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Key West Vacation Rentals

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... 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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    1800 Atlantic Condominiums Unit C439 Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, two bath penthouse condo has just been upgraded including a large, well equipped, open-design kitchen with all new appliances, bamboo cabinets, granite counter tops and an elegant... View all property information
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    Key West, Florida Keys 33040
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    4 of 5 bubbles (3) Very good
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Florida Keys area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customized vacation tailored to you... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    5% OFF already discounted prices for April - July! Please call our office for details. En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots.... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is... View all property information
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    Key West, Florida Keys 33040
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    1 / 12
    3 of 5 bubbles (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Newton's Nest is a quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls, eclectic Key West furnishings and details along with... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a... 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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    CORAL CASITA 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 located in the gated... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 bubbles (4) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    10% OFF already discounted prices for Open dates in April & May! Please call our office for details. Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed,... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    28 Night Minimum - Monthly Rentals Only Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. The front porch is perfect for people watching and chatting with locals... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's tranquil tree lined streets. Centrally located on the island, yet far enough away from the hustle bustle of Duval, this is truly a wonderful locale... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,... View all property information
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    Key West, Florida Keys 33040
    1 / 54
    3.5 of 5 bubbles (2) Average
    Studio, 11 Bathrooms, Sleeps 24 | Quick View
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    The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    Studio, 4 Bathrooms, Sleeps 12 | Quick View
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    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated... View all property information
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    Key West, Florida Keys 33040
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    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Cute 2 bed 1.5 bath house located in the Key West Golf Club with fenced in yard. New Furnishings and Appliances. Great location, steps to golf clubhouse and visitor parking, 2 miles from airport, very close to shopping, and 4 miles from Duval. Private setting with no neighbors to back, fenced... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (64) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles... View all property information
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    Key West, Florida Keys 33040
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (18) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... 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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    ***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 / 25
    4.5 of 5 bubbles (51) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... 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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    This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through breeze and expansive views of the tropical courtyard. As assigned private parking space will convey with your rental. You can feel secure in our fortress or a property. Key West is... 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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    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around... 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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    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman... View all property information
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    Key West, Florida Keys 33040
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... 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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    About this property
    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 bubbles (15) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The unit offers a well- equipped kitchen, a living room that opens to a... View all property information
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    Key West, Florida Keys 33040
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    4 of 5 bubbles (6) Very good
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract... View all property information
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    Key West, Florida Keys 33040
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    This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana, and it's available to rent together from May 2016... View all property information
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    Key West, Florida Keys 33040
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    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
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    4 of 5 bubbles (26) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    4 of 5 bubbles (4) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back to Key West. As... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    28 Night Minimum - Monthly Rentals Only Just like its name, Petunia is a happy place. Open the picket gate, walk down the short, bricked walk and open the original wood door with a grin from ear to ear. You’ve come home. This two-story, two-bedroom home with a beautifully updated, second-floor... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Internet Access
    • Parking
    • Washer
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 9
    4.5 of 5 bubbles (6) Very good
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Terrace
    • Hot Tub
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    28 Night Minimum - Monthly Rentals Only History buffs love to immerse themselves in the centuries old legends of Key West – and if they’re lucky, they’ll find room in Smuggler’s Den to celebrate the tall tales of smugglers, pirates and colorful outlaws whose stories are part of the fabric of the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Yard
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which makes it a perfect spot to vacation as it is a quick safe walk to everything Key West has... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Parking
    • Air Conditioning
    • Grill
    • Satellite TV
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Bahama Village this 5 Bedroom, 2 Bathroom house sits in a divine location. Just one block from the Historic Duval Street, and minutes from many other attractions. Fenced in yard provides a private, secluded space to relax on your island vacation. This large island home boasts Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (39) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 38
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • Sauna
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the length of the unit. The unit is tiled throughout with a full size fully equipped eat in Kitchen. There is also a full size washer dryer for your convenience. Both bedrooms and the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Hot Tub
    • Washer
    • Sauna
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersports activities available. The property itself features assigned secure parking spaces, 3 lighted tennis courts, one of which is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 43
    Studio, 6 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a... View all property information
    Location Information
    Key West, Florida Keys 33040
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