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Holiday Rentals near Skydive Key West

5 Bat Tower Rd, Sugarloaf Airport, Sugarloaf, Florida 33042-3690
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    Don't let other travellers get your favourite Sugarloaf area holiday rental. You're so close to securing your perfect getaway. Book today.
    15 Matching Rentals in the Sugarloaf AreaView all 22 rentals
    Sugarloaf
    1.7 kilometres from Skydive Key West
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Sugarloaf
    1.3 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sugarloaf
    1.5 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sugarloaf
    3.3 kilometres from Skydive Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf
    4.7 kilometres from Skydive Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    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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    Location Information
    Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf
    0.9 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Situated on 475 feet of lush canal frontage, this gated 3BR/2BA provides a luxurious getaway with panoramic views of Sugarloaf Sound. Highlights of the property include prime outdoor entertaining space and a spacious floor plan furnished in a beachy style. Your backyard oasis...
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    Location Information
    Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 15 kilometres of Sugarloaf.
    Summerland Key
    7.6 kilometres from Skydive Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family Retreat ocean front home with private pool1 / 25
    (15)Very good
    Cudjoe Key
    7.7 kilometres from Skydive Key West
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 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 21 December 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Fandango1 / 30
    (12)Excellent
    Cudjoe Key
    7.6 kilometres from Skydive Key West
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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 8 August 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 9 December 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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Tropical Paradise Oceanfront Home with Pool1 / 25
    (10)Excellent
    Cudjoe Key
    7.6 kilometres from Skydive Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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 17 March 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 19 July 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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oksana's Tropical Beach Oasis1 / 22
    (2)Excellent
    Cudjoe Key
    8.0 kilometres from Skydive Key West
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 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 2 May 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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Cudjoe Key
    7.1 kilometres from Skydive Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cudjoe Key
    7.1 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    7.1 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Palms Retreat (formerly known as Heron's Roost)1 / 24
    (2)Excellent
    Cudjoe Key
    7.8 kilometres from Skydive Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 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 23 August 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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    Location Information
    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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