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Vacation Rentals in Key West, FL

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$175
Per Night
1 / 21
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1 Bedroom, 4 Bathrooms, Sleeps 2
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$209
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1 / 15
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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$408
Per Night
1 / 33
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$118
Per Night
1 / 20
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Studio, 1 Bathroom, Sleeps 2
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • 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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$239
Per Night
1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
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 family or group of friends. Experience endless sunshine and the incomparable charm... 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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From
$5,250
Per Month
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this... View all property information
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$219
Per Night
1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • 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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$250
Per Night
1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
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About this property
Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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5 of 5 stars Reviewed December 31, 2013
Really enjoyed staying at Shelleys Rooftop. Far enough down Duval St. to be away from the crowds but just a walk away to the crowds and popular bars. Spent Christmas with...
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From
$218
Per Night
1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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From
$233
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Balcony
  • Dishwasher
  • Garden or Yard
  • Hot Tub
  • Internet Access
  • Private Beach
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
This is not just a rental but OUR Vacation Home as well. We are the ONLY 1 bedroom condo in the entire complex, 4th floor Penthouse. Included in your rental is the use of 2 adult bikes, secure wireless internet, local and long distance telephone continental USA and Canada, the use of the pool,... View all property information
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5 of 5 stars Reviewed October 17, 2014
My husband and I chose Key West to celebrate our 25th anniversary. Can't say enough about this gorgeous condo. In addition to the cleanliness, ease of reservation, security and...
5 of 5 stars Reviewed July 12, 2014
Checking in was a fast no hassle process. Condo was clean and decorations were wonderful with all the comforts if home . Although we did not use the bikes they are a nice touch...
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From
$225
Per Night
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
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  • Wheelchair access
  • Elder access
About this property
Make memories the whole family will cherish in this great family friendly condo in Key West. It's close to all the major attractions on the island but far enough away that everyone can get a good night's sleep if they want. Want to go to the beach? The condo is a short drive to Smathers Beach.... View all property information
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2 of 5 stars Reviewed April 15, 2014
We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
5 of 5 stars Reviewed February 10, 2014
I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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From
$268
Per Night
1 / 33
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (22) Make Inquiry
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, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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5 of 5 stars Reviewed November 16, 2014
Stayed in this condo for 3 nights during Key West boat races. Check in with Key west Vacation rentals was easy, they're right on premises. Condo is above Duval Square. Very...
4 of 5 stars Reviewed October 27, 2014
This was a very nice, two-bedroom rental very near Duval and Truman in Key West. The property is well-kept, and the two-seater hot tub was nice. Our only problems were when...
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From
$199
Per Night
1 / 14
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2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (12) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
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5 of 5 stars Reviewed November 18, 2014
We were in key west playing music at a friend's wedding around the corner at old town manor. The Bahama House is perfect! it is close to everything, there's a beautiful pool...
5 of 5 stars Reviewed August 21, 2014
What an amazing location! Just half a block from Faustos market and one block from the Trolley stop. Could not have planned that any better. One of our group members had walking...
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From
$225
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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3 of 5 stars Reviewed November 16, 2014
This is a nice 2 bed 2 bath condo, clean, comfortable, and nicely decorated. The pool and hot tub in this small resort were very nice. Kitchen was adequate with new pans - I...
5 of 5 stars Reviewed May 6, 2014
The location was great. Very Quiet. Exactly as described. Would definitely stay here again! I was also incredibly grateful the for the quick response times to my emails.
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From
$700
Per Night
1 / 25
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
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About this property
NEWLY LISTED WITH PLENTY OF AVAILABILITY Key West Vacation Rental "SECRET VILLA II" A Hidden Jewel in Historic Old Town Key West Our property "SECRET VILLA" is so popular and in such high demand, the owner has purchased and remodeled the mirror image of it to create "SECRET VILLA II" Location,... View all property information
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From
$250
Per Night
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
About this property
The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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5 of 5 stars Reviewed March 22, 2014
A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
5 of 5 stars Reviewed January 23, 2014
The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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From
$348
Per Night
1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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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
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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From
$208
Per Night
1 / 26
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Studio, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
Brand New to the Rental Market! This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go upstairs to a large shared deck, perfect... View all property information
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5 of 5 stars Reviewed November 11, 2014
This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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From
$138
Per Night
1 / 29
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Studio, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) 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 Southernmost Sanctuary Suites The Heron Suite is located street side with it's own porch for people watching. Get one of Ana's Cuban mixes - it just doesn't get any better! Conveniently located to the beach, Duval Street, great restaurants, Ana's for great Cuban fare and morning coffee -... View all property information
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4 of 5 stars Reviewed July 28, 2014
Located right by the Southernmost Hotel and a block off Duval this was a great stepping off point for fun in Key West. Cuban market on the corner for café con leche each morning...
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1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
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5 of 5 stars Reviewed November 3, 2013
I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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From
$138
Per Night
1 / 24
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) 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 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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From
$198
Per Night
1 / 23
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Studio, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • 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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From
$178
Per Night
1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • 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
$408
Per Night
1 / 30
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3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (23) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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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From
$975
Per Week
1 / 24
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Ocean Views
  • Pool Table
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
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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From
$257
Per Night
1 / 26
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (19) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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5 of 5 stars Reviewed July 31, 2014
Great rental, right in the middle of everything. We arrived and everything was as described. Wifi was a great bonus for teenage son. House clean and tidy with plenty of linen...
4 of 5 stars Reviewed June 14, 2014
Everything about our vacation at Casa del Sol was perfect. The apartment is a perfect size and the rooms were decorated to match the Key West atmosphere, which we loved! The...
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From
$290
Per Night
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (13) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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 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...
5 of 5 stars Reviewed June 23, 2014
We had a wonderful stay at the Atlantic Sunrise condo. The condo was tastefully decorated and well appointed. It was roomy and very comfortable for the four of us. The fine...
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From
$138
Per Night
1 / 25
Payment Protection
Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) 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 Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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5 of 5 stars Reviewed October 29, 2014
We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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From
$258
Per Night
1 / 36
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
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
$175
Per Night
1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
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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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.
4 of 5 stars Reviewed May 23, 2014
Condo was a great location. Near beaches and activities. Great place to relax. Owner was very courtious. Pool was a little small but the facilities were beautiful.
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From
$148
Per Night
1 / 21
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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 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
$258
Per Night
1 / 31
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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
  • ?
About this property
One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
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4 of 5 stars Reviewed July 21, 2014
Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
5 of 5 stars Reviewed March 24, 2014
Excellent accommodations! Slept five adults comfortably, but the one bathroom was a little rough at times. We're all friends so no big deal! Especially enjoyed the hot tub and...
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From
$138
Per Night
1 / 26
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Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Mallory 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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5 of 5 stars Reviewed June 23, 2014
Wonderful. And 'Ive stayed here several times. We also bring our 2 yorkies I love the Mallory, the Truman. So close to everything. Room is beautiful too. And very reasonable in...
5 of 5 stars Reviewed June 18, 2014
Very clean, great location, kitchen well equipped, dog friendly, bed was comfortable, quiet location, shower a little small
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From
$1,300
Per Week
1 / 31
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2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (5) 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
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million... View all property information
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4 of 5 stars Reviewed November 24, 2012
Arrived with spouse and our 2 adult children. This condo was clean, had all the amenities that we could have hoped for. Nice quiet neighborhood, yet close to Duval St. Everything...
5 of 5 stars Reviewed February 6, 2011
Close to Duval St, and Mallory Square - within a 10 min walk with small kids. Amenities were great - kitchen, washer/dryer, family room. Access to pool. Looking forward to a...
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From
$167
Per Night
1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
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  • Wheelchair access
  • Elder access
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About this property
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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From
$198
Per Night
1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Details Reviews (32) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This is a non-smoking condo (smoking on the balcony only) with that "home away from home" appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
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5 of 5 stars Reviewed November 16, 2014
Wow, did we EVER choose the right place to stay. We went to Key West for the week for my oldest daughter to have a Destination wedding their. It was our first time going to Key...
5 of 5 stars Reviewed November 10, 2014
This is a great option for the Keys. Close to all the major attractions of the keys. Very comfortable and clean. Pam has done an amazing job and is sweetheart to talk too. We're...
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From
$178
Per Night
1 / 26
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (47) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have been saved... View all property information
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3 of 5 stars Reviewed November 11, 2014
The Osprey Nest accommodation is very comfortable and pleasant. It's a bit of a hike from the action on Duval Street, which is good because it's in a quiet neighborhood, but a...
5 of 5 stars Reviewed August 20, 2014
We stayed here for a week in August '14. Our friends stayed at the Southernmost Hotel and spent almost $1000 more than us for a double queen room. The place is very nice. Clean...
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From
$178
Per Night
1 / 22
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (28) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration... View all property information
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5 of 5 stars Reviewed September 2, 2014
I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
5 of 5 stars Reviewed May 1, 2014
My husband and I spent 10 nights at Heron Hideaway in celebration of our 20th anniversary. Every thing that we needed was provided in this very clean and ideally located home...
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From
$268
Per Night
1 / 25
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2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
Details Reviews (14) Make Inquiry
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
This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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5 of 5 stars Reviewed August 21, 2014
I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
5 of 5 stars Reviewed August 18, 2014
Positioned right with ammeneties, beaches, and bars close by. Short stroll to any need. Place was very clean and with 2 bedrooms, 2.5 baths , pull out beds was very...
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From
$400
Per Night
1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Outdoor...
  • 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
This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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5 of 5 stars Reviewed June 7, 2011
This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
5 of 5 stars Reviewed March 5, 2010
The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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From
$138
Per Night
1 / 27
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Studio, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Hot Tub
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 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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From
$208
Per Night
1 / 25
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2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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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From
$178
Per Night
1 / 27
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (22) 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
  • ?
  • ?
About this property
The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
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4 of 5 stars Reviewed April 24, 2014
The suite was very clean and well taken care of. The pool was terrific. There is a nice fairly private deck to sit under some magnificent trees. We rented bicycles which made it...
4 of 5 stars Reviewed April 6, 2014
The location a few blocks off Duval and not right on Olivia street was great. By not right on Olivia street I mean you walk through a tiny parking lot, past the pool, down a short...
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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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From
$289
Per Night
1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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From
$378
Per Night
1 / 34
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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5 of 5 stars Reviewed July 25, 2014
This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
5 of 5 stars Reviewed June 6, 2014
Very clean, looks recently redone. Great set up, plenty of room for the six of us. Most comfortable bed ever. Literally steps from Duval St. I would definitely stay here again.
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From
$188
Per Night
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
  • ?
  • Wheelchair access
  • Elder access
  • x
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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$188
Per Night
1 / 31
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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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From
$338
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1 / 32
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in Duval Square (between Duval St and Simonton St) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), This development extends from Duval Street to Simonton Street and is in the heart of historic Old Town. It is comprised of residential... View all property information
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5 of 5 stars Reviewed June 1, 2014
Namely, Case Key West, where we stayed with a group of 6. The staff was more than helpful, especially Rick Haskins. My Husband uses a wheelchair and he was so helpful and we were...
4 of 5 stars Reviewed April 2, 2013
Had a great two-night stay with my all-adult family of 5. The condo has three full bedrooms so it was very comfortable for our group. The condo also features 2 completely windowed...
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$450
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1 / 9
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
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5 of 5 stars Reviewed August 16, 2014
I came down with my family and we loved this place. We had a direct view of the water and it was amazing waking up every morning to see that. Very relaxing. Friendly people...
5 of 5 stars Reviewed May 29, 2014
This was our first trip to Key West and everything was great including the condo. Very nice view, great pool, short walk to very nice beach. What more would you want.
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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.