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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 16
    4.5 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 35
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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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    Key West, Florida Keys 33040
    1 / 21
    4.5 of 5 stars (35) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 8, 2014
    We had a large group visiting Key West for the Swim Around Key West annual event. We had plenty of space for all 10 of us to sleep comfortably. The washer and dryer were very...
    5 of 5 stars Reviewed September 18, 2013
    We had a great time. The rental unit was very nice. We were in town for a wedding and it worked out great for us. If your coming down with a boat this would be a great place. If...
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    1 / 20
    3.5 of 5 stars (9) Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed March 3, 2015
    The property could use some updating. A little paint and some updated furniture would do wonders. Towels without rust and bleach stains should be considered. But we are used to...
    3 of 5 stars Reviewed December 14, 2014
    My family (a group of 9) stayed here for a week while in Key West for a wedding. Amelia's Hideaway was...ok. The rooftop deck and poolside patio were perfect for sitting outside...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    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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    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (41) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
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    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    This rental was everything that it said it was and more. The place was actually more spacious than I thought it would be. Everything about it was first rate and beautiful. The...
    5 of 5 stars Reviewed 5 weeks ago
    Only the weather didn't cooperate, still had a great time and the place is beautiful. Would definitely love to return in October this year.
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    1 / 23
    5 of 5 stars (19) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Very private gated compound right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing outside the gate, on... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 25, 2015
    My husband and I, and three other couples came to Key West for a friend's wedding. After much research, I am so thankful to have come across Harbor Walk Hideaways. The grounds...
    5 of 5 stars Reviewed October 13, 2015
    We, 8 adults in their early 50's, stayed here for 4 nights. We loved it. You walk down the street, unlock your private gate and walk back through a tree lined path to your oasis...
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    1 / 34
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed January 4, 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    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...
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    1 / 26
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 29, 2015
    We came in a small plane, so we needed to ship our luggage down to Key West. The office staff allowed us to ship it right to the check in office. The suite had two rooms and a...
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    1 / 21
    4.5 of 5 stars (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 31, 2015
    We found this place very cozy and well located. It was clean and very spacious for two people. The air conditioner wall was a little noise, but it didn't bother us much because we...
    4 of 5 stars Reviewed June 4, 2015
    More space than a hotel room for less money than we usually pay. Convenient location to Duval. Quiet neighborhood. No closet door, beads hanging instead. When air conditioner...
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    1 / 22
    4.5 of 5 stars (29) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 17, 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent selection...
    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...
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    1 / 26
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 18, 2015
    We had a group of girls and we wanted to be close to Duval but also have a pool. The pictures almost don't do it justice. It was awesome. The beds were very comfortable. Two...
    5 of 5 stars Reviewed May 28, 2015
    Helen's Hideaway is a great little hideaway in Key West. It is very private and has parking which is an added bonus. Inside the house it was clean and we had maid service every...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. Newly painted, 'Barely Teal', this room highlights a four-poster bed. The recently remodelled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the... View all property information
    Location Information
    Key West, Florida Keys 33040
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    About this property
    A hidden jewel in the old town of Key West. A private garden, with pool, and fountain, covered porch, and space to sun. Comfortable bedrooms, with a loft to sleep 2. fully equipped kitchen, air-conditioning internet, tv, cable. Bes quiet neighborhood. This home rents by the month and is occupied a... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
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    3 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
    • Ocean Views
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    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
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    Key West, Florida Keys 33040
    1 / 39
    4 of 5 stars (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 22, 2015
    We just spent a week at SMR and really enjoyed our stay! Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
    4 of 5 stars Reviewed November 23, 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub which...
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    1 / 31
    4.5 of 5 stars (39) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 4, 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    3 of 5 stars Reviewed February 28, 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ***BRAND NEW POOL COMPLETED SEPTEMBER 2015*** Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
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    About this property
    Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed September 27, 2015
    We found the unit on FlipKey but it is managed by Historic Hideaways. Historic Hideaways was easy to deal with. I made the reservation by phone but the rest of the stuff was done...
    5 of 5 stars Reviewed March 4, 2015
    We have stayed in Key West several times now, but the Campbell Suite has been by far the most ideal rental. It is central walking to almost anywhere that you would like to go...
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    1 / 70
    3 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This popular island destination is the site of the only living coral reef in the coastal regions of the US. In addition to the marine life and water activities other features of Key West include natural preserves and unique land animals. Coconut Mallory Resort and Marina is located in Key West,... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed November 19, 2015
    Toilet had issues, second beds mattress should have been replaced as it was soiled. Accommodations are average but the staff was excellent and easy to deal with. Wifi was spotty...
    5 of 5 stars Reviewed November 17, 2015
    Love this place, quiet side of Key West but close enough to down town & Duval st. fun. We have been coming here since 2008 and they work hard on the place and every year we come...
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    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
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    Key West, Florida Keys
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This nightly group rental consists of 3 separate units Porchside Paradise, Orange Blossom Suite, Deckside Suite. Three separate bedrooms with queen sized beds. Two sleeper sofas and two private hot tubs! Located at 510 Petronia St, literally steps from Duval St! Take advantage of the vivid... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 30, 2011
    Newton Street remains a peaceful enclave - hard to believe it is situated between busy White and Truman streets. The interior was immaculate, as always, and it only took about 20...
    5 of 5 stars Reviewed June 17, 2011
    We have stayed at the Newton Street Hideaway for several years, and, as soon as we open the door, it's just like coming home! It's fun to spot the improvements made by the owners...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.  Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    4 of 5 stars (14) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed April 8, 2014
    The house is as described. Clean and comfortable. The condo is very pleasant and safe. Pool was very much appreciated by our children. The main inconvenient is the noise. The...
    5 of 5 stars Reviewed May 19, 2013
    This place was phenomenal! A gorgeous, well-furnished, well-kept condo! It has three FULL bathrooms, 3 large bedrooms, the MBR upstairs has a nice tub and a standalone separate...
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    1 / 28
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 15, 2015
    We stayed here March 10th - 12th and found the unit very clean and comfortable. The location was right for us as it is on the quiet end of Duval street, but close enough to bike...
    4 of 5 stars Reviewed March 11, 2015
    It was well equipped. Sometimes the parking was a pain but at least we had parking. The worst part was the patio was unusable because of noisy air conditioner. And no closet in...
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    1 / 19
    4 of 5 stars (6) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer. Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 8, 2014
    Super-cute house, adorably decorated, with nice bathrooms & a great Viking range for when you're eating in. Great location in Bahama Village.
    5 of 5 stars Reviewed December 26, 2013
    Fishtail Hideaway is located in a quiet neighborhood only 2 blocks from Duval St. We loved being able to walk to the beach, the Southernmost Point, plenty of shopping and the...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Share space in the 2bedrooom 2 bathroom apartment in the New Town of Key West. It will be Private Room with bathroom for you. Free WI-FI internet, free parking, queen size bed. Apartment is located in a very quiet location. If we are available we can pick you up from the airport and ferry station.... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony... View all property information
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    Key West, Florida Keys
    1 / 54
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Share 5 Star $2.4m Beautiful New Large modern Home on very quiet street in Old Town of Key West. Advantage is Location, Location and Location! Own fully furnished bedrooms with Queen size bed for 1 - 2 (see photos) with 32' flat screen TV and 2 french doors leading onto private balcony... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 19, 2015
    Lovely air conditioned home well located for all of Key West amenities. Quiet and well designed and furnished. Great host, very accommodating. We had a ball. Liz & Graham
    5 of 5 stars Reviewed April 2, 2015
    We were out a lot, biking, visiting and eating. However, each time we came back to Don's place it felt welcoming and friendly. Don is a delightful host. The bedroom with...
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    1 / 30
    4 of 5 stars (39) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 8, 2013
    We had seven guys from four states converge here for my bachelor party, and I cannot say enough about this place. I didn't experience any of the symptoms of what the bad reviews...
    5 of 5 stars Reviewed September 3, 2013
    We were not vacationing; we were working and the accommodations were very good for us. We wish we had more time to enjoy it. Thanks for being so accommodating and helpful! Tammy...
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    1 / 26
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ************************************************************************************************************************ ************************************************************************************************************************ Wake up to the sun rising over the sparkling Atlantic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 27, 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
    5 of 5 stars Reviewed November 4, 2015
    We had such an amazing time in the Florida Keys. Staying at Atlantic Sunrise was icing on the cake. The condo is beautiful and the owners were so very kind! The notebook with...
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 4 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time! Palm... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4 of 5 stars (14) Very good
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Located at Papa's Hideaway Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling through the palms, blowing each of your cares away... This Deluxe Studio is located on the ground floor and offers a private porch just off of the pool area. The unit... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed September 19, 2015
    The setting is very secluded yet only two blocks from Duval Street. The main house is very nice with 2 bedrooms, 2 baths, kitchen, dining and living room. A porch surrounds 3...
    4 of 5 stars Reviewed June 4, 2015
    By far the best part about our stay was the pool. It was so great to have somewhere to relax while we were in Key West. That's the whole point in going! The pool was the perfect...
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 7
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    This condo is absolutely amazing!! The pictures on the web site are exactly how it looks when you walk in. The bedrooms are large with a bath off each. A large walk in closet...
    5 of 5 stars Reviewed November 19, 2015
    Our room exceeded our expectations in every way. All of the appliances were brand new, the paint was fresh and every part of our apartment was spotlessly clean. I can't wait to...
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    1 / 19
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 26, 2015
    Absolutely could not have found a better location and within easy walking distance to the most visited areas of Key West. So good that one night we took the car out but could not...
    5 of 5 stars Reviewed September 23, 2015
    Jack Agnew is the BEST! It was such a pleasure working with Jack on all aspects of our trip to his cottage and Key West. It was our first trip and we could not have picked a...
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    1 / 28
    4.5 of 5 stars (48) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 2 weeks ago
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while the...
    3 of 5 stars Reviewed December 2, 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4 of 5 stars (32) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed October 16, 2015
    This condo was a bit dated and could a little TLC, but overall worked great. The location was nice on the water and was not too far from downtown. Everything worked really nice...
    4 of 5 stars Reviewed September 4, 2013
    Stayed at Pelican Landing in a group of 8. The interiors were all nice and comfortable with clean bathrooms and kitchen. Beds were comfortable and sheets were clean, sofabed was...
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    Key West Vacation Rentals and Condos

    Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!

    Of course, it’s not all limes and leisure. Phenomenal water activities and outdoor recreation are just steps from your vacation rental, while kid-friendly adventure parks are abundant. The social scene on Duval Street caters to both a younger and older clientele looking to mingle over mouthwatering cuisine or tantalizing cocktails.

    Condo rentals in Key West are so enticing that the island is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and it’s been home to literary greats Ernest Hemingway and Tennessee Williams.

    Where To Rent a Vacation Home in Key West

    Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. 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.

    Many House Rentals Near Attractions and Activities For All Ages

    Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.

    Key West Bars and Restaurants

    Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. 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.

    Book a Key West Vacation Rental For Your Next Trip

    Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.