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Key West House Rentals

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    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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
    1 / 22
    4 of 5 bubbles (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This 4 bedroom 3 bath home is located in Key Haven (mile marker 5) Key West. Key Haven is a quiet neighborhood Great for boating, snorkeling, diving, fishing, biking, walking or just relaxing in the hammocks. Easy boating access to the Gulf and Atlantic (one canal from open water). Just 4 miles... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (38) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Key West, Florida Keys 33040
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    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 / 38
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    Studio, Sleeps 2 | Quick View
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    As the name suggests, the Garden House's 'Waterfall' rooms are tucked behind the tropical lagoon's waterfall... Just steps away from the breakfast and sitting area. Considering the location and price, you will not find a better deal in all of Key West This cozy bedroom shares a bathroom with... View all property information
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    Key West, Florida Keys 33040
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    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    This home requires a minimum stay of 28 nights :) Welcome to Cabana Chic! An amazingly gorgeous brand new monthly rental in the recently constructed Southernmost Cabana Resort. The home is nothing short of pure perfection. A completely turnkey, fully accommodating monthly vacation rental in Key... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ATLANTIC PARADISE -- Imagine the ocean only several yards from your balcony, in a secure gated complex, with all the amenities you could ask for -- pool, Jacuzzi, tennis courts, parking garage with personal parking space. That's what you'll find at Atlantic Paradise. Two spacious king bedrooms,... 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 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 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... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    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
    Location Information
    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 / 30
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Located at 729 Whitehead St, "Southern Palms" is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate... 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 / 25
    5 of 5 bubbles (51) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
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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 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 22
    4.5 of 5 bubbles (48) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire Key West rental property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (31) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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 condominium, constructed within an important piece of historic American architecture. Situated along the gateway waterfront to... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ISLAND WIND : Welcome to a tropical sun drenched oasis in the heart of Old Town Key West. This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award winning Windward Park, a gated and secure compound consisting of... View all property information
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    Key West, Florida Keys 33040
    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 / 32
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Due to licensing restrictions, this property has a minimum stay of 28 nights. Aqua Pearl Crest is a recently and completely remodeled 3 bed 3.5 bath home with a private pool, off-street parking & an outdoor shower. The open-concept kitchen is outfitted with stainless steel appliances and granite... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (56) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    LEEWARD ISLE KEY WEST RETREAT -- Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still... 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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    • Hot Tub
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    • x
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    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • ?
    About this property
    Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom townhome... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    About this property
    THE DOLPHIN HOUSE: Twice the comfort of and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is comprised of a bright and open main house and a lovely and bright guesthouse, with a pool and outdoor living space comfortably nestled in between.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    TROPICAL DREAMING -- A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while vacationing in Old Town. Only a short stroll over to Duval Street, where entertainment and activity abounds or 4 blocks to the Atlantic... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 45
    4.5 of 5 bubbles (2) Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • ?
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    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises when you walk inside. Villa Nouveau Key West vacation rental has an interesting story that attests to this truth. Once a prosaic 'shot-gun' style cottage, a modern redesign has... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
    Location Information
    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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    • Pet-friendly
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    • x
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (24) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • ?
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    DUVAL PENTHOUSE -- A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist,... View all property information
    Location Information
    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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    • x
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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
    Location Information
    Key West, Florida Keys 33040