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House Rentals and Condos in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 5
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 13, 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
    5 of 5 stars Reviewed July 25, 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped kitchen.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4 of 5 stars (55) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. 7 night minimum rental.Paradise is definitely found in this Non-Smoking,... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 27, 2014
    Our rental was clean, with plenty of supplies and towels. It was in a gated area and we always felt very safe. I loved sitting on the patio outside, enclosed by foliage so it...
    5 of 5 stars Reviewed September 2, 2013
    It was close to walk to Duval Street and short drive or walk if you like to Fort Zachary Taylor state park for swimming at the beach.
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    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    When I first toured this special Key West ~ Indies vacation house, I was struck by the refreshingly authentic blend of its multi-cultural exterior design and interior decor, and felt as if I could be standing in a villa in the British Virgin Islands (BVI). It's not surprising the home embodies this... View all property information
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    Key West, Florida Keys
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (12) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping, off street parking steps to your door, all in a private 3 bedroom 3 bathroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    This townhouse is everything it says it is. Sleeps and entertains 6 adults very well. 5 miles from downtown Key West, not walk able. Clean, well taken care of.
    5 of 5 stars Reviewed July 8, 2015
    Walked in the door and it was paradise. LOVED staying here, our concierge, Phil, was amazing, and the house was super comfortable and spacious. It looked just like a model home...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Part of Banana's Foster Guesthouse. This cute and colorful studio is perfect for anyone who is excited to explore Key West on a budget. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 21
    4.5 of 5 stars (37) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2014
    1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first floor...
    4 of 5 stars Reviewed September 9, 2013
    had a great time, I'll be back.
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    1 / 25
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named for President Harry Truman, is Old Town's premiere gated waterfront community. The manicured landscaping, verdant palms, and white picket... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed December 8, 2015
    We've stayed in this condo several times now. The location is great, just a hundred years from the World-famous Green Parrot bar and a few more steps to Duval St. However, it's...
    4 of 5 stars Reviewed May 17, 2015
    I loved staying at the Shipyard. The location was very quiet but was within walking distance of all the action at Key West. The only time we had to drive was to visit other...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... 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
    (Recently updated!) *** 1 Private, covered parking spot is included when you rent this particular vacation condo Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (35) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 16, 2015
    This 2 bed room condo is very clean, spacious and has what you need in the kitchen, extra linens, towels and beach towels for the pool. The 2 bedrooms are on the 2nd floor and...
    5 of 5 stars Reviewed October 30, 2014
    Nice two bedroom condo, well furnished, great location. Would definitely stay here again. Becky and her staff at the rental company were a pleasure to work with.
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    The Condos are tied together in a lushly landscaped garden setting with a spa pool in the rear. Booking all 4 condos gives you a great alternative to booking a single house as you are offered privacy and closeness at the same time. Call to book your Island Paradise while there is still time! Palm... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 stars (31) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week ago
    This is the second time my husband and I have stayed at one if the units in the Villas. The location is fantastic - walk to the action on Duval or the beach. And the property...
    5 of 5 stars Reviewed June 28, 2015
    We had a large group in 5 of the units for my daughter's wedding and absolutely loved our stay. The townhouses were equipped with everything we could possibly need and very clean...
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    1 / 10
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 16, 2015
    We had a great time staying here because we could walk/bike to everything! There is a bike/electric car rental place across the street and they are so nice! (Tropical Rentals...
    5 of 5 stars Reviewed September 23, 2014
    This place was great for my spouse & me and grown daughter & friend to stay during our visit to Key West this summer. the two bedrooms are big, comfortable and have their own...
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    1 / 24
    5 of 5 stars (13) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed 1 week ago
    We had a great week at Kemp house. Just far enough away from the noise and business of Key West revelry, and yet just a short walk or bike ride to everywhere. Bike rental right...
    5 of 5 stars Reviewed August 11, 2015
    Great property! The house had everything ANYONE would ever need. Pool was a tropical paradise. We had three couples and one 7 month baby and we had ample space. Management...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
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    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 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 28, 2015
    We very much enjoyed this condo. It is beautifully decorated and there is a high priority for safety. Each condo has a private elevator that can only be entered with a specific...
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    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people come to Key West to stay for a month or more! Live the island lifestyle outside enjoying the front porch, the second floor balcony, and the side lounge area with cocktail pool.... View all property information
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    Key West, Florida Keys
    1 / 28
    4.5 of 5 stars (24) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 17, 2015
    SEA BREEZE was great we were a block away from the 90miles to Cuba attraction. it was really close to little beach "south beach" it was very clean and had 1 parking spot just...
    4 of 5 stars Reviewed February 7, 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now... View all property information
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 28, 2014
    We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location! Across...
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 15, 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 June 13, 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 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a classic four bedroom, four bath 'eyebrow' style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has a large... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a recently renovated private home with three bedrooms and two baths located in a quiet, Old Town, Key West neighborhood only 10 minutes to Duval Street and only 5-10 minutes to Smathers Beach. 3... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    5 of 5 stars (10) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    A Key West Gem! Fine dining abounds here with great restaurants such as Square One, Origami Sushi Bar and Panini/Panini, which offers free wi-fi). In the “must have” location of historic, old town Key West, it is a second story home-away-from-home, just steps from the sights, sounds and... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 24, 2014
    Had a great time staying in this condo with 4 of my besties! We enjoyed having plenty of space...upstairs and downstairs, 2.5 baths...great for 5 women! The location of the...
    5 of 5 stars Reviewed April 16, 2014
    This is a fantastic complex and is managed/owned by Rick who will go out of his way to make you happy. He picked us from the airport, fishing and back in his Escalade at no...
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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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 29, 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 May 28, 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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    1 / 29
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Beautiful second floor studio for two on the second floor of the historic Sailmaker's House. - Incredible location in Historic Old Town! This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. The open floor plan maximizes the... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 29, 2015
    Really loved my time spent here. It was clean and the pictures were accurate. The studio is great for the solo traveler looking to be super close to the seaport and restaurants...
    5 of 5 stars Reviewed February 10, 2015
    I've been to Key West many times and know the city as well as my home town. First, the most important thing is LOCATION. You want to be within walking or biking of all the...
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    1 / 22
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed March 4, 2015
    Block and a half to Duval. You can walk to Southern Most Pt, Hemingway's house, Truman White House, Boat Dock, Aquarium, Ft Taylor & all restaurants. Of the 8 nights we were...
    3 of 5 stars Reviewed February 3, 2015
    Nice little unit, but would have preferred being downstairs. Had a slight musty smell when we first arrived, but after some cleaning it was much better. The unit is nicely...
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    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. The front porch is perfect for people watching and chatting with locals passing by. Once you step into the open... View all property information
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    Key West, Florida Keys
    1 / 24
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Sauna
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    • Hot Tub
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    About this property
    Beautifully remodeled, 1374 sq. ft., 2 bedrooms (both are King Beds) 2 Bath condo located on the beach in a resort complex -(SLEEPS 6). Gorgeously landscaped & located RIGHT NEXT TO SMATHERS BEACH, the largest beach in Key West! AMENTIES INCLUDE: Private 40' Balcony, Master suite, Resort... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 8, 2015
    This is a nice complex and the unit was very nice. If you like a quiet area of Key West this is it. It is really to far from the old town area to walk and parking in Key West is...
    5 of 5 stars Reviewed January 6, 2014
    I traveled with my wife and 4 teenagers. The best part about this condo was its location...It was a short walk to Smather's Beach in one direction, and 1 mile from Duval St. in...
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    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
    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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    The Double Delight is a large accommodation consisting of two double beds, a vanity and separate private bath. The Double Delight provides the perfect setup for couples, friends or family members traveling together during their Key West vacation. If you would prefer two bedrooms with a shared... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (16) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed June 30, 2015
    My family stayed here for a week. The accommodations were excellent. Everything we needed was provided. Great location! Would recommend this to everyone.
    5 of 5 stars Reviewed April 8, 2014
    We rented this 4 bedroom 3 bath house for vacation with our adult children, 6 month old grandson and 87 year old father. It was perfect! One bedroom downstairs for Grandpa, a...
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    1 / 22
    4.5 of 5 stars (72) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed September 14, 2015
    Rose Cottage was a wonderful place to stay! We visited during the off season for our anniversary/birthday, and enjoyed the privacy and peacefulness of the cottage surroundings...
    5 of 5 stars Reviewed September 13, 2015
    Hard to believe that this quiet little cottage is just a half block off of Duval on an alley that runs between Fat Tuesdays and Hard Rock Cafe. We've stayed here many times and...
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    1 / 19
    4.5 of 5 stars (8) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the  fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 2, 2015
    We stayed at Penthouse on Duval for a week, renting the entire unit (4 Bedrooms and 4 1/2 baths) and it was absolutely as described including the pictures. It was large...
    5 of 5 stars Reviewed June 30, 2015
    This place was absolutely perfect. We came down and stayed with 10 of our closest friends and family for my mother-in-laws 70th birthday party. The place was beautiful and the...
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    1 / 20
    5 of 5 stars (25) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 8, 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 stars Reviewed August 19, 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    1 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each suite is furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 22, 2015
    This condo is stunning and very clean. We were close to all the action to Duval, which was fantastic. We walked all day long and left the car rental parked unless we needed to...
    5 of 5 stars Reviewed September 11, 2015
    The suite is clean, comfortable, spacious and perfectly located in the middle of Old Town Key West close to everything. The rental agency was super helpful (we were 24 hours late...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View Florida Keys condo for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. Located on the Atlantic Ocean... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Lovely studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to it's fullest in this highly desired walking... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 30, 2015
    Nice neighborhood, close to water. Attentive property concierge. Just a few blocks from water and many great bar and grills. Cozy studio.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Bluewater is a classic porch-on-porch Key West home with all the amenities to make your vacation ideal. Located in the prestigious Sanctuary of the Key West Golf Club, the house has two bedrooms each with its own private bath. The house sleeps 4 adults and two children or smaller adults. It... View all property information
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    Key West, Florida Keys 33040
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Nestled in one of Key West's original gated 'mini-compounds,' the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    2 of 5 stars (1) Poor
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do.... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 30, 2015
    We stayed in this house in early December for my husbands 40th birthday and there aren't enough good things to say about it. The house is extremely spacious and private and even...
    5 of 5 stars Reviewed April 12, 2012
    Wonderful place. As nice as photos in ads. Pool has sun all day, am and pm! Plenty of bathroom space. Lovely kitchen. We managed a week without a car. Not too far to walk to all...
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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.