place we wanted to go. The place was clean and always comfortable...
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From
$248
Per Night
1 / 29
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby bars,... View all property information
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5 of 5 stars Reviewed July 4, 2009
My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
5 of 5 stars Reviewed July 2, 2009
Great location off the upper section of Duval. Close enough to walk to everything but far enough to be quiet. Perfect size for 2 or 4 people. Clean and comfortable. Would...
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Grill
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
Look no further you have found a beautiful 2 bedroom 2 bath 'Shot-Gun' house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size... View all property information
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From
$338
Per Night
1 / 29
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
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5 of 5 stars Reviewed December 9, 2014
Our 6th year renting "Hemingway's View" and we loved every minute we were there! Wonderful and relaxing rental that allows us to bring out two yorkies. We like that the property...
4 of 5 stars Reviewed June 30, 2014
Great house pretty much right off Duval. Very close to great restaurants, bars, and shops, and a very short walk to the beach. Plenty of room for three couples and one child. Not...
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$188
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1 / 27
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Located inside the Villas known as Old Town Garden Villas Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, cordless telephone, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, a/c... View all property information
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5 of 5 stars Reviewed June 25, 2014
I can't say enough about this rental! Excellent location, very clean and the courtyard is amazingly beautiful.. You feel like you are in a private paradise on the island.. The...
5 of 5 stars Reviewed June 14, 2014
We stayed here the first week of June 2014. We were welcomed by management at the rental office, offered a cold beverage, and given an umbrella for our use. We were picked up at...
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$158
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1 / 28
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Wheelchair access
  • Elder access
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About this property
Part of the Nightly group unit Tres Flores Additional amenities include: coffee maker, nearby bank, nearby internet cafe, no phone, off-site shared pool, nearby medical services, kitchenette, nearby grocery, close to duval, ironing board, cookware, nearby post office, nearby atm, golf course,... View all property information
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5 of 5 stars Reviewed October 13, 2014
This cute little upstairs apartment was a great place to fix a quick breakfast & have coffee on the covered balcony before heading off to explore historical Old Town. The place...
2 of 5 stars Reviewed May 26, 2014
Overall this unit is tired and poorly repaired (This building has several units ) Has window A/C units that are very loud and cool poorly , ( Helps cover the street noise ) If...
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$258
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1 / 36
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2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
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About this property
Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
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5 of 5 stars Reviewed July 1, 2014
Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
5 of 5 stars Reviewed February 4, 2014
We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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From
$150
Per Night
1 / 16
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
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  • Suitable for children
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About this property
Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 6 and offers a private patio, a spa pool with jacuzzi... View all property information
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$408
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
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5 of 5 stars Reviewed November 10, 2014
The Key Escape was everything we wanted and more for a relaxing week in Key West -- 5++ stars!!! It was comfortable, modern, and excellent service!
5 of 5 stars Reviewed October 9, 2014
Excellent property and staff! Great location, great beds!!! Very clean. Would definitely rent again!
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$188
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1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (37) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located inside the Villas known as Old Town Garden Villas Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly... View all property information
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5 of 5 stars Reviewed October 27, 2014
Just returned home from a 10 day stay and it was an awesome experience! Place was nice and clean. The daily room service was great, even if we didn't always use it. Even though we...
4 of 5 stars Reviewed August 12, 2014
Pros: This place is close enough to everything but quiet enough as well. The central garden/sitting area is very nice and has either sun or shade to fit your needs. The room set...
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$188
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a... View all property information
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5 of 5 stars Reviewed November 18, 2014
For the location, the price was a bargain. There were a couple of lights that needed to be replaced (no biggie). Andros suite was more of a condo. Full kitchen, and all the...
5 of 5 stars Reviewed November 12, 2014
We loved our stay at the Andros Suite. This is one of a gated cluster of duplex houses on the quieter side of Key West. The apartment was so nicely decorated and had everything...
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$188
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
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5 of 5 stars Reviewed December 8, 2014
The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
4 of 5 stars Reviewed November 20, 2014
We booked here for one night because of the location. This worked out well for 2 couples - one private bedroom with full bath and separate entrance, one pull-out sofa bed with a...
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From
$275
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1 / 5
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
About this property
Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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3 of 5 stars Reviewed September 3, 2013
Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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$268
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room, dining... View all property information
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5 of 5 stars Reviewed November 2, 2013
Very attractive, well located, and with so many nice little extras. The managers are attentive and very helpful. It's easy to tell that a lot of thought and care go into keeping...
5 of 5 stars Reviewed July 2, 2009
My favorite part of this cute conveniently located condo was the jacuzzi. The first thing we did was relax in the spa before a long night on Duval street. This condo was very...
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$268
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Inside, you will find all of the comforts of home and more..... This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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5 of 5 stars Reviewed December 15, 2014
We stayed at the family house for our 10 year anniversary. After looking at numerous rental properties, we elected to go through Key West Vacation Rentals. After picking the...
5 of 5 stars Reviewed December 10, 2014
This a beautiful space very near all the action on Duval Street. It was a 10 minute walk to the beach where we rented chairs and an umbrella. 2 Comfy beds and a sofa bed ---not so...
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From
$198
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1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes... View all property information
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5 of 5 stars Reviewed October 8, 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed August 19, 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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$268
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
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4 of 5 stars Reviewed November 11, 2014
Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
4 of 5 stars Reviewed July 2, 2014
Condo was in a great location, the staff was very helpful and friendly. Had one maintenance problem which was the garbage disposal and was fixed with in 24 hours. There is no...
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$265
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
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5 of 5 stars Reviewed May 30, 2014
The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
3 of 5 stars Reviewed February 1, 2014
The unit waiting for us was not the unit promised in our reservation. The location was nice and very scenic. The center courtyard with large heated pool and large hot tub were...
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Key West Vacation Rentals

Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

Where to rent in Key West, Florida

Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Key West Bars and Restaurants

Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Sightseeing and Activities in Key West

Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.