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Holiday Rentals nearby Florida Keys Jet Ski Rentals

24500 Overseas Hwy, Summerland Key, Florida 33042-4614
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    Travellers to Summerland Key are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 38 Rentals in Summerland Key
    1.0 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2.5 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2.8 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.1 / 14
    (1)Very good
    0.4 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 13 March 2019
    We had a wonderful time and our living quarters were adequate. The views were great but we were disappointed that the boat dock wasn’t there and the davits were unusable (good...
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    About this property
    If you are still interested in January please contact me with a booking inquiry. Stunning Atlantic Ocean views from dining area, living room and both bedrooms. Sunrise on the left, sunset on the right and in between 180 degrees of open ocean. Our vacation home is located in exclusive Summerland...
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    Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront House1 / 51
    (1)Excellent
    0.3 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    What a find in renting this home. It’s one of the nicest we have stayed in since coming to the Keys. From the owner’s, to the manager, to the pool guy, to the grounds’ keeper...
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    About this property
    This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front of the home, was formerly...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.1 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Smoking allowed
    About this property
    This is the perfect home for an unforgettable vacation in the Florida Keys. This theme inspired home tells a tale of mermaid’s and ocean lore. The custom tile work in all 3 baths is hand made and designed to transport you to ocean vistas. The main level boasts 3 bedrooms, sleeping den, 2 baths and...
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    Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.1 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access. This home is five stars the moment you pull into the paver circular driveway. Sitting on two lots...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.0 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42' Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kitchen is a chef's delight with...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.9 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropical style with cool and comfortable leather in the...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.2 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef's dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops. The...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.3 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for friends and family....
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    Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.9 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours. The grounds are very shady and groomed with a nice Tiki hut at the waters edge. Plenty of dockage on the canal side and...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Acreage Multi-Million Dollar  Beachfront Mansion w/ Pool & Billiards1 / 48
    (1)Terrible
    1.5 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    This is a newly remodeled four bedrooms multimillion-dollar elegant mansion. The house has its own private beach located in the heart of Summerland Key. It is the perfect Key for a vacation getaway. Summerland Key is an island in the lower Florida Keys about 20 miles east of Key West. The island...
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    Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.3 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the cleanest blue water flow-thru canals in the Keys! This comfortable home is clean and conveniently located at MM 24.5 on Summerland Key, near the beginning of a deep blue water canal. This elevated CBS home has concrete floors covered in ceramic tile and new carpet in the bedrooms....
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.1 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your next vacation relaxing in the tropical splendor of this upscale, canal front home, appropriately know as Isle Be Back. Located in the desirable neighborhood of Summerland Key Cove, this spacious multi-story home offers the master bedroom and en suite bath o the uppermost floor with an...
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    Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    1.2 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Florida Keys meets Coastal Chic.This brand new and completely re-imagined Caribbean Dream vacation home in popular Summerland Key (Mile Marker 24) is truly amazing! Totally renovated with meticulous attention to detail in March of 2020. The 3300 s.f.home easily accommodates up to 10 friends or...
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    Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.6 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Children's Pool
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical Sabbatical This stilt home is located in Venture Out, a resort community on Cudjoe Key. Community amenities include a large heated pool, heated children's pool, hot tub, salt-water swimming area as well as basketball, pickleball, bocce, and tennis courts. Enjoy your stay within the resort...
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    Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GET TO THE POINTE!!! This lovely 2-bedroom 2 bath home, situated at the end of Bay Drive on both open water and corner canal, the best the Lower Keys has to offer. This newly remodeled interior has a well-equipped gourmet kitchen that will be a pleasure to create those memorable family meals. The...
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    Summerland Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.9 kilometres from Florida Keys Jet Ski Rentals
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cudjoe Landing Make yourself at home at this topical waterfront duplex and start living that Floridan life you've dreamed of! Cudjoe Landing offers its lucky guests a large open floor plan that combines the kitchen, living area, and dining room together; no one will ever feel left out here! Prepare...
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    Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    1.1 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around in and cool off...
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    Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2.6 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Central Heating
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Paradise in the comfortable island style of Catch of the Day! This 2 bedroom 2 bath canal front home on Cudjoe offers the casual lifestyle of the Lower Keys. It features all amenities including new furnishings, a well appointed kitchen and fresh linens. A large under-house storage area...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.7 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental is 28 Days to a single family or party (no subleases allowed). All pictures are post IRMA.Simply Breathtaking VIEWS of the sunset over the ocean like this right from this home and from the deck. 2 Bedroom 2 Bathroom Home with Ocean Front Views Sleeps 6. Fisherman's grand slam!...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.4 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Concrete home with canal front view. 80 foot concrete dock with easy access to the Gulf and Ocean. Lots of parking on the oversized lot . 3 screened in porches for outdoor entertaining. The home is well stocked with everything you’ll need to enjoy your stay. This is a 28 day minimum rental....
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming 3bedroom/2bath home in the Florida Keys1 / 21
    (3)Very good
    2.6 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2016
    I would recommend this house to anyone the house is clean and comfortable, stocked with evrything you will need. The loacation is perfect, your located about 15 minutes from...
    Reviewed 21 October 2015
    This was a last minute change of plans to rent this home and we could not have been any more pleased. The home was clean, very inviting and I truly felt like I was staying at my...
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    About this property
    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This great Vacation Home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms provide ideal entertaining areas for friends and family. Enjoy warm, tropical breezes on the large wood dock, overlooking the deepwater canal, perfect for swimming and...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Ocean Views
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at this tropical style 2 bedroom, 2 bathroom home in Venture Out. Located in a gated community with all the amenities you will need for any Florida Keys vacation, including a marina with a store, 2 boat ramps, and easy access to the Gulf or Atlantic Ocean side. When you are not boating,...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.8 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Terrace
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    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at this heavenly oasis. Pull up to a fully fenced 2 bedroom, 2 bathroom Florida Keys home. The front parking area provides parking for you AND your guests. In addition, there is plenty of space to park your water toys on the 60’ of dockage. The home offers beautfiul, vaulted wood...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.9 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    It's always 5 O'Clock here at this wonderful Florida Keys vacation spot. Start your day off with refreshing Mimosas or Bloody Marys as you enjoy sitting out on the screened porch overlooking the nice boating canal. The interior is nicely decorated in tropical island style with lovely accents to...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.6 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to Looe Key, site of some of...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2.8 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get togethers. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate Island home. Home-away-from-home comforts include central air and a well equipped kitchen. The 30' dockage area provides quick and easy access to the best fishing and diving in...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Balcony
    • Waterfront
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated 3 bedroom/2 bath home, sleeps 8. Enjoy early morning coffee or evenings gazing at the stars from the cozy balcony. Downstairs area also has space for relaxing, grilling or simply putting all your fishing equipment together. Our Island House is on a canal leading within minutes to...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.6 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled canal-front home on Cudjoe Key. Remodel includes new floors throughout (bamboo hardwood and tile), chef's kitchen with island and stainless appliances, ceiling fans throughout and new a/c. Brand new couch and chair (not pictured). The house has a new roof, stairs, siding,...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.4 kilometres from Florida Keys Jet Ski Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lazy Lagoon Gaze out onto the water from beside your own private pool. It's possible at this quintessential Keys home! Guests bringing along their boats will love staying in a space with a 64 foot concrete dock, a boat davit, and a fish cleaning table. There's even a swimming ladder for if you feel...
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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.1 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Per the Governor of Florida, effective June 1, 2020 vacation rentals will be allowed in Monroe County with the following new guidelines. Under these new guidelines, reservations from COVID-19 hot spots identified by the Governor are to be avoided. COVID-19 identified hotspots according to the...
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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.4 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Terrace
    • Waterfront
    • Ocean Views
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A clean, wide canal with immediate access to Kemp Channel makes this home a terrific choice for boaters, fisherman and divers alike! Situated on Wahoo Lane, Cudjoe, this comfortable 3-bedroom 2 bath stilt home provides, the outdoor island lifestyle; upstairs 2 wide open decks on either side of a...
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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 kilometres from Florida Keys Jet Ski Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Getaway Make this waterfront Florida retreat your next home away from home and come and experience a true beach getaway! On the first floor of Caribbean Getaway, you'll find a convenient living area next to some of the bedrooms available. Right off the living area is the marvelous outdoor...
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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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