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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 5
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 11
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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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
    4 of 5 stars Reviewed 28 July 2015
    Everything you need, easy to get around island. Quiet, no view of water. Great place for the price. I would stay here again.
    4 of 5 stars Reviewed 25 March 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
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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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    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 / 13
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
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    • Porch
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    • Balcony
    • Patio
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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 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...
    5 of 5 stars Reviewed 21 October 2015
    We stayed here in July and it was just what we were looking for. Pretty roomy for Key West, very clean and well kept, and right on Duval St. When we wanted to go out to eat, drink...
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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
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
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    • Pet-friendly
    • Wheelchair access
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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 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    About this property
    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 / 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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    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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    1 / 9
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    You have use of one of four private cabins with a private marine style bathroom. Three cabins available for rent. You will share the common areas with new friends. The cabin is air conditioned with a queen like bed. Captain Charles and wife Deborah use one cabin. When conditions allow we offer a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 29 May 2015
    Five of us stayed on the Anna B over the weekend. It is a very nice catamaran sailboat, clean and well maintained. Each stateroom had fresh linens, its own en-suite bathroom, and...
    5 of 5 stars Reviewed 28 May 2015
    Our stay was wonderful! It's was clean, quaint & relaxing! I hope to return soon. Captain Charles was a pleasure to speak to!
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    3 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Hot Tub
    • Children's Pool
    • Waterfront
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    • Satellite TV
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    • Wi-Fi
    • Sauna
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    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West This place is really incredible! it's one of the largest ocean front suites in Key West. 3 bed room, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony affords 90' of unobstructed... View all property information
    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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    • Patio
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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 2 weeks ago
    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 3 weeks ago
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    If only for a short time, gift yourselves the opportunity to experience life as a Key West yachter. This 42’ fully equipped blue water cruiser, docked at the Stock Island Village Marina affords you a “Dockside” overnight rate either before or after a scheduled Tortuga Sailing Adventure charter. A... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
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    • Patio
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool 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 and... 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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    • DVD Player
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light... 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... 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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    • Hot Tub
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    • Pet-friendly
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    About this property
    KEY WEST VACATION CONDO RENTAL DESCRIPTION Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor. It is approximately 1200 sq ft... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 25 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Ocean Views
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    • x
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    About this property
    3 bedrooms, 2 full bathrooms, sleeps 6 Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for the ocean enthusiast. Choose to escape, relax and meditate by the waterfall or head out for a day of adventure on the high seas.... View all property information
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    Key West, Florida Keys 33040
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    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 September 2015
    Located in the historic Old Town section of Key West, this is one of three units in one building. The owner lives in the front and their friend in the middle unit, both were very...
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    1 / 26
    5 of 5 stars (27) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 30 November 2015
    We loved our stay at Casa del Sol. The location was perfect for sight seeing and walking everywhere. We never used our car for the week's stay. The beds were comfortable, the...
    5 of 5 stars Reviewed 31 August 2015
    Casa del Sol is in a perfect location in Key West with an easy 2 block walk to Duvall Street but in a quiet relaxing residential area. The condo is very clean, well equipped and...
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    1 / 22
    4.5 of 5 stars (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 September 2013
    We have been renting a condo at this property for many years under different mangement companies and the folks managing it now are top notch the are doing a great job
    4 of 5 stars Reviewed 31 July 2013
    The location was perfect for us since we had a boat and the rental came with a boat slip. Our balcony even looked down on our boat. Room space was very adequate for the eight of...
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    1 / 23
    4.5 of 5 stars (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 24 July 2013
    I have been staying here since 1985, recent property improvements have been added. Units are in good shape and clean. The best place in Key West if you have a boat and need to...
    5 of 5 stars Reviewed 13 July 2013
    We love staying at Pelican Landing while visiting Key West. We usually stay on the 2nd floor, though the Antigua suite was nice. The only comments are the suite is in need of...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This is a House Boat that is 45 feet long and 18 feet wide two story. The Boat House is located Sunset Marina over looking the Gulf Of Mexico. Fisherman paradise and couples paradise. You are just minutes for all of Key West excitement. The marina is very quite and the water is crystal clear. You... View all property information
    Location Information
    Key West, Florida Keys KEY WEST FL 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Cozy Studio In Great Location Additional amenities include: kitchenette, sundeck, close to art galleries, large wrap around deck, daily housekeeping, nightly rental, near southernmost point, close to downtown bars. View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 stars (30) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This immaculately clean and comfortable well air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a new Queen Sleeper Sofa with gel memory foam mattress. The efficiency... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 1 December 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several cracked...
    4 of 5 stars Reviewed 17 November 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The name of this one-bedroom, one full bath condo suggests the most persistent legend of Key West: that vacationers come for a week and stay a lifetime. Located in the prestigious gated Truman Annex community, this unit is the perfect place to try out island living for yourself. From its fabulous... View all property information
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    Key West, Florida Keys
    1 / 12
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    About this property
    Two Bedroom Premiere Ocean View This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. You cannot get a better view than this. King bed in the master and a queen in the 2nd bedroom. High speed wireless internet access. There is a full size fully equipped eat in Kitchen. Full... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    We went on a family vacation in may 2013 to the Keys and decided to say in the condo because of the great location to the beach. The condo was very clean and had everything we...
    4 of 5 stars Reviewed 18 September 2010
    December 2009 was our fifth time staying at the 1800 atlantic condo. My husband and I are anticipating our stay this year as it is the best value for our dollar. Julia at all...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and many... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just... View all property information
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    Key West, Florida Keys
    5 of 5 stars Reviewed 27 June 2015
    Great place and nice location to Mallory Square. Not too far of a walk to Blue Heaven which is a must. The pool was very nice and very clean. The Banana Key is a great condo that...
    5 of 5 stars Reviewed 16 January 2013
    We chose Banana Key just a few days before we actually got there due to a last minute vacation opportunity. I worked with Tim at Historic Hideways and couldn't have been happier...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    About this property
    Construido en la década de 1950, el complejo rezuma encanto de la época, sin retraso en el crecimiento de las comodidades. Las habitaciones cuentan con obras de arte cubano, TV de pantalla plana, mini-nevera, y hamacas. El hotel presta huéspedes coloridos sarongs para relajarse, y algunas... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    Totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Additional amenities include: sofabed, coffee maker, nearby beach, nearby bank, nearby internet cafe, ice maker, near beach, nearby medical... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 15 July 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for the...
    5 of 5 stars Reviewed 13 June 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    1 / 30
    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 July 2015
    The home was just lovely. Very clean, nicely furnished and quite comfortable. The pool was so refreshing and the courtyard was tropical with beautiful outdoor furniture. The...
    5 of 5 stars Reviewed 4 July 2015
    This house is in the perfect location with all of the need amenities! Just a wonderful place to stay and a great time! Enjoy ....you won't regret it!
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    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    Just like its name, Petunia is a happy place. Open the picket gate, walk down the short, bricked walk and open the original wood door with a grin from ear to ear. You’ve come home. This two-story, two-bedroom home with a beautifully updated, second-floor bath offers the kinds of privacy and... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 stars (53) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 January 2016
    Pamela's condo in Key West, FL was clean, nicely decorated and had an "at home feel". The balcony view of the pool is very beautiful and relaxing. This was our first family...
    5 of 5 stars Reviewed 29 December 2015
    Stayed with my wife and two teenage kids. The condo was very clean and well stock with every day essentials. The owner Pam is super to deal with and I would go back anytime...
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    1 / 30
    4.5 of 5 stars (58) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 4 weeks ago
    We enjoyed our stay and made use of the bikes and the pool. It is about a 10 minute drive to downtown and walking distance to a couple restaurants. We had a family of five and...
    5 of 5 stars Reviewed 4 July 2015
    Judy's condo, Tee by the Sea is really a great place to stay. The location is away from the crowds but close enough to be only a short drive or bike ride away. The condo has...
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    1 / 26
    5 of 5 stars (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Ocean Views
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    • Waterfront
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    • Pet-friendly
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    About this property
    ************************************************************************************************************************ ************************************************************************************************************************ Wake up to the sun rising over the sparkling Atlantic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 27 December 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
    5 of 5 stars Reviewed 4 November 2015
    We had such an amazing time in the Florida Keys. Staying at Atlantic Sunrise was icing on the cake. The condo is beautiful and the owners were so very kind! The notebook with...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    4 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 6 July 2015
    The renovations were great! The house is beautiful and updated. It is perfect for 2 couples. It is very private even though neighbors are close. I did manage to park a Dodge...
    3 of 5 stars Reviewed 25 November 2013
    We loved this house; and the pool. The photos are not totally accurate online in that the upholstery needs refurbishing on the furniture. And the pool looks larger in the photos...
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    1 / 17
    5 of 5 stars (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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    About this property
    Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. The original local artwork throughout... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 13 September 2015
    I arrived on a rainy, nasty day in Key West. It was pouring. Duval Street was flooding. The temperature was in the 50s. But I was in Key West, so it couldn't be all bad. It...
    5 of 5 stars Reviewed 10 December 2013
    We have been traveling to Key West 1-2 times a year for about 15 years and have stayed everywhere from the most economical to the high end resorts and will confidently say this...
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    1 / 16
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Live in the lap of luxury in this stunningly renovated Key West classic 'Eyebrow House.' An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed 16 June 2015
    My husband and I spent 3 months in this beautiful conch style eyebrow house. The pictures do not do it justice. The gorgeous yard with the pool, palms, mahogany trees and deck...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Hello,and welcome! This is cool and comfortable room with private bathroom, it comfortably fits two and it is located on a quiet street just 10 min away from Duval by car The apartment is very clean, complete renovation was done a month ago, everything is new and cool Room: Adorable bedroom,... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    New owners invite you to enjoy this vacation rental aptly named 'Seas the Day!' This newly updated 2 bedroom 1 bath first floor condo is located in the Shipyard section of the Truman Annex. If you are looking for a great location central to all that Key West has to offer, look no further! Park... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    The boat is big and very comfortable for my family (5) very luxurious to the smallest details, has a jacuzzi on the top and kajacs to navigate the beautiful sea. It was awesome...
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    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
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    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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    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 10 February 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed 31 October 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    1 / 14
    4 of 5 stars (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 28 May 2015
    Traveled with husband and teenage son. Plenty of room. Away from the really busy area of Key West. Clean. Close to the beach (brisk walk or bike ride). Did not use the pool...
    4 of 5 stars Reviewed 30 March 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
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    Holiday Rental Accommodation on Key West

    The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

    Water sports in Key West

    The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

    Popular attractions in Key West

    The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

    Restaurants and bars in Key West

    Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.