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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 / 24
    5 of 5 stars (12) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 27
    4.5 of 5 stars (31) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 20
    3 of 5 stars (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room Seven is a magnificent room on the third floor with unique and fun architecture. It is painted in a tropical green tone that is soothing and a lovely contrast to the tropical greens of Key West. The private bath will make this room an exceptionally comfortable home away from home. This room... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Both bathrooms completely renovated as of September, 2015*** Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 15, 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    5 of 5 stars Reviewed July 29, 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    1 / 8
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 stars Reviewed May 14, 2014
    The condo was very comfortable and in a great location in being able to walk about anywhere. The only item from the 5th star is the matteresses could be replaced.
    5 of 5 stars Reviewed November 28, 2011
    This unit was in the perfect location to experience Duval Street and Mallory Square. Close walking distance to everything and yet just far enough away so you do not hear the...
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    6 Bedrooms, 6 Bathrooms, Sleeps 24 | Quick View
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    About this property
    Southernmost Sanctuary Suites are comprised of the following homes Egret Suite, Heron Suite, Ibis Suite, Osprey Suite, Pelican Suite, Seagull Suite which can all be booked individually. Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 5, 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
    5 of 5 stars Reviewed January 27, 2015
    Loved our stay at toon hall. Awesome home away from home. Had all amenities we needed and location was great. Property was private and secure. Staff was responsive to...
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    1 / 7
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    This condo is absolutely amazing!! The pictures on the web site are exactly how it looks when you walk in. The bedrooms are large with a bath off each. A large walk in closet...
    5 of 5 stars Reviewed November 19, 2015
    Our room exceeded our expectations in every way. All of the appliances were brand new, the paint was fresh and every part of our apartment was spotlessly clean. I can't wait to...
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    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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    1 / 32
    4.5 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 19, 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    4 of 5 stars Reviewed November 11, 2014
    Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described as... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 4, 2010
    The best place to have a taste of old Key West. Not at all like anything you would rent anywhere else in the country!It was walking distance to everything in Old Town and the...
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    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Ahoy! PirateHead Cove, your affordable vacation dream-come-true is now taking bookings for 2016! Max occupancy: 2 couples or 1 couple with up to 3 children under 12. The calendar on this site shows availability. We do not take partial weeks or bookings of less than 7 nights unless it is between... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $541
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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 / 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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    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
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    Key West, Florida Keys 33040
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling,... View all property information
    Location Information
    Key West, Florida Keys 33040
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
    Location Information
    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as 'Curry's Rooms' in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
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    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This cute and colorful studio is perfect for anyone who is excited to explore Key West. You are just around the corner from all Duval Street has to offer. Restaurants, bars, shops, live music.. it's all just steps away. Be sure to catch the sunset at Mallory Square and a bite to eat on the harbor.... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 22
    4 of 5 stars (38) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 26, 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
    5 of 5 stars Reviewed November 4, 2014
    My wife and I stayed at the Sunset Suite - Nightly which is managed by Key West Vacation Rentals. This was our first trip to Key West as we went for the Meeting of the Minds. We...
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    1 / 31
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 21, 2015
    My 1st visit to Key West was in 1971 when it was a small, end of the road, sleepy beach town with old homes & history. Things have changed & it has grown tremendously. One thing...
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    1 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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 September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    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 / 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
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed June 27, 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 January 16, 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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    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 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Recently updated with new furnishings, premium linens, wifi and flat screen TV Feeling the need for an antidote to mainland stress? Or maybe you’ve finally decided to write that novel, paint that picture or write that piece of music that’s been tickling your brain? Solaris Cottage, located on... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 5, 2015
    The Solaris cottage was down a quaint little lane that was smack dab in the middle of the historic district of Key West. We were in short biking distance of every place we wanted...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (48) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    One block from Center St, Hemingway's View is a 3 bedroom, 2 bath charming turn-of-the-century Conch cottage. Each of the 3 bedrooms are air-conditioned. Both bathrooms have marble floors, large closets, hairdryers, and tubs with showers. The rear bath has a marble topped vanity with double sinks... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 1 week ago
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while the...
    3 of 5 stars Reviewed December 2, 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    1 / 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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    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Island living is made easy in this tropical one bedroom, 2-story Key West cottage. A classic-contemporary Key West style, this attractive rental home is designed with a graceful spiral stair case that connects the 1st and 2nd floors and a romantic gingerbread Juliet-style 2nd floor balcony... View all property information
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    Key West, Florida Keys
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $188
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    About this property
    Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $159
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    • Porch
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    About this property
    CALL AND ASK ABOUT OUR WEEKLY SPECIAL WITH 1 NIGHT FREE! You will love staying in this great Key West historic old town location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm,friendly and diverse group. Here you will absorb the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 5, 2015
    Great deal!!! We came down end of July beginning of August for a friends wedding. While it is extraordinarily hot this time of year in Key West, we made the best of it! Great...
    5 of 5 stars Reviewed May 7, 2015
    Location was great, bike rental shop on the corner, but even walking was not far. Marilyn was a breeze to deal with and the apartment was exactly as described. No issues at all...
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    1 / 29
    3 of 5 stars (5) Average
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 14, 2014
    Coral Cove was a great place to stay for 2 people. We only stayed for one night, which was just enough. It was a little cramped, but was a safe and comfortable place to sleep. It...
    4 of 5 stars Reviewed December 4, 2013
    Good service, clean and well-maintained. Accommodates dogs but with 2 people, a border collie and a 12 lbs. poodle, the room is entirely too small. The mattress in our room needs...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    4 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $550
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    • Air Conditioning
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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 July 6, 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 November 25, 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 / 26
    4.5 of 5 stars (20) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $388
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 11, 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    5 of 5 stars Reviewed October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Room 2's pale shade of coral will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private bathroom... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4.5 of 5 stars (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $240
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed September 19, 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
    5 of 5 stars Reviewed May 11, 2013
    My new husband and I selected ann Street Tranquility for our honeymoon and we could not have been more happy with our choice!Everything about ann Street Tranquility was amazing...
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    1 / 23
    4 of 5 stars (32) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $300
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    • Balcony
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    • Pet-friendly
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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
    4 of 5 stars Reviewed October 16, 2015
    This condo was a bit dated and could a little TLC, but overall worked great. The location was nice on the water and was not too far from downtown. Everything worked really nice...
    4 of 5 stars Reviewed September 4, 2013
    Stayed at Pelican Landing in a group of 8. The interiors were all nice and comfortable with clean bathrooms and kitchen. Beds were comfortable and sheets were clean, sofabed was...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $2,800
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    • ?
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    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will fall... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    $725
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    • Pet-friendly
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    • x
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    About this property
    28 Night Minimum Stay Requirement - The Treetop Apt at The Sailmaker's House This second floor one bedroom apartment has one of the most desireable walking locations in Historic Old Town. Located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. There is a 28 night... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $235
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    • Wi-Fi
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    • Ocean Views
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    • x
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    About this property
    You have the use of one of four private cabins each with its own marine style bathroom and queen like bed for $235.. Three cabins available for six or less guest for $695. Captain Charles and wife Deborah use one cabin. You may choose our sunset sail for $50 per person that includes snacks and non... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of the Nightly Group PALM GARDENS Flamingo Hideaway is a spacious unit. Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details. The original Dade County pine walls have been saved to create that unique... View all property information
    Location Information
    Key West, Florida Keys
    5 of 5 stars Reviewed July 31, 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
    3 of 5 stars Reviewed April 3, 2014
    The home we stayed in (905 White street- Flamingo) was wonderful. It was very clean, well kept and a great getaway from the business of Duval Street. We rented bikes so we only...
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    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $225
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    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
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    $3,500
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    About this property
    A hidden jewel in the old town of Key West. A private garden, with pool, and fountain, covered porch, and space to sun. Comfortable bedrooms, with a loft to sleep 2. fully equipped kitchen, air-conditioning internet, tv, cable. Bes quiet neighborhood. This home rents by the month and is occupied a... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 stars (20) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    $208
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    • ?
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    • x
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    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed September 9, 2015
    Harrison's Hideaway was the perfect fit for our 10th Anniversary getaway. The cottage was very clean and remodeled with newer amenities. I would suggest against having a car on...
    5 of 5 stars Reviewed September 2, 2014
    Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
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    1 / 34
    4.5 of 5 stars (15) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $850
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    • Pet-friendly
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    • Child-friendly
    • x
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    • Elder access
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    About this property
    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 2, 2013
    After reading great reviews about the Villa Tropicale, we rented this property for six nights last month. We were traveling with a group of eight and wanted a large home where we...
    5 of 5 stars Reviewed January 27, 2013
    This was not our first stay at Villa Tropicale and we certainly intend to come back. When we first opened the gate of the property a few years ago, we were delighted to discover...
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    1 / 28
    5 of 5 stars (3) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    **Recently Renovated!! Part of Southern Palms Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly 'green unit'. Your roommate, or in this case, 'suite mate' is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 12, 2014
    We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait to...
    5 of 5 stars Reviewed July 29, 2014
    From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport pick-ups...
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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.