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House Rentals in Key West, FL

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    Travellers 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 22 August 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 2 May 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 5 July 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 8 April 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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    • Satellite TV
    • Balcony
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    • Terrace
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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 15 April 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 5 March 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 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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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 18 September 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 25 May 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 / 13
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
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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 2 weeks 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 22 October 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 / 12
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Balcony
    • Internet Access
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    • Outdoor Dining Area
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    We LOVED this condo for our stay in Key West. The condo was very clean, spacious, absolutely adorable, and most importantly affordable! It was nice to have access to a pool and...
    5 of 5 stars Reviewed 9 June 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...
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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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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 9 February 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 29 December 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 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • ?
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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 10 February 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 25 October 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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    • Satellite TV
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    • Private Garden
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    • Pet-friendly
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    • x
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    • x
    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 23 February 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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    • Patio
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    • ?
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    • x
    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 9 November 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 20 July 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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    1 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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 9 March 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 18 March 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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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 4 January 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 15 December 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    • ?
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    • x
    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 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Air Conditioning
    • Shared Garden
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    • Pet-friendly
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    • x
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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 24 September 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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    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
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    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 26 January 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 18 January 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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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    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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    • ?
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    • x
    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
    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
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
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    • Mountain Views
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    • x
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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
    Location Information
    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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    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 14 October 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 26 June 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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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    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 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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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 8 December 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 / 5
    3.5 of 5 stars (2) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 April 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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    About this property
    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 28 April 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 23 April 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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    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
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    Key West, Florida Keys 33040
    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 9 April 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 15 June 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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 11 April 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 4 April 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 / 38
    5 of 5 stars (36) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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 3 January 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 18 December 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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    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
    Location Information
    Key West, Florida Keys 33040
    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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    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 3 May 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 (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 17 March 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    5 of 5 stars Reviewed 15 March 2016
    This is our second visit to this rental, (we were there 3 yrs ago). We brought friends and family along, and all loved the villa. Two houses with a shared grotto with all the...
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    1 / 29
    5 of 5 stars (38) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 December 2015
    This is a most beautiful home! Perfect for our 10 family members. The kitchen is fully equipped for all family needs. Each bedroom is beautifully decorated with its own theme...
    5 of 5 stars Reviewed 20 August 2015
    This is a great house with plenty of space for a large group. House is fully stocked, big rooms and comfortable beds. Conveniently located to all of the attractions. Sharon is...
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    1 / 28
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 20 March 2016
    Very nice condo. A little far from the action but totally enjoyed bike riding all around the island, with the bikes provided by John. John was a great owner helping and...
    5 of 5 stars Reviewed 28 October 2014
    fabulous condo on a very secure property close to the beaches. Roosevelt Blvd is within walking distance and has a sidewalk large enough for walking and biking along the ocean...
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the area including... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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    Key West, Florida Keys 33040
    1 / 5
    4.5 of 5 stars (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Nicely furnished private room and bath in quiet, desirable neighborhood in Old Town Key West. A/C + Cable TV + WiFi. Access to enchanting, large pool/deck area with outside grill. Equipped with microwave and refrigerator. The pool/deck area is beautifully landscaped and available for your use.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 30 December 2015
    We had a great time in Key West. The rental was conveniently located about five blocks from Duval Street in the quieter side of town. The rental was clean and cozy ... perfect for...
    5 of 5 stars Reviewed 8 November 2015
    This was our first experience using Flip Key and could not have been any more pleased. At the time our booking, the host, Chuck communicated all the specifics and we felt...
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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 / 12
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 7 July 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 24 April 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 November 2013
    I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 26 February 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...
    5 of 5 stars Reviewed 28 May 2013
    Hemingway's Retreat was more than we could have hoped for! The house was beautiful, the location was perfect, and the pool was awesome for our family. The owner was fantastic to...
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    Key West Vacation Rentals

    Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

    Where to rent in Key West, Florida

    Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

    Key West Bars and Restaurants

    Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

    Sightseeing and Activities in Key West

    Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.