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Vacation Rentals near Backcountry Boat Rentals

17015 Overseas Hwy, Sugarloaf Key, Florida 33042-3681
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    Travelers to Sugarloaf Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 26 Rentals in Sugarloaf Key
    2.1 miles from Backcountry Boat Rentals
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    2.2 miles from Backcountry Boat Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2.6 miles from Backcountry Boat Rentals
    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    4.5 miles from Backcountry Boat Rentals
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 miles in the other. This 1200...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.9 miles from Backcountry Boat Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay! This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living. Complete with a Gourmet Kitchen of stainless steel appliances and granite counters making entertaining a breeze....
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    Cudjoe Key, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.4 miles from Backcountry Boat Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.4 miles from Backcountry Boat Rentals
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West...
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oksana's Tropical Beach Oasis1 / 22
    (2)Excellent
    4.5 miles from Backcountry Boat Rentals
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 2017
    The house is very nice. They are upgrading many of the rooms...the kitchen is really nice. The view is spectacular and the large backyard is great. The fact that they allow...
    Reviewed May 1, 2016
    Our family of 3 couples and 2 singles stayed here in April and loved it. Rental process was smooth, management very nice and provided local info on places to eat and things to...
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    About this property
    Oksana's Tropical Beach Oasis is a spacious ocean front property with spectacular views and a large swimming pool with overflow spa. The beach area has not been dug out by man. We recommend you bring swim shoes to walk around in that area. The dock is currently under repairs after Hurricane Irma...
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    Cudjoe Key, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    2.4 miles from Backcountry Boat Rentals
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.5 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Vista Estate Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV...
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    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.3 miles from Backcountry Boat Rentals
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Vacation home sits behind some mangroves and has a view over Cudjoe Bay to the Atlantic. 4 bedroom and 2 bathrooms. Large deck with water access for a small boat. Water access has a shallow area to and from the deep area the boat would be docked at. Vacation home sits far off of the main road for a...
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    Summerland Key, Lower Keys
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West's only Real Beach House1 / 11
    (4)Excellent
    2.5 miles from Backcountry Boat Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2017
    Words will never be able to convey how beautiful, tranquil, peaceful, and perfect Sea Vista Estate is. I am literally "homesick" to go back, and we've been home a mere...
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    About this property
    Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished...
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    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Family Retreat ocean front home with private pool1 / 25
    (15)Very good
    4.3 miles from Backcountry Boat Rentals
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2018
    Nice large house with plenty of space .Not much Beach or Access to fishing without a Boat as the water is very shallow in this whole area. Easy drive to whatever you are wanting.
    Reviewed December 21, 2017
    This is the PERFECT Family retreat! Each year, my husband and I take our 5 grown kids and their significant others to the Keys for a family vacation. We've tried multiple...
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    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. New memory foam mattresses in 2018....
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    Cudjoe Key, Florida Keys
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Tropical Paradise Oceanfront Home with Pool1 / 24
    (10)Excellent
    4.3 miles from Backcountry Boat Rentals
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2017
    Our family of four loved everything about this property - the location, the kayaks and bikes that are provided, Cudjoe Bay (which is just steps from the deck), the view! So...
    Reviewed July 19, 2016
    I had originally reserved a larger house a few streets down from this one. That was when there was going to be a much larger group. However, due to the fact that some friends...
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    About this property
    Paradise found, this house has it all, beach, dipping pool, screened in porch, kayaks, bikes, floating dock and amazing views. This has been a popular honeymoon and anniversary celebration home for over 15 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.5 miles from Backcountry Boat Rentals
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Yard
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants the Florida Keys has to...
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    Key West, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4.0 miles from Backcountry Boat Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for friends to gather. Full walk around screened...
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    Cudjoe Key, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugarloaf Key is one of the most desirable islands in the Lower Keys. Large roomy lots, plenty of biking and walking trails in the area. Kayaking , boating and diving are just some of the water sports you will enjoy during your stay. Green Turtle Landing is just the right spot to spend your Florida...
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    Sugarloaf, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.2 miles from Backcountry Boat Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second...
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    Sugarloaf, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.6 miles from Backcountry Boat Rentals
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key. The grounds are like a playground. There is a full-size heated pool with...
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    Sugarloaf, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.6 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright, very spacious and inviting, nicely-maintained Sugarloaf Key home is located just 20 minutes north of Key West. Nestled back in a beautifully manicured neighborhood and not far from Sugarloaf Lodge and Marina, you will have nearby access to boating, fishing, kayaking and a few local...
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    Location Information
    Sugarloaf, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.0 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! The kitchen is fully equipped with all the luxuries of home (and more!). The dockside Tiki Hut and hammock overlook a great, deepwater canal perfect for boating and swimming. This vacation rental home...
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    Location Information
    Cudjoe Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.0 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft. Large and spacious inside with open...
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    Cudjoe Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blue Palms Retreat (formerly known as Heron's Roost)1 / 24
    (2)Excellent
    4.4 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2018
    The house was clean, up to date, and very comfortable. The furniture under the house was great, as we could sip on cold drinks in the shade and still have a view of the ocean...
    Reviewed August 23, 2018
    We so enjoyed staying at Blue Palms Retreat. The views from the house were simply breathtaking. We enjoyed lounging by the pool and hanging out in the gazaebo. Fishing was...
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    About this property
    This house is a charmer. 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key. Large, heated swimming pool with shaded hang out area and ping pong table. Double kayak and hammock provided. Bikes and paddle boards available for rent. Charming character with hand made pottery...
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    Cudjoe Key, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fandango1 / 24
    (12)Excellent
    4.3 miles from Backcountry Boat Rentals
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2017
    Our family and friends had an amazing week at Fandango. Everything from the location, to the amenities was perfect. The house had all you needed to create unforgettable family...
    Reviewed December 8, 2016
    My daughter-in-law leased Fandango House for 3 days to celebrate the birthdays of my two children and myself. Fandango is a beautifully kept vacation rental that has all the...
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    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks....
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    Cudjoe Key, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    0.6 miles from Backcountry Boat Rentals
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Waterfront
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This pet-friendly home completed in 2012 has 5 rooms, 3 king size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep...
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    Sugarloaf, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    2.5 miles from Backcountry Boat Rentals
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West is...
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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