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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 stars (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (22) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 22, 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 22
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 5, 2015
    My Husband, I and my sister spent 6 days in Key West. This was a home like condo to stay in. It had a kitchen,dining room and living room on the main level with a bathroom(all one...
    4 of 5 stars Reviewed April 8, 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 15, 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
    5 of 5 stars Reviewed March 5, 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
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    1 / 13
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    Tom from Duval Balcony was wonderful. He communicated with me to confirm my visit and then to make arrangements to meet when it was time to check in. When we arrived he...
    5 of 5 stars Reviewed October 22, 2015
    Being a Florida local, I travel to Key West quite often for the past 13 years and have never had a better and more pleasant stay than at the Duval Balcony. The owner was waiting...
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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 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 18, 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 stars Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 12
    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 9, 2016
    I stayed here for 2 days this summer. My 2 adult son's, daughter in law and grand baby. Overall quiet area, very easy to get around, didn't have a chance to swim in the pool. We...
    3 of 5 stars Reviewed May 31, 2016
    This condo was very large and we could spread out as a family, which is great when you have two teenagers. The beach in front of complex is tiny and not really usable for...
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 stars Reviewed October 25, 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 23, 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group had...
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    1 / 99
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed November 9, 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
    5 of 5 stars Reviewed July 20, 2015
    Great place to sleep-we spent most of the time touring-courtyard was great for meeting new friends-place was very clean and plenty of space for 3 couples-location was very...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 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 9, 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    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...
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    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 4, 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed December 15, 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    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 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    • Shared Yard
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    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (44) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 21, 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
    5 of 5 stars Reviewed October 26, 2014
    We had a wonderful time staying at Osprey and will reserve this cute little place every time we go to Key West. The location on Olivia St is ideal for getting to all the action...
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    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 26, 2016
    This great rental was even better than advertised. It offered total peace and privacy with the private back yard and pool, and cottage with a second bedroom and outdoor shower...
    5 of 5 stars Reviewed January 18, 2016
    My husband and I stayed with friends at this beautiful home (Oasis lives up to its name). Our friends who we were traveling with had been to Key West many times, but this was our...
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around Wilmington town or shopping, eating and drinking your way down to the board walk on front street .... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
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    Key West, Florida Keys 33040
    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed October 14, 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
    5 of 5 stars Reviewed June 26, 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 8, 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    1 / 27
    4 of 5 stars (13) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    CORAL SUITE: 2 bedroom 3 bath townhome for 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master bedroom has a private balcony. Guest bedroom is roomy and private. The Murphy bed in the living room is sturdy and comfortable. Kitchen is equipped with all... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 10, 2014
    There were 4 in our group (family), and we had a lovely time! It was a bit difficult to find, especially for the pizza delivery man...lol Despite Tropical Storm Issac, we had a...
    5 of 5 stars Reviewed April 17, 2014
    I am a seasoned visitor to Key West. Over thirty visits thus far. This was the best way to spend a week on the island. Everything was superb. Nothing was out of place...
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    1 / 5
    3.5 of 5 stars (2) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    Live in luxury poolside in a beautifully furnished studio (private room and full bath) apartment, situated in a quiet, coveted residential Key West neighborhood. Walk right outside your door into an enchanting, very nicely landscaped pool/deck area for your enjoyment. You'll be strategically... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 2016
    From the moment we arrived into the tropical lush forrest, which enclosed the pool and property, we knew we were in paradise! We were pleasantly greeted by Chuck, the owner & his...
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    1 / 35
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 28, 2016
    First time using a Vacation Rental & forst time in Florida so wasn't sure what to expect, walked into the Condo and it was beautiful, well kept, and tastefully decorated. Loved...
    5 of 5 stars Reviewed April 23, 2016
    This condo was like being at home. The attention to detail for items you need when traveling were there for our use. Beach towels, beach chairs, and even beach toys for children...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Ocean Views from Every Balcony. Expect every Amenity from Hyatt. Come Relax by the water with a cool drink. Come visit Old Town Key West for the Sunset Celebration on Mallory Square while enjoying the entertainment, dining and shopping along Duvall Street. This historical city has much to see &... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 stars (11) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and off-street parking for... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed April 10, 2014
    Rent this condo if you are looking for a place out of the fray but nonetheless close. It is 10 - 15 minutes to Duval Street, and very bikeable. Stock Island eateries (Roostica...
    4 of 5 stars Reviewed October 10, 2013
    A group of 7 of us stayed here for 4 days and it was a very nice time. There was a slight shortage of towels but there was a washer and dryer that was fast and easy to use in the...
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 9, 2016
    We felt at home the minute we walked in. Very quaint and clean. Everything you needed. The only negatives were that the house is located on a very busy street so there was quite a...
    5 of 5 stars Reviewed June 15, 2015
    The owners could not have been nicer. Clean, right downtown, close to all the action in town. Going to make it back and stay here again.
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    1 / 21
    4 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 11, 2016
    4 bed/4 bath older/historical home. Some of the rooms lacked storage space but they were clean and beds/bathrooms were good. Two good size bedrooms and the other two not much...
    5 of 5 stars Reviewed April 4, 2016
    I rarely get on sites to complete a review. However, I felt that this review needed to happen, as I was looking for current reviews of the property when we were looking for that...
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    1 / 24
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has a private balcony.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 6, 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
    5 of 5 stars Reviewed February 26, 2014
    Loved Duval Breeze! The house was bigger than the pictures depicted and it was so comfortable. Having not only towels and linens available but also basics like toilet paper and...
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    1 / 39
    4.5 of 5 stars (29) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine with ocean breezes wafting by. Condo offers street view; complex offers ocean... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 29, 2014
    With a short walk to the beaches, the awesome pool and hot tub, and quick drive to Duvall Street, this was the perfect place to stay! Our condo was so clean and spacious and we...
    5 of 5 stars Reviewed April 12, 2014
    We love the location next to the beach. The pool and hot tub were clean and a perfect temp. The rental was very clean and well equipped. We bought more toilet paper and could...
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    1 / 22
    4.5 of 5 stars (83) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    BAHAMA DREAMING: One Of At Home In Key West's Most Popular Rentals! Bahama Dreaming is a traditional 3-bedroom Conch cottage located just steps from Duval Street. With it's fantastic location and amenities this home offers it all. The main level has 2 bedrooms, one containing a comfy queen size... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 weeks ago
    We have just returned from our yearly girls trip to Key West. We are a group of 6 women in our late 50's (60's) who visit every year in June for a week of fun. First, let ,e...
    4 of 5 stars Reviewed April 18, 2016
    We enjoyed our stay at Bahama Dreaming. The house was very clean and comfortable, well stocked with kitchen items as well as plenty of beach towels. The pool was small but clean...
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    1 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 3, 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    5 of 5 stars Reviewed December 18, 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    1 / 22
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    CORAL GARDEN: 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock. Fully-equipped kitchen, comfortable dining area, and living room sports a gigantic 52" HDTV for your viewing pleasure. Master bedroom with bath ensuite offers a comfy queen bed; 2nd bedroom with bath ensuite... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 12, 2013
    Our visit to Key West was amazing. At Home in Key West Inc. has the best services they were very informal and personal. At Home made sure we had everything that was needed for our...
    5 of 5 stars Reviewed August 16, 2013
    We were thrilled to see that the home was so well kept and looked exactly like the photographs. I would definitely recommend people staying here especially if you have children...
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    1 / 18
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic Ocean is only 4 blocks away. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 21, 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
    4 of 5 stars Reviewed March 19, 2014
    We loved Tropical Dreaming! The location is excellent, just two blocks from Duval and a few blocks from South Beach and practically in walking distance to everything. The home is...
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    1 / 19
    4.5 of 5 stars (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 17, 2016
    This place is very nice and has all the convenience's of home. Located one block off of Duval street so you can walk Duval, drink and not have to drive home. The weather was...
    5 of 5 stars Reviewed May 14, 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 stars (1) Excellent
    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 in a secluded cul-de-sac in Truman Annex, a pristine gated community located in historic Old Town Key West is walking distance of anything you will want to do during your visit. The formal entrance of this vacation rental... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 4, 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
    4 of 5 stars Reviewed December 5, 2013
    Very nice 2 bedroom 2 1/2 baths located in an excellent location. Walk right down to Duvall Street. Located at the quite end of Duvall. Great accomdations but a bit pricey.
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 3, 2014
    The condo was exactly what I was looking for and it was represented accurately. It was about fifteen minutes from Duval street, had a water view, it was quiet and the interior...
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    1 / 27
    5 of 5 stars (52) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 18, 2015
    Shipyard Treasure is welcoming, comfortable, condo, decorated with Key West art in the bedrooms, living room, and entry, and with wonderful beds, bedding, and much better than...
    5 of 5 stars Reviewed March 16, 2013
    My family had a wonderful vacation while staying at the Shipyard Treasure. The condo was tastefully decorated and was stocked with all the comforts of home. The location was...
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    1 / 27
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 13, 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
    5 of 5 stars Reviewed April 3, 2015
    We had an incredible time at the Bahama House in Key West. We were in town for my sister's wedding and our party included my parents, my wife and two young children and my sister...
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    1 / 24
    4 of 5 stars (28) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    PAPAYA PLACE: 2 bedroom 2 bath condo at 1800 Atlantic Blvd. with garden view overlooking the nature preserve. Master bedroom with new king bed and bathroom ensuite; twin beds in guest bedroom with full bath across the hall. WIFI, unlimited long distance calls,3 flatscreen TVs and expanded cable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 8, 2016
    My wife and I have been staying at Papaya place for years and it just gets better! The beautiful colors and homey touches are our favorite. It is always immaculate when we arrive...
    5 of 5 stars Reviewed May 26, 2016
    This very pretty and comfortable condo was in a great location - access to the beach, very close to the airport and a five minute cheap cab to Duval Street. The condo is very...
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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.