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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking February dates now. Secure your holiday home today, and have the perfect trip.
    1 / 25
    4 of 5 bubbles (1) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 18
    5 of 5 bubbles (2) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 33
    5 of 5 bubbles (20) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 22
    4 of 5 bubbles (1) Very good
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    3.5 of 5 bubbles (9) Average
    Key West
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    "In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    MINIMUM STAY: 1 MONTH Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen counter. There is a large... View all property information
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    Key Largo, Florida Keys 33037
    1 / 14
    4.5 of 5 bubbles (7) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Central Air Conditioning. This apartment is in the same building that has our office adjacent to it. This is a beautiful apartment. TV with 75 channels, linens, central air, brand new bathroom with all new fixtures and brand new kitchen. Our price has no hidden additions-just sales tax. The... View all property information
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    Key Largo, Florida Keys 33037
    1 / 31
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Vacation Rental License No VR-001 Mile Marker 86 We are a licensed private pool vacation home/ deep sailboat canal and licensed to rent by the WEEK. Email me for the application at VenetianTropics ( we are not allowed to insert our email address, but you can find me on the web or simply click on... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 15
    5 of 5 bubbles (2) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Minimum Rental: 7 Nights SATURDAY to SATURDAY Calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal fishing is at your... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 9
    4.5 of 5 bubbles (6) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 31
    4 of 5 bubbles (4) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value. This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,... View all property information
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    Key West, Florida Keys
    1 / 24
    5 of 5 bubbles (1) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Plan your next Shore Leave at this gorgeous waterfront Key Largo home on Largo Sound, Oceanside near Mile Marker 103! Beautifully furnished and updated, with living room, kitchen and half-bath at ground level & 3 bedrooms & 2 bathrooms upstairs. Master bedroom has a Queen bed. Guest bedroom #1 has... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    5 of 5 bubbles (4) Excellent
    Key West
    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
    1 / 23
    5 of 5 bubbles (1) Excellent
    Long Key
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    MINIMUM STAY 1 MONTH - You and your entire family will love this serene, quaint part of paradise, in this ultra-charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has plenty of room for your whole family to... View all property information
    Location Information
    Long Key, Florida Keys 33036
    1 / 30
    5 of 5 bubbles (3) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights </b> Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4 of 5 bubbles (1) Very good
    Key West
    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 / 28
    Key West
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (5) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This truly tropical retreat Keys’ home has an open floor plan, vaulted ceilings, and modern open kitchen. Master Bedroom has king sized bed, full bathroom with shower, granite sink, walk in closet, glass block windows. Second Bedroom has queen sized bed, closet, and adjoining bathroom with... View all property information
    Location Information
    Marathon, Florida Keys 33417
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    1 / 27
    5 of 5 bubbles (4) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    <b> Minimum Rental: 7 Nights </b> Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit... View all property information
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    Islamorada, Florida Keys 33036
    1 / 9
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located at mile marker 100 in beautiful Key Largo, Florida. The unit has 1600 sq. ft. of living space and 400 sq.ft. of wrap around porch. One master bedroom with king bed and large private bath. Guest bedroom has 2 double beds. Large Kitchen dining and living area overlooking the grounds and dock.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 17
    Marathon Shores
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Open Water Elegance & Charm describe this spacious 3 bedroom, 2.5 bath private pool home offering spectacular open water views. Large patio and heated pool area perfect for entertaining. You will find deep water dockage and Ocean views from almost everywhere in the home. Located in a superb... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 16
    4 of 5 bubbles (1) Very good
    Marathon
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** "Margarita on the Gulf" is a spacious 5 bedroom, 4 bath home located on the Gulf of Mexico. Enjoy endless gulf views as you relax at this private tropical setting with large pool, hot tub, and sun deck with BBQ.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 45
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    This is an Efficiency 1 bedroom apartment located in Captain Jax's RV Park which has a Marina, Docks, Beach and magnificent sunsets. Tile Floors, air conditioned, clean. Cook top, Microwave-Refrigerator. Water View. Park outside your door-Laundry. Couch can accommodate one guest to sleep in... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 20
    Key Colony Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    One of Key Colony's finest: Exquisite and spacious 4 bedroom, 2 bathroom, private pool home in the desirable Key Colony Beach neighborhood just minutes to beaches, restaurants, golf and tennis. Offering large living room, dining area, sitting room and lots of outdoor living space including outdoor... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33037
    1 / 27
    4 of 5 bubbles (1) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM 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... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (6) Very good
    Marathon
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This 4 bedroom, 4 bath property is great for family vacations. Less than 30% of all rentals in Marathon are 4 bedroom or larger. HOW MANY PEOPLE CAN SLEEP AT THIS 4 BEDROOM? Our rental license allows up to 10 people to stay overnight. Three of the... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 23
    5 of 5 bubbles (2) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the moment you... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 12
    4.5 of 5 bubbles (7) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Bayside condo in a 10 unit complex overlooking dock and canal. This unit is located in the center of Key Largo with access to shopping and great restaurants. Perfect for the avid diver or fisherman as there is a dive shop and bait shop located in the complex. This is a 1 bedroom with a King bed... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 7
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    A large, lovely, spacious and comfortable cottage with plenty of room for the whole family. Centrally located, across from the pool with a back door leading to the beach. Sleeping accommodations include a king bed in the master bedroom, two queen beds in the second bedroom and a queen sleeper sofa... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 10
    5 of 5 bubbles (41) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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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. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    Key West
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    5 of 5 bubbles (1) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located on a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    4 of 5 bubbles (29) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    PAPAYA PLACE pops with color! This great 2 bedroom 2 bath waterfront Key West rental condo at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    Islamorada
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 13
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
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    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 42
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Bright and airy PET FREE,SMOKE FREE 1 bedroom, 1 bath home with large lanai [705 sq. ft.] at mm 101.5 on deep water swimming canal in gated Key Largo Kampground. The MINIMUM STAY IS A WEEK, [see rates section listed above] plus 12.5% tax] The preferred stay is a month...especially in January... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 15
    4.5 of 5 bubbles (5) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** Bird of Paradise Condo is a tropical three bedroom condo directly on the ocean - BEACH FRONT! Enjoy the feel of smooth, white sand on a private beach, swim in the large heated pool, or play on the tennis court. This... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 24
    4 of 5 bubbles (45) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    OSPREY - This bright and colorful studio Key West rental cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ideal location just three blocks from... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (51) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
    • x
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    • 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
    Location Information
    Key West, Florida Keys
    1 / 23
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Minimum Stay 1 Month. 'Beba's Reef House' will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a charming 2... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 6
    5 of 5 bubbles (1) Excellent
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    Our 'House Boats' are a boat lovers dream with all the comforts of home, including full bathroom (head) with stand up full size shower, full kitchen (galley) with all amenities, living area with sofa, dining table and TV. It has a generous outdoor patio with seating for two along with a complete... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 26
    3 of 5 bubbles (1) Average
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    KEY WEST FOUND - A striking 2 bedroom, 2.5 bath townhome 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 floor features open and airy... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 7
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    'Welcome Aboard' as we say here at Mangrove Marina, located in the northern end of Islamorada in Tavernier at Mile Marker 91.7 on the Bay side in a protected tranquil oasis cove of the beautiful Florida Keys. Our 'House Boats' are a boat lovers dream with all the comforts of home, including a full... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 15
    4 of 5 bubbles (22) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    • ?
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    • x
    About this property
    In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    Key West
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Shared Outdoor Pool...
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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
    1 / 24
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
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    MINIMUM STAY: 28 DAYS NEW LISTING - Available this winter! But Hurry… this home promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as... View all property information
    Location Information
    Islamorada, Florida Keys