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Vacation Rentals in Florida Keys, FL

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    1 / 6
    3 of 5 bubbles (1) Average
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 34
    4.5 of 5 bubbles (2) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 33
    Key West
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 29
    4.5 of 5 bubbles (12) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    1 / 20
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • x
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    • x
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything... View all property information
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    Islamorada, Florida Keys 33070
    1 / 27
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Hibiscus is located just steps from our heated lagoon pool and adjacent to the Bougainvillea Room. Both Hibiscus and Bouganvillea share a large, semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common... View all property information
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    Key West, Florida Keys 33040
    1 / 45
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Sauna
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    • x
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    About this property
    Stay at a Luxury Townhome. Recently remodeled... Everything is new! Beautiful kitchen fully equipped , TV in each room, three patios, located just off the heated pool (literally 20 steps away from the pool) plus a kiddy, parking is right outside the front door. Beautiful sunsets from the balcony... View all property information
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    Key Largo, Florida Keys 33037
    1 / 33
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (28) Very good
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    5 of 5 bubbles (1) Excellent
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Down stairs apartment with King size bed and Queen Sofa bed. Boat dockage available with this unit. Very nice place. If your looking for a party pad this is NOT it. Very quiet neighborhood. Outside bar and tables available to use. Also a gas grill is available. If you bring a boat a 32 ft is... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 31
    4 of 5 bubbles (24) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • ?
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    • x
    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    5 of 5 bubbles (3) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • x
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    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    3 of 5 bubbles (1) Average
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Terrace
    • Air Conditioning
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    • Balcony
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    • Washer
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
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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 / 20
    3 of 5 bubbles (1) Average
    Key West
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
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    • DVD Player
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    4 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' If you are looking for gold sinks, with gold fixtures, this is not the place for you! We are a "rustic" retreat where the relaxed life of yesteryear can be enjoyed. Our specialty is providing you and your family with the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 18
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    About this property
    Welcome to the Salvador Dali Suite, located in Old Town Key West just a few blocks from Duval St! Efficiency and affordability at its finest! The Salvador Dali Suite has everything you need to fulfill your Key West Vacation needs - a super comfy, full-sized bed, a kitchenette complete with a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 of 5 bubbles (1) Very good
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Hot Tub
    • Private Garden
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    • Pet-friendly
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    • x
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    • x
    About this property
    Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40' flat screen TV, and the guest room is equipped with a very sturdy wood bunk bed with a... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 38
    4.5 of 5 bubbles (4) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    • ?
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    • x
    About this property
    Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly "green unit". Your roommate, or in this case, "suite mate" is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio apartment comes complete with a... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    5 of 5 bubbles (10) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,... View all property information
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    Key West, Florida Keys 33040
    1 / 8
    5 of 5 bubbles (1) Excellent
    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
    About this property
    Tiki Beach is a 3 bedroom, 2 bath bungalow located on the Gulf side of the island of Big Pine Key. Over an acre and a half with 150 ft of open water frontage and a private pool, hot tub and lighted dock that allows for a boat with up to a 3 foot draft at average tide levels. Water supply on dock... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 20
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    ocean front paradise with 95 feet of ocean frontage. Exotic natural serene setting with easy ocean swimming and access. Customer responses equate it with a resort atmosphere and very unique dense fauna sheltering trees, flowers,and visits frequently by humming birds, tree frogs and the like.... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 25
    4 of 5 bubbles (1) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Decorated in a cozy island style, the Gecko Grotto is located adjacent to our heated lagoon-style pool, and just steps away from breakfast! Throw your suitcase on the luggage rack and start to relax! The theme is truly Key West and little island touches are sprinkled throughout the decor. The... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • 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 / 30
    5 of 5 bubbles (2) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Smoking allowed
    • 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
    3 of 5 bubbles (1) Average
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    It’s just what you need. Minutes from Miami, yet seemingly a world away. The vacation you deserve is waiting for you in this elegantly well-appointed ocean-side condominium. What's more we understand what you are looking for in a vacation rental. Enjoy the fresh feeling you experience when you... View all property information
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    Key Largo, Florida Keys 33037
    1 / 44
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
    About this property
    Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with a brand new private 16' x 32' in ground cement swimming pool with splash deck. This two bedroom , two bath home is newly remodeled, furnished and completely renovated with new... View all property information
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    Marathon, Florida Keys 33050
    1 / 33
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • ?
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    • x
    About this property
    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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    Key West, Florida Keys 33040
    1 / 92
    Marathon Shores
    7 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    About this property
    YOUR OWN OCEANFRONT RESORT WITH A PRIVATE BEACH. Spectacular ocean views from this beautiful multi house property, with a POOL. Enjoy the ocean breeze from the main house while entertaining in an upgraded kitchen with new appliances and granite counter tops. 4 other cottages are on the property... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 22
    4 of 5 bubbles (13) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    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 / 8
    5 of 5 bubbles (3) Excellent
    Islamorada
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 28
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    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
    1 / 36
    Key Largo
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Enjoy this private air conditioned room with cable TV, Wi Fi, coffee pot. Guest uses the bathrooms/showers that are common to the RV Park wherein this private room is located. Clean Linens and towel provided by our housekeeping staff. "We enjoyed our time there very much. The room was clean and... View all property information
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    Key Largo, Florida Keys 33037
    1 / 12
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautiful Furnished, 2 bedroom 1 bath Mobile home with wrap-around gorgeous bar and covered patio, in the center of Key Largo; MM 102 Bayside Across Tradewinds Shopping Center, close to all amenities and attractions, practically across from John Penne Kamp Gated community, new beautiful pool,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 27
    4 of 5 bubbles (27) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    • x
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    About this property
    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
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    Key West, Florida Keys 33040
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    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and the Atlantic ocean.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 26
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • x
    About this property
    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Pelican Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 bubbles (21) Very good
    Key West
    Studio, 3 Bathrooms, Sleeps 7 | Quick View
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    • Terrace
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    • x
    About this property
    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    4.5 of 5 bubbles (5) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!... View all property information
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    Islamorada, Florida Keys 33036
    1 / 29
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • ?
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    • x
    About this property
    The Bougainvillea is located just steps from our heated pool and adjacent to the Hibiscus Room. Both share a large semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common space and plenty of privacy. The... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    Key West
    Studio, Sleeps 2 | Quick View
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    • x
    About this property
    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
    1 / 88
    5 of 5 bubbles (3) Excellent
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Spacious apartment in Quite street, Key Largo Recently remodeled one bedroom apartment centrally located in the Heart of Key Largo. Private, Safe and Quiet residential neighborhood within walking distance to John Pennekamp National Park. Kayak right into the parks beautiful mangrove canals and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 31
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    Key West, Florida Keys 33040
    1 / 23
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Room 6 is conveniently located on the main floor. It has a door that opens onto the side deck with a secluded sitting area. The front porch sitting area is only a few steps away. People that stay in Room six often comment on how pleasant it is to wake up to the smell of breakfast cooking nearby in... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4.5 of 5 bubbles (5) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    We offer a 34 Ft 5th Wheel with all utilities hooked up minutes away from major stores and attractions.You need not bring anything other than your cloths and snorkeling equipment.We have everything the most demanding outdoor adventurer would expect.As our guest you have access too our pool located... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 41
    4 of 5 bubbles (20) Very good
    Key West
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs large tiled walk-in shower with hair-dryer makes this private... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool...
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 / 15
    5 of 5 bubbles (1) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Internet Access
    • Private Garden
    • Washer
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Great 2/1 house. Completely renovated. Full kitchen with new stainless steel appliances: Microwave, Range/Oven, Dishwasher, Refrigerator. Central A/C & Heat. Master bedroom has queen size bed and a 32" flat screen tv. Second bedroom has a full size bed and a twin size trundle (full sleeps 2 and... View all property information
    Location Information
    Key Largo, Florida Keys 33037