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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 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 22
    4.5 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
    5 of 5 stars Reviewed March 2, 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with... View all property information
    Location Information
    Key West, Florida Keys
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 stars (5) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 11, 2015
    This place was fantastic!! We all loved it and plan to come back and rent this property again. The staff was friendly and was fast to respond to any of our needs (and there were...
    4 of 5 stars Reviewed April 15, 2015
    This is two fairly large apartments above what i assume is the main office for VHKW. The house entrance leads you up a nice wood floor staircase to the 2nd floor apartments. One...
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    1 / 37
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    'South Street Serenity' This light and airy 3 bedroom, 2.5 bath home has a wrap around deck and expansive French doors that lead from every ground floor room to an outdoor space. Enter the private gate and you will be in a tropical paradise, surrounded by lush palms, fiery bougainvillea, and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 29, 2015
    Phil our Concierge was great getting anything we wanted done like fishing/snorkeling trips scheduled, light bulbs fixed etc. could not say enough about him. The house is a dream...
    4 of 5 stars Reviewed April 29, 2014
    the service we received from Carlos the property manager from south street serenity was excellent. whenever we had a question he either answered the phone or called us back...
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    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 19, 2015
    Sweet 2 bedroom 2 story condo at Truman and Simonton - just a block from Duval street! Great privacy for two couples (my husband and I and our daughter and son in law) because...
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    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 25
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard’s Perch is a great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed September 18, 2014
    Highly recommend this facility to anyone who is looking for a conveniently located, quiet, easily acessable 2 bedroom / 2 bath condo. Our week stay was everything we could...
    5 of 5 stars Reviewed May 12, 2014
    Three friends that I have known since first grade and I traveled to Key West for a week to celebrate the year we all turn 60. Stayed at Shipyard Perch. it was perfect. The 2...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Paradise at its finest is exactly what you can expect from this exquisite and unique home. Sunset Key Overlook is a stunning two bedroom, two and a half bathroom house on a private island, in Key West. Enjoy access to private owner’s beach on western facing side of island with beautiful sunset... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Lovely studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to it's fullest in this highly desired walking... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 30, 2015
    Nice neighborhood, close to water. Attentive property concierge. Just a few blocks from water and many great bar and grills. Cozy studio.
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    1 / 23
    5 of 5 stars (3) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 14, 2015
    Clean, bright, new grills, apts stocked, perfect location, beautiful private pool. 6 private apts, contacted the owner with a few questions, she answered immediately. I would rent...
    5 of 5 stars Reviewed July 28, 2015
    A group of our great friends and family decided to spend a week in Key West for some diving and partying. Our requirements included 1) a clean place, 2) convenient to Duval St...
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    1 / 26
    4.5 of 5 stars (8) Very good
    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 superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 30, 2013
    What could be better in Key West than your own pool, adorable kitchen and updated baths, and a great location, a few blocks from Duval. Kw Vacation Rentals couldn't have been...
    5 of 5 stars Reviewed December 23, 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    LUXURY Vacation Home located on Millionaire’s Row in Historic Old Town Key West We guarantee that the Coral House will fulfill even the highest expectations. Just under 2000 square feet of indoor living area: This beautiful home is filled with amazing local artwork and has the Tropical feel... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 3, 2015
    Wonderful location--close to excellent neighborhood restaurants and recreation. The house is beautifully decorated and very comfortable for adults. We have visited Key West for...
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 14, 2015
    Location was superb. Staff at Compass / Truman Annex Reality (Michelle) were easy to work with and very accommodating. Owner was very pleasurable and great to work with. Overall...
    5 of 5 stars Reviewed May 13, 2015
    Fully equipped, comfortable, clean, family home with the use of a community pool. During our stay in May (when it was very warm) there were only ever a few at the pool which was...
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... 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
    Room 2's pale shade of coral will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private bathroom... View all property information
    Location Information
    Key West, Florida Keys 33040
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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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    About this property
    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week 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 / 30
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 10, 2014
    Location of Tobago house is excellent if you like to be close to restaurants, beach, and all that key west has to offer. Leave your car at home as parking is difficult. The house...
    4 of 5 stars Reviewed March 12, 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
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    1 / 26
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 7, 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    5 of 5 stars Reviewed August 6, 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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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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    1 / 25
    1 of 5 stars (1) Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided. This property will meet all of the demands a... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 5 Bathrooms, Sleeps 4 | Quick View
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    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 15, 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
    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...
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    1 / 24
    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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 / 17
    4 of 5 stars (3) Very good
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    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
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    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 / 14
    4.5 of 5 stars (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 19
    4.5 of 5 stars (8) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 2, 2015
    We stayed at Penthouse on Duval for a week, renting the entire unit (4 Bedrooms and 4 1/2 baths) and it was absolutely as described including the pictures. It was large...
    5 of 5 stars Reviewed June 30, 2015
    This place was absolutely perfect. We came down and stayed with 10 of our closest friends and family for my mother-in-laws 70th birthday party. The place was beautiful and the...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 30, 2014
    This was a fantastic place to stay - I would definitely recommend it! The location is great - at the north end of Duval Street, just blocks from the beach. The cottage was very...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View Florida Keys condo for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. Located on the Atlantic Ocean... 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
    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 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Construido en la década de 1950, el complejo rezuma encanto de la época, sin retraso en el crecimiento de las comodidades. Las habitaciones cuentan con obras de arte cubano, TV de pantalla plana, mini-nevera, y hamacas. El hotel presta huéspedes coloridos sarongs para relajarse, y algunas... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4 of 5 stars (25) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 9, 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the town...
    4 of 5 stars Reviewed June 30, 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
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    1 / 20
    5 of 5 stars (25) Excellent
    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 Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 8, 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 stars Reviewed August 19, 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    1 / 28
    4 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 the... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 9, 2015
    This was not as I expected. The place is very clean. Here are my things that I as not expecting. U can not go right to the beach in front of this place all rocks. Smothers beach...
    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...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • 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
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • 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
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 stars (50) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed December 16, 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You will...
    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.
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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
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    Key West, Florida Keys 33040
    1 / 31
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    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 (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 29, 2015
    What a fabulous place to stay. Very clean and modern. All the comforts of home. Very close to the action. Was able to walk to all events at Key West. Highly recommend.
    5 of 5 stars Reviewed June 14, 2015
    Clean and sunny 2 bedroom apartment with fully equiped kitchen, only 1/2 block from grocery store and restaurants. We walked to everything, though there is a driveway for off...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor.... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 stars (15) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 2, 2013
    After reading great reviews about the Villa Tropicale, we rented this property for six nights last month. We were traveling with a group of eight and wanted a large home where we...
    5 of 5 stars Reviewed January 27, 2013
    This was not our first stay at Villa Tropicale and we certainly intend to come back. When we first opened the gate of the property a few years ago, we were delighted to discover...
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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.