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Sugarloaf Vacation Rentals

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50 rentals in Sugarloaf.
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New Listing!!! Paradise Point - Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf
New Listing!!! Paradise Point - Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf
New Listing!!! Paradise Point - Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf

New Listing!!! Paradise Point - Luxurious Open Water Home W/ Pool, Tiki, Dockage

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Palms Resort at Sugarloaf - Grey House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf - Grey House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf - Grey House, vacation rental in Sugarloaf

Palms Resort at Sugarloaf - Grey House

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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For up to date Information call owner Patrick Bailey *******-5000, vacation rental in Sugarloaf
For up to date Information call owner Patrick Bailey *******-5000, vacation rental in Sugarloaf
For up to date Information call owner Patrick Bailey *******-5000, vacation rental in Sugarloaf

For up to date Information call owner Patrick Bailey *******-5000

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bow Channel Manor, vacation rental in Sugarloaf
Bow Channel Manor, vacation rental in Sugarloaf
Bow Channel Manor, vacation rental in Sugarloaf

Bow Channel Manor

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf
PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf
PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage, vacation rental in Sugarloaf

PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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South Point Shores, vacation rental in Sugarloaf
South Point Shores, vacation rental in Sugarloaf
South Point Shores, vacation rental in Sugarloaf

South Point Shores

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Pointe, vacation rental in Sugarloaf
Bay Pointe, vacation rental in Sugarloaf
Bay Pointe, vacation rental in Sugarloaf

Bay Pointe

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Florida Keys at it's best, vacation rental in Sugarloaf
Florida Keys at it's best, vacation rental in Sugarloaf
Florida Keys at it's best, vacation rental in Sugarloaf

Florida Keys at it's best

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf
BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf
BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf

BRAND NEW WATERFRONT 3/2

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Sugarloaf
White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Sugarloaf
White Vacation home, Private Boat Dockage, Heated Private Pool., vacation rental in Sugarloaf

White Vacation home, Private Boat Dockage, Heated Private Pool.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wonderful, pet friendly, smart home with plenty of paddle toys, vacation rental in Sugarloaf
Wonderful, pet friendly, smart home with plenty of paddle toys, vacation rental in Sugarloaf
Wonderful, pet friendly, smart home with plenty of paddle toys, vacation rental in Sugarloaf

Wonderful, pet friendly, smart home with plenty of paddle toys

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf
Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf
Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf

Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ocean View Estate with Private Pool 15 minutes from Key West , vacation rental in Sugarloaf
Ocean View Estate with Private Pool 15 minutes from Key West , vacation rental in Sugarloaf
Ocean View Estate with Private Pool 15 minutes from Key West , vacation rental in Sugarloaf

Ocean View Estate with Private Pool 15 minutes from Key West

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf

The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Paradise Oceanfront Home with Pool, vacation rental in Sugarloaf
Tropical Paradise Oceanfront Home with Pool, vacation rental in Sugarloaf
Tropical Paradise Oceanfront Home with Pool, vacation rental in Sugarloaf

Tropical Paradise Oceanfront Home with Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming cottages, dockage, pool, kayaks, just minutes to Key West, vacation rental in Sugarloaf
Charming cottages, dockage, pool, kayaks, just minutes to Key West, vacation rental in Sugarloaf
Charming cottages, dockage, pool, kayaks, just minutes to Key West, vacation rental in Sugarloaf

Charming cottages, dockage, pool, kayaks, just minutes to Key West

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf
Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf
Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf
Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf
Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf

Casa Mahi - Sea, Nature, & Relax

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Welcome to our Mid Century Bungalow on the water, vacation rental in Sugarloaf
Welcome to our Mid Century Bungalow on the water, vacation rental in Sugarloaf
Welcome to our Mid Century Bungalow on the water, vacation rental in Sugarloaf

Welcome to our Mid Century Bungalow on the water

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf
**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf
**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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It's time to get away!, vacation rental in Sugarloaf
It's time to get away!, vacation rental in Sugarloaf
It's time to get away!, vacation rental in Sugarloaf

It's time to get away!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront Paradise!, vacation rental in Sugarloaf
Oceanfront Paradise!, vacation rental in Sugarloaf
Oceanfront Paradise!, vacation rental in Sugarloaf

Oceanfront Paradise!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf
Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf
Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf

Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf
Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf
Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf
3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf
3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf

3 Bedroom 2 Bath , Canal Front with Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue vacation home, water front, boat dock, heated private Pool., vacation rental in Sugarloaf
Blue vacation home, water front, boat dock, heated private Pool., vacation rental in Sugarloaf
Blue vacation home, water front, boat dock, heated private Pool., vacation rental in Sugarloaf

Blue vacation home, water front, boat dock, heated private Pool.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Sugarloaf
2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Sugarloaf
2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Sugarloaf

2 Bedroom/3 Bath Waterfront 28 day rental

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water, vacation rental in Sugarloaf
Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water, vacation rental in Sugarloaf
Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water, vacation rental in Sugarloaf

Stylish & Beautiful Home on Pristine Canal, 4 Minutes to Open Water

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Yellow vacation home, water view, boat dock, heated private pool., vacation rental in Sugarloaf
Yellow vacation home, water view, boat dock, heated private pool., vacation rental in Sugarloaf
Yellow vacation home, water view, boat dock, heated private pool., vacation rental in Sugarloaf

Yellow vacation home, water view, boat dock, heated private pool.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet friendly amazing location in paradise, vacation rental in Sugarloaf
Pet friendly amazing location in paradise, vacation rental in Sugarloaf
Pet friendly amazing location in paradise, vacation rental in Sugarloaf

Pet friendly amazing location in paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Magnificent 3 Bedroom 2 Bath with plenty of dock space and new pool soon!, vacation rental in Sugarloaf
Magnificent 3 Bedroom 2 Bath with plenty of dock space and new pool soon!, vacation rental in Sugarloaf
Magnificent 3 Bedroom 2 Bath with plenty of dock space and new pool soon!, vacation rental in Sugarloaf

Magnificent 3 Bedroom 2 Bath with plenty of dock space and new pool soon!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf
Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf
Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf

Spectacular Open Water Hawaiian Style Home for the Savvy Traveler

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf

#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Tranquility in Paradise - Cudjoe, vacation rental in Sugarloaf
Tranquility in Paradise - Cudjoe, vacation rental in Sugarloaf
Tranquility in Paradise - Cudjoe, vacation rental in Sugarloaf

Tranquility in Paradise - Cudjoe

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tranquility in Paradise - Sugarloaf, vacation rental in Sugarloaf
Tranquility in Paradise - Sugarloaf, vacation rental in Sugarloaf
Tranquility in Paradise - Sugarloaf, vacation rental in Sugarloaf

Tranquility in Paradise - Sugarloaf

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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3/2  Cudjoe Key waterfront single level house., vacation rental in Sugarloaf
3/2  Cudjoe Key waterfront single level house., vacation rental in Sugarloaf
3/2  Cudjoe Key waterfront single level house., vacation rental in Sugarloaf

3/2 Cudjoe Key waterfront single level house.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom accommodation in Summerland Key, vacation rental in Sugarloaf
3 bedroom accommodation in Summerland Key, vacation rental in Sugarloaf
3 bedroom accommodation in Summerland Key, vacation rental in Sugarloaf

3 bedroom accommodation in Summerland Key

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanside, pet friendly, smart home with plenty of paddle equipment, vacation rental in Sugarloaf
Oceanside, pet friendly, smart home with plenty of paddle equipment, vacation rental in Sugarloaf
Oceanside, pet friendly, smart home with plenty of paddle equipment, vacation rental in Sugarloaf

Oceanside, pet friendly, smart home with plenty of paddle equipment

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bring Your Boat, vacation rental in Sugarloaf
Bring Your Boat, vacation rental in Sugarloaf
Bring Your Boat, vacation rental in Sugarloaf

Bring Your Boat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary Sportsman's Paradise, $8,950 month, vacation rental in Sugarloaf
Contemporary Sportsman's Paradise, $8,950 month, vacation rental in Sugarloaf
Contemporary Sportsman's Paradise, $8,950 month, vacation rental in Sugarloaf

Contemporary Sportsman's Paradise, $8,950 month

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, vacation rental in Sugarloaf
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, vacation rental in Sugarloaf
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, vacation rental in Sugarloaf

Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers

Rental Home
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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3 bedroom accommodation in Key West, vacation rental in Sugarloaf
3 bedroom accommodation in Key West, vacation rental in Sugarloaf
3 bedroom accommodation in Key West, vacation rental in Sugarloaf

3 bedroom accommodation in Key West

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ground level home in Cudjoe Gardens with heated pool, boat dock & RV parking, vacation rental in Sugarloaf
Ground level home in Cudjoe Gardens with heated pool, boat dock & RV parking, vacation rental in Sugarloaf
Ground level home in Cudjoe Gardens with heated pool, boat dock & RV parking, vacation rental in Sugarloaf

Ground level home in Cudjoe Gardens with heated pool, boat dock & RV parking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf
Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf
Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cassie's Paradise, vacation rental in Sugarloaf
Cassie's Paradise, vacation rental in Sugarloaf
Cassie's Paradise, vacation rental in Sugarloaf

Cassie's Paradise

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Sugarloaf
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Sugarloaf
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Sugarloaf

New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front Paradise Awaits!, vacation rental in Sugarloaf
Ocean Front Paradise Awaits!, vacation rental in Sugarloaf
Ocean Front Paradise Awaits!, vacation rental in Sugarloaf

Ocean Front Paradise Awaits!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Listing!!! BREEZY PALMS - Beautiful Open Water Oasis, Spectacular Views, Doc, vacation rental in Sugarloaf
New Listing!!! BREEZY PALMS - Beautiful Open Water Oasis, Spectacular Views, Doc, vacation rental in Sugarloaf
New Listing!!! BREEZY PALMS - Beautiful Open Water Oasis, Spectacular Views, Doc, vacation rental in Sugarloaf

New Listing!!! BREEZY PALMS - Beautiful Open Water Oasis, Spectacular Views, Doc

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Sugarloaf


Yes, here are some popular vacation rentals in Sugarloaf that have internet access:\n\nSee all vacation rentals in Sugarloaf on Tripadvisor