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Sugarloaf Key Holiday Rentals

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23 rentals in Sugarloaf Key.
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Key West: 3 BR, 2 BA Luxury Yacht; Special Now!, holiday rental in Sugarloaf Key

Key West: 3 BR, 2 BA Luxury Yacht; Special Now!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful quiet neighborhood.  Sunsets!  Huge pool! 10 min to Key West, holiday rental in Sugarloaf Key

Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West

3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront home with open water view, dock, hot tub, private beach, dog friendly, holiday rental in Sugarloaf Key

Waterfront home with open water view, dock, hot tub, private beach, dog friendly

3 bedrooms
2 bathrooms
Sleeps 8
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**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., holiday rental in Sugarloaf Key

**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES..

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beach House at Sugarloaf Key w/430ft dock 5ft drft (teal house), holiday rental in Sugarloaf Key

Beach House at Sugarloaf Key w/430ft dock 5ft drft (teal house)

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SUGARLOAF KEY Home on Wide Canal - 4 Bedroom, 2 Bath with Pool, holiday rental in Sugarloaf Key

SUGARLOAF KEY Home on Wide Canal - 4 Bedroom, 2 Bath with Pool

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, holiday rental in Sugarloaf Key

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks

5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Casa Mahi - Sea, Nature, & Relax, holiday rental in Sugarloaf Key

Casa Mahi - Sea, Nature, & Relax

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquility in Paradise - Sugarloaf, holiday rental in Sugarloaf Key

Tranquility in Paradise - Sugarloaf

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Large, dog-friendly home on three secluded acres w/ balconies, deck, views, holiday rental in Sugarloaf Key

Large, dog-friendly home on three secluded acres w/ balconies, deck, views

5 bedrooms
4 bathrooms
Sleeps 10
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Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, holiday rental in Sugarloaf Key

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks

5 bedrooms
3 bathrooms
Sleeps 18
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3 Bedroom 2 Bath , Canal Front with Pool, holiday rental in Sugarloaf Key

3 Bedroom 2 Bath , Canal Front with Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish condo with shared swimming pool moments from popular attractions!, holiday rental in Sugarloaf Key

Stylish condo with shared swimming pool moments from popular attractions!

2 bedrooms
3 bathrooms
Sleeps 4
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Sea View Terrace near Key West Gulf Flats Fishing Ocean Mangrove Channels Kayaks, holiday rental in Sugarloaf Key

Sea View Terrace near Key West Gulf Flats Fishing Ocean Mangrove Channels Kayaks

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean’s Edge Retreat, holiday rental in Sugarloaf Key

Ocean’s Edge Retreat

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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#SUGARFOOT_SUNSETS private beach,ServiceLift,Pool,Tiki,Dock, LOW BARRIER ACCESS, holiday rental in Sugarloaf Key

#SUGARFOOT_SUNSETS private beach,ServiceLift,Pool,Tiki,Dock, LOW BARRIER ACCESS

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Welcoming home w/ private pool & covered porch - walk to dining & attractions, holiday rental in Sugarloaf Key

Welcoming home w/ private pool & covered porch - walk to dining & attractions

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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It's time to get away!, holiday rental in Sugarloaf Key

It's time to get away!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Canalfront Home - The Perfect Keys Getaway!, holiday rental in Sugarloaf Key

Canalfront Home - The Perfect Keys Getaway!

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, holiday rental in Sugarloaf Key

Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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New listing! Waterfront dream home w/ a private, heated pool, deck & dock, holiday rental in Sugarloaf Key

New listing! Waterfront dream home w/ a private, heated pool, deck & dock

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to our Mid Century Bungalow on the water, holiday rental in Sugarloaf Key

Welcome to our Mid Century Bungalow on the water

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tropical Village Retreat - Beautifully Updated Condo w/ On Site Heated Pool., holiday rental in Sugarloaf Key

Tropical Village Retreat - Beautifully Updated Condo w/ On Site Heated Pool.

2 bedrooms
1 bathroom
Sleeps 4
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