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Key West House Rentals

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    Studio, Sleeps 2 | Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    In one of the most desirable locations in Key West, you will find the exquisite 2CoolFish. Located in Truman Annex. Just walking into this pristine home will take your breath away. Featuring two bedrooms and one and a half bathrooms, this home is perfect for a family or small group of friends... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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    Key West, Florida Keys 33040
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Caribbean Dreams is an inviting space, decorated in rich wood and cane furnishings, perfect for your Key West vacation! Just a few steps up from the garden entry path, 'Caribbean Dreams' offers a calm and cozy atmosphere. Enjoy the ultra comfy queen sized bed, free wifi, and daily housekeeping.... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical... View all property information
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    Key West, Florida Keys 33040
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Room 1 is considered by many to be one of the nicest rooms the Curry House has to offer. Newly painted, "Barely Teal", this room highlights a four-poster bed. The recently remodelled private bathroom is spacious and includes a stunning tiled, marble shower. A semi-private veranda overlooks the... View all property information
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    Key West, Florida Keys 33040
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Part of Banana's Foster Guest House This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with... View all property information
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    Key West, Florida Keys 33040
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    1 / 25
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    An excellent value, Room 3 is delightful and comfortable. This room is unique in the Curry House in that it is the only room with French doors that open up onto the second-floor porch. Room 3 shares a bathroom with Room 4. The bathroom is exclusive to these two rooms and has an island charm all... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    Key West, Florida Keys 33040
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+   Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys style. No detail has been over - looked, No stone un-turned, every vantage... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ISLAND WIND: 2 bedroom, 2 bath Bahamian-style townhome, with tin roof and white spindled decks. Snuggle into an oh-so-comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs with 2 twin beds; bathroom ensuite with entrance from the kitchen. Open floor... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    4 of 5 bubbles (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 25
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the... View all property information
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    Key West, Florida Keys
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    1 / 23
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests... View all property information
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    Key West, Florida Keys 33040
    1 / 11
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 35
    9 Bedrooms, 9 Bathrooms, Sleeps 18 | Quick View
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    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 commercial kitchen serves breakfast each morning by the pool. Eight of the rooms have doors onto verandas, four... View all property information
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    Key West, Florida Keys 33040
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    6 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Havana Oasis is comprised of two of our most popular homes! Island Oasis 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.... View all property information
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    Key West, Florida Keys 33040
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    5 of 5 bubbles (24) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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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
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    Key West, Florida Keys 33040
    1 / 35
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks to the Historic Seaport District or the Art Gallery District on White... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental View all property information
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    Key West, Florida Keys 33040
    1 / 27
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (50) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 bubbles (7) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    At last, a magnificent 3-bedroom home in the middle of Old Town with room for all. This home is a BIG secret but not for long! Lushly landscaped grounds with meandering brick walkways leading to the main house, pool and guest cottage. New owners with new furnishings and linens, breathing new life... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate... View all property information
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    Key West, Florida Keys 33040
    1 / 47
    5 of 5 bubbles (1) Excellent
    12 Bedrooms, 9 Bathrooms, Sleeps 36 | Quick View
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    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family. COTTAGE @ TROPICAL VILLAGE:... View all property information
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    Key West, Florida Keys 33040
    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
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Air Conditioning
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Welcome to Paradise a lovely place to call home for a month* or more in Key West! Just minutes from the excitement of Duval Street, the NY caliber plays at The Waterfront Theatre, exceptional fishing and swimming in the turquoise waters … Yet nestled in the serene environment of the KW Golf Club... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 56
    4 of 5 bubbles (1) Very good
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Garden
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    • x
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    • x
    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
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    Key West, Florida Keys 33040
    1 / 47
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 20 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation. Old Town Garden Villas is comprised of the following... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (51) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    January Dates now OPEN! This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    About this property
    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    Beautifully decorated with abstract art throughout, this 2 bed 2 bath monthly rental is the perfect "get away" spot for individuals looking to fully immerse themselves in Key West culture. This house is located in on Royal St. in Old Town Key West. It is located only a few blocks from Duval St and... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • ?
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    • ?
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This well-manicured, "home away from home" is two stories of wonderful Key West! It has three bedrooms, three gorgeous bathrooms and has a colorful, comfortable style. The traditional white picket fence greets you when you arrive. Though, it's only a glimpse of the wonder that awaits. Beyond... View all property information
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    Key West, Florida Keys 33040
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Secure Parking
    • Children's Pool
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    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spacious residential-style 2-bedroom/2-bath villa features private balcony, Master suite with king bed and connecting master bathroom and spa tub; Guest queen bedroom & guest bathroom; Fully equipped kitchen with separate dining ares; Living room with sofa bed; TV/DVD Blu-Ray. Exclusive amenities... View all property information
    Location Information
    Key West, Florida Keys 33040