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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 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    3 of 5 stars (7) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 37
    4 of 5 stars (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    **Recently Renovated!! 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 days ago
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    4 of 5 stars Reviewed March 14, 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    1 / 30
    4 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 28, 2014
    We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location! Across...
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    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    OVERVIEW: Right in Key West -- NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's old house. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, Sleeps 2 | Quick View
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    About this property
    As the name suggests, the Garden House's 'Waterfall' rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West This cozy bedroom shares a bathroom with... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 4
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back in...
    5 of 5 stars Reviewed January 18, 2015
    Loved our stay in this very homely apartment. The location was excellent in the private Truman annex but close to Duval st and the local Green Parrot! The apartment was very well...
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    1 / 27
    4.5 of 5 stars (14) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    Booked M/V Coconuts as three of the party were used to being on the water, sailing backgrounds, so thought this would be different and it certainly was. Marvelous renovation of a...
    3 of 5 stars Reviewed November 30, 2015
    Air conditioning doesn't reach upper levels. Almost $600.00 taxes were a complete surprise.Enjoyed Key West & super boat races.
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 12
    2 Bedrooms, 3 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
    Location Information
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    1 / 8
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 9, 2015
    We rented this house with friends for about ten days. What a great place. We were only a few steps from Duval St and within 20 minutes walk of anything we wanted to do there...
    5 of 5 stars Reviewed July 17, 2012
    This house was great, it is a tad small but if your ok being in close quarters to split with some people its absolutly perfect. I traveled to Key west with my boyfriend as well as...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    About this property
    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 March 9, 2014
    Traveled with wife and brother and his wife. Very clean, nice size 1200 sf, convenient layout, Pool was nicely heated, adequate parking. about 3/4 of a mile from Malory Square...
    5 of 5 stars Reviewed August 12, 2013
    We have stayed here several times before but in another unit and the Dominica Retreat is much nicer. However we did kill 3 small roaches while we were there. We are planning on...
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    1 / 17
    4.5 of 5 stars (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This is one of the most elegant and colorful 2 bedroom units in the Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 26, 2014
    We stayed in this condo for spring break with our 9 and 15 year old. There was no smell on the small beach in front of condo. The condo is spacious, updated and very clean...
    4 of 5 stars Reviewed January 31, 2013
    We enjoyed our stay in this clean, attractive condo. It had all the amentities for a comfortable stay and a minor problem with the phone and internet service was resolved quickly...
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    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
    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $13,400
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    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 9, 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed February 26, 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    1 / 38
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 5, 2015
    This home is beautiful but a little TLC goes a long way. It would be nice if someone would give the outside pool area a good scrubbing. I'm not new to renting homes in KW and this...
    5 of 5 stars Reviewed March 10, 2015
    Excellent location, between Duvall and Simonton. Home is decorated nice. Very clean. We had two couples and had plenty of privacy. The pool is so nice and it was heated! Daily...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    Key West, Florida Keys 33040
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Banana Dream offers you exceptional value and an opportunity to enjoy Key West at its best! This is a charming 2 bedroom / 2 bath - first floor condominium. It is furnished with all of the comforts you would expect from a vacation home in paradise. Enjoy a frozen beverage while sitting in the... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous... View all property information
    Location Information
    Key West, Florida Keys
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Two bedroom, two bath, totally renovated in 2015, all new, marble floors, 10 foot ceilings, granite counters, walking distance to all major tourist attractions, one site parking, one block from Southernmost Point, one block from famous Duval Street. local beach is less than one mile, restaurants,... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests... 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
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
    About this property
    3 bedrooms, 2 full bathrooms, sleeps 6 Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for the ocean enthusiast. Choose to escape, relax and meditate by the waterfall or head out for a day of adventure on the high seas.... 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. 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 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going... 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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    About this property
    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
    Location Information
    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 / 12
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2015
    We went over the 4th of July weekend with a group of friends. Location is still amazing. The major concern was the it never felt as if the AC was cold enough. I am wondering if...
    4 of 5 stars Reviewed April 24, 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
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    1 / 25
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed June 7, 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
    5 of 5 stars Reviewed March 5, 2010
    The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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    1 / 15
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 2, 2015
    We traveled with a group of 4 couples and stayed in both cottages. We couldn't haven chosen a better location or better homes. These homes were in an awesome location on Duval St...
    5 of 5 stars Reviewed November 4, 2012
    House decorated nicely and very well maintained. Great pool and above average accommodations. Close enough to walk to everything at Mallory Square if you like a little exercise...
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    1 / 17
    4 of 5 stars (3) Very good
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. In the event you, your family, your guests, or your friends want to use the house at any time during... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 11, 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
    4 of 5 stars Reviewed November 28, 2011
    I rented The Main House at Bahama Gardens for a family vacation of about 10 days over Thanksgiving. There were 5 of us, myself, my husband, two adult sons and one son's...
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    1 / 7
    5 of 5 stars (26) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    $265
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    • Air Conditioning
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    • Waterfront
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    • Pet-friendly
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Click on my name 'Henry Karp' - just to the right of this paragraph then scroll down... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 27, 2015
    This condo is just what we were looking for. Nice large balcony to sit on and enjoy the view. Kitchen is full equipped with everything you will need, ie pots, pans, cups, plates...
    5 of 5 stars Reviewed July 23, 2014
    This was a great place to stay with my husband and four teenage kids. We all had plenty of room as the rooms were huge...even the bathrooms! Everything we needed was there...even...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... 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
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Writer's King is located at the end of our second floor balcony at our Key West lodging, located directly over the Lagoon where you can listen to our gentle waterfall on cool evenings. Featuring a King size bed with Tiffany reading lamps, the Writers' King is a relaxing way to enjoy your Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Hot Tub
    • Children's Pool
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    • Ocean Views
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    • x
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Recently updated 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... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (20) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 5 days ago
    Bahama House is located in a great location, just one block from Duval Street and a half block to the local grocer. Lovely shared backyard/pool area. Backyard and pool area well...
    5 of 5 stars Reviewed 4 weeks ago
    Just came home from a 10 day stay at Grand Bahama Suites. Had a fantastic time. Accommodations were excellent. Fantastic pool, bbq patio area awesome. Very clean yard and pool...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    About this property
    Downtown Key West, one block from Southernmost Point, one block from Hemingway House, walking distance to all mojor tourist attractions, restaurants, galleries, beaches. Three bedroom, two bath totally renovated, on site parking, rear patio. Central Air, granite counters, stainless appliances.... View all property information
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    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Double Delight is a large accommodation consisting of two double beds, a vanity and separate private bath. The Double Delight provides the perfect setup for couples, friends or family members traveling together during their Key West vacation. If you would prefer two bedrooms with a shared... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    About this property
    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly... View all property information
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    Key West, Florida Keys
    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    $5,373
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    • DVD Player
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    About this property
    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's 'Guestbook' column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 8, 2013
    Don't reserve at Olivia Cottage . . . because you may prevent us from doing so. We have traveled the world to just about every 5 star hotel of interest, and Olivia Cottage is the...
    5 of 5 stars Reviewed July 21, 2011
    I stayed in Olivia Cottage five weeks and loved every minute. After looking at pictures on the internet, I felt like I was stepping into the pictures. It's exactly as shown. The...
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    6 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    3.5 of 5 stars (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 15, 2009
    This was the second year we rented this house for the month of October. We head up a krewe that puts a float in the Fantasy Fest parade. We also sponsor and co-sponsor several...
    5 of 5 stars Reviewed June 18, 2009
    We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful...
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    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $5,200
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    • Porch
    • Satellite TV
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    • Pet-friendly
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    • ?
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 2, 2015
    My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for...
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    1 / 37
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    $488
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    • x
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    About this property
    Hibiscus Suite is a queen efficiency with a kitchen, bathroom and a small outdoor deck. Orchid and Jasmine are both one bedroom suites with queen bedrooms, queen sleeper sofas, kitchenettes and outdoor decks. All units have TV/DVD, cable and Free WiFi! This complex offers combined parking for 3... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 30, 2014
    Lovely we'll maintained, self catering, semi-detached apartments which allows privacy yet accommodates large extended family barbecues and mingling. We hired 3 of the apartments...
    5 of 5 stars Reviewed July 28, 2014
    Pictures online are great and the property was perfect for 3 families traveling together. We tried not to be in rooms during the day since we were busy with excursions but the...
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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.