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Sugarloaf Holiday Rentals

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50 rentals in Sugarloaf.
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For up to date Information call owner Patrick Bailey *******-5000
4 bedrooms
3 bathrooms
Sleeps 8
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South Point Shores
3 bedrooms
2 bathrooms
Sleeps 6
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Bow Channel Manor
3 bedrooms
3 bathrooms
Sleeps 6
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Bay Pointe
3 bedrooms
3 bathrooms
Sleeps 6
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Dolphin Bay
2 bedrooms
2 bathrooms
Sleeps 6
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Florida Keys at it's best
3 bedrooms
3 bathrooms
Sleeps 6
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Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, FirePit, Bikes
2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5
2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful home in oceanfront resort with pool & dock, 16 miles from Key West
2 bedrooms
3 bathrooms
Sleeps 6
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REDUCED SPRING RATES! Private Home in Waterfront Community Pool Kayaks Bikes
2 bedrooms
3 bathrooms
Sleeps 6
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Save time - get the best Sugarloaf rentals sent straight to your email!
Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West
3 bedrooms
2 bathrooms
Sleeps 8
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Lovely Furnished Home in Oceanfront Community w/Shared Boat Docks, Pool & Beac
2 bedrooms
3 bathrooms
Sleeps 6
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Peaceful and Ocean View Estate 15 minutes from Key West
3 bedrooms
2 bathrooms
Sleeps 12
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4 other travellers have booked this property
Fandango
5 bedrooms
3 bathrooms
Sleeps 14
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1 other traveller has booked this property
Tropical Paradise Oceanfront Home with Pool
2 bedrooms
2 bathrooms
Sleeps 6
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**VILLA OF THE SETTING SUN * THE BAY** Waterfront & Pool + LAST KEY SERVICES...
4 bedrooms
4 bathrooms
Sleeps 8
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
2 bedrooms
2 bathrooms
Sleeps 6
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Family Retreat-Ocean front home with private pool
6 bedrooms
4 bathrooms
Sleeps 14
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Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak
3 bedrooms
2 bathrooms
Sleeps 7
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Waterfront home with open water view, dock, hot tub, private beach, dog friendly
3 bedrooms
2 bathrooms
Sleeps 8
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Blue Palms Retreat. ocean front w/pool and dock for your boat.
3 bedrooms
2 bathrooms
Sleeps 8
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**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES..
4 bedrooms
3 bathrooms
Sleeps 10
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SUGARLOAF KEY Home on Wide Canal - 4 Bedroom, 2 Bath with Pool
4 bedrooms
2 bathrooms
Sleeps 10
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Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house)
2 bedrooms
3 bathrooms
Sleeps 8
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Casa Mahi - Sea, Nature, & Relax
3 bedrooms
3 bathrooms
Sleeps 6
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Tropical Island House ,
3 bedrooms
3 bathrooms
Sleeps 10
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Blue vacation home, water front, boat dock, heated private Pool.
4 bedrooms
2 bathrooms
Sleeps 8
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3 other travellers have booked this property
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks
5 bedrooms
3 bathrooms
Sleeps 18
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Charming Artist Home - Canal Front - Deep Water 40’ Dock!
3 bedrooms
3 bathrooms
Sleeps 6
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2 Bedroom/3 Bath Waterfront 28 day rental
2 bedrooms
3 bathrooms
Sleeps 4
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Palm Harbor
3 bedrooms
2 bathrooms
Sleeps 8
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Keys Escape
3 bedrooms
3 bathrooms
Sleeps 6
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Large, dog-friendly home on three secluded acres w/ balconies, deck, views
5 bedrooms
4 bathrooms
Sleeps 10
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4 other travellers have booked this property
Paradise on Cudjoe Bay
2 bedrooms
3 bathrooms
Sleeps 6
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6 other travellers have booked this property
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks
5 bedrooms
3 bathrooms
Sleeps 18
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Yellow vacation home, water view, boat dock, heated private pool.
3 bedrooms
2 bathrooms
Sleeps 6
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3 Bedroom 2 Bath , Canal Front with Pool
3 bedrooms
2 bathrooms
Sleeps 6
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Ocean’s Edge Retreat Waterfront Home W/ Boat Dock
2 bedrooms
3 bathrooms
Sleeps 6
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Canalfront Home - The Perfect Keys Getaway!
3 bedrooms
2 bathrooms
Sleeps 9
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Florida Keys Home 15 minutes from Key West with deep water access.
3 bedrooms
2 bathrooms
Sleeps 6
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#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI
5 bedrooms
2 bathrooms
Sleeps 12
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Tranquility in Paradise - Cudjoe
3 bedrooms
2 bathrooms
Sleeps 8
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Tranquility in Paradise - Sugarloaf
5 bedrooms
3 bathrooms
Sleeps 10
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BRAND NEW WATERFRONT 3/2
3 bedrooms
2 bathrooms
Sleeps 8
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Welcome to our Mid Century Bungalow on the water
1 bedroom
1 bathroom
Sleeps 4
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It's time to get away!
3 bedrooms
2 bathrooms
Sleeps 10
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New listing! Waterfront dream home w/ a private, heated pool, deck & dock
2 bedrooms
2 bathrooms
Sleeps 6
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Villa and guest house with shared pool, central AC, internet, and washer/dryer
6 bedrooms
5 bathrooms
Sleeps 16
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Bright, spacious home with shared pool, internet, private washer/dryer, & loft!
4 bedrooms
4 bathrooms
Sleeps 12
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Oceanfront home-swimming pool-boat ramp-dockage-just 20 miles from Key West
3 bedrooms
2 bathrooms
Sleeps 6
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