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Vacation Rentals in Key West, FL

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$189
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1 / 13
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1 Bedroom, 1 Bathroom, Sleeps 4
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$175
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1 Bedroom, 4 Bathrooms, Sleeps 2
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$495
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3 Bedrooms, 4 Bathrooms, Sleeps 6
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$198
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1 / 23
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Studio, 1 Bathroom, Sleeps 4
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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 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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$208
Per Night
1 / 26
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Studio, 1 Bathroom, Sleeps 2
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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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$5,000
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1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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About this property
Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most... View all property information
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$250
Per Night
1 / 15
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • 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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$298
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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5 of 5 stars Reviewed October 28, 2014
Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
4 of 5 stars Reviewed September 11, 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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From
$975
Per Week
1 / 24
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Pool Table
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair 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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From
$138
Per Night
1 / 24
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Studio, 1 Bathroom, Sleeps 4
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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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$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
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  • Wheelchair 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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$348
Per Night
1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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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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$178
Per Night
1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • 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
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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$188
Per Night
1 / 24
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Studio, 1 Bathroom, Sleeps 4
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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. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
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5 of 5 stars Reviewed August 8, 2014
I stayed at Papa's hideaway for 11 nights. I spent some of the time with girlfriends and the last few days by myself. Torrents of spring was perfect for both parts of my trip...
4 of 5 stars Reviewed February 10, 2014
I stayed in unit number 1 for 7 nights and I didn't want to leave!! The property is safe and secure and is perfectly hidden but still a walk to all you need. There is a bbq on...
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$208
Per Night
1 / 29
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair 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
$318
Per Night
1 / 28
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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$250
Per Night
1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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$178
Per Night
1 / 28
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1 Bedroom, 1 Bathroom, 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 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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From
$138
Per Night
1 / 25
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Studio, 1 Bathroom, Sleeps 4
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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
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
$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
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  • 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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$248
Per Night
1 / 26
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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
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  • Wheelchair access
  • Elder access
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About this property
The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
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5 of 5 stars Reviewed June 5, 2014
Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
4 of 5 stars Reviewed April 16, 2014
The location was good. Not far from Duval. It was very clean. I really enjoyed the hot tub on the patio. The beds were so comfortable :)) Unfortunately a car was parked in front...
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From
$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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$408
Per Night
1 / 22
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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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 Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full... View all property information
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5 of 5 stars Reviewed July 1, 2014
We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable...
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$368
Per Night
1 / 34
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and... View all property information
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5 of 5 stars Reviewed March 10, 2013
2br 2 bath with sleeper sofa in main room. Pictures are accurate. Private pool and location make this an ideal stay for more than 3 nights. VERY close to the action on Duvall...
4 of 5 stars Reviewed October 8, 2011
DuPont House was a great place to stay in a great location. You are close enough to walk to everything but just far enough off on a side street so you don't hear any noise from...
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From
$1,142
Per Night
1 / 28
6 Bedrooms, 7 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
  • x
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About this property
Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
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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
$358
Per Night
1 / 25
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Grill
  • Heated Pool
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The beaches of the Atlantic Ocean are less than a 7 minute walk...4 blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder,... View all property information
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5 of 5 stars Reviewed October 25, 2014
The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
5 of 5 stars Reviewed August 5, 2014
This is a wonderful home in a great location - easy walking to almost everything. We loved the pool and the homes layout. Very clean and bright with TV's in both large bedrooms...
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From
$338
Per Night
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
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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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From
$225
Per Night
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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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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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
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  • Hot Tub
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  • Satellite TV
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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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  • Balcony
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  • Pool
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
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About this property
Part of the Nightly Group PALM GARDENS Flamingo Hideaway is a spacious unit. Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details. The original Dade County pine walls have been saved to create that unique... View all property information
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5 of 5 stars Reviewed July 31, 2014
The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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4 Bedrooms, 2 Bathrooms, Sleeps 12
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About this property
Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house. Your... View all property information
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5 of 5 stars Reviewed July 29, 2014
Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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$300
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Private Beach
  • Sauna
  • Shared Outdoor Pool...
  • Water Views
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About this property
BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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2 Bedrooms, 1 Bathroom, Sleeps 4
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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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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Air Conditioning
  • Grill
  • Hot Tub
  • 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
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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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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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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$248
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
UPDATE: New King-sized bed w/ pillow top mattress installed June 2015 Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you to the relaxing hot tub and then to... View all property information
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4 of 5 stars Reviewed November 16, 2014
The condo was a very nice rental on the south side of Key West. The decor was modern and the condo had a classy feel. The large balcony patio was wonderful to sit out on in the...
5 of 5 stars Reviewed June 7, 2014
This property was a beautiful way to do Key West. Private beach, big salt water pool and Jacuzzi and grills. The view was the best part of the condo! It was also very clean...
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$250
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Air Conditioning
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  • Dryer
  • Garden or Yard
  • Grill
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  • Private Outdoor...
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About this property
This delightful one-bedroom, one-bath conch cottage is set back from White Street, which runs the fourteen-block width of the island from the Gulf of Mexico to a fishing pier jutting out into the wide Atlantic Ocean. The street, named after Colonel Joseph White, memorializes a bit of Key West... View all property information
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5 of 5 stars Reviewed October 7, 2014
My wife and I have made several trios to Key West but we decided to stay in a house for this trip, and we couldn't have been happier to find this gem. The house was better than...
4 of 5 stars Reviewed August 6, 2014
This is a perfect cottage for two people. Located in a quiet part of Old Town but only 10 minutes walk from all the excitement of Duvall Street. Garden and swimming pool were...
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Heated Pool
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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5 of 5 stars Reviewed July 24, 2014
Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
5 of 5 stars Reviewed May 9, 2014
We rented the Tropical Retreat for our parents during our wedding in Key West. They were extremely happy with everything that this house had to offer. Some of the comments I heard...
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Dryer
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  • Safe
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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. Stroll out your door and enjoy cafe con leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork... View all property information
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5 of 5 stars Reviewed February 12, 2014
We stay at the Palm Isle on White Street every year, and love it! It's perfectly close to everything in Old Town Key West, as well as the beaches. You can walk most places, but...
4 of 5 stars Reviewed January 2, 2014
Plenty of space for 2 people. Clean and well maintained. Bed was a little soft for me. It is on White St. and while not a busy street by city standards, it is one of the main...
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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
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  • Hot Tub
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  • Pool
  • Satellite TV
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  • Smoking allowed
  • Suitable for children
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About this property
Romantic Retreat features a king pillow-top bed, Tommy Bahama furniture, flat screen TV and tropically inspired original fine art. The recently renovated kitchen includes granite counter tops, under counter refrigerator, microwave, toaster/oven, coffee maker, blender and soft mood lighting under... View all property information
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5 of 5 stars Reviewed May 16, 2014
Heaven in the middle of Key West. Beautifully decorated, clean, perfect pool & hot tub, Amazing! Staff is very attentive and replenishes towels, changes garbage, maintains the...
5 of 5 stars Reviewed March 31, 2014
We stayed with our yorkie, love love it. Very clean (although the bed was a bit uncomfortable) very clean staff was very friendly and helpful.five stars in our book we will stay...
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Hot Tub
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  • Pool
  • Satellite TV
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  • Suitable for children
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  • Elder access
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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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$288
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Suitable for children
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About this property
Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
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$258
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Suitable for children
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  • Elder access
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About this property
One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,... View all property information
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4 of 5 stars Reviewed June 5, 2014
This house is the perfect little hideaway. Close enough to Duval and all the action but far enough away that you can shut out the world and just relax. The hot tub is very...
5 of 5 stars Reviewed March 27, 2014
Leeward Isle is a great place to stay for a trip to Key West. It is within walking distance to all the hot spots and to the beautiful sunsets at Mallory Square, yet far enough...
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$148
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1 Bedroom, 1 Bathroom, 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
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  • 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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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Air Conditioning
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  • Smoking allowed
  • Suitable for children
  • x
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  • 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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3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Grill
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  • Private Pool
  • Satellite TV
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  • Suitable for children
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  • x
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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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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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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.