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Sugarloaf Key Vacation Rentals

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33 rentals in Sugarloaf Key.
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The Conch Farmhouse

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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EASY LIVING Magnificent Private Home, Private Pool, Outdoor Dining, BBQ, vacation rental in Sugarloaf Key
EASY LIVING Magnificent Private Home, Private Pool, Outdoor Dining, BBQ, vacation rental in Sugarloaf Key
EASY LIVING Magnificent Private Home, Private Pool, Outdoor Dining, BBQ, vacation rental in Sugarloaf Key

EASY LIVING Magnificent Private Home, Private Pool, Outdoor Dining, BBQ

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Key West: 3 BR, 2 BA Luxury Yacht; Special Now!, vacation rental in Sugarloaf Key
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!, vacation rental in Sugarloaf Key
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!, vacation rental in Sugarloaf Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!, vacation rental in Sugarloaf Key
DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!, vacation rental in Sugarloaf Key
DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!, vacation rental in Sugarloaf Key

DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf Key
Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf Key
Thanksgiving available! Sugarloaf Key Open Water Home With Beach, Dock, Canal, vacation rental in Sugarloaf Key

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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A PLACE IN PARADISE Spacious, Private Home, Shared Pool, Walk to Everything!, vacation rental in Sugarloaf Key
A PLACE IN PARADISE Spacious, Private Home, Shared Pool, Walk to Everything!, vacation rental in Sugarloaf Key
A PLACE IN PARADISE Spacious, Private Home, Shared Pool, Walk to Everything!, vacation rental in Sugarloaf Key

A PLACE IN PARADISE Spacious, Private Home, Shared Pool, Walk to Everything!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Water Front Property*Saltwater Pool*Gated*Boat Dock, vacation rental in Sugarloaf Key
Water Front Property*Saltwater Pool*Gated*Boat Dock, vacation rental in Sugarloaf Key
Water Front Property*Saltwater Pool*Gated*Boat Dock, vacation rental in Sugarloaf Key

Water Front Property*Saltwater Pool*Gated*Boat Dock

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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PARROT PERCH Spacious, Family Friendly, Private Balcony, Shared Pool, Modern, vacation rental in Sugarloaf Key
PARROT PERCH Spacious, Family Friendly, Private Balcony, Shared Pool, Modern, vacation rental in Sugarloaf Key
PARROT PERCH Spacious, Family Friendly, Private Balcony, Shared Pool, Modern, vacation rental in Sugarloaf Key

PARROT PERCH Spacious, Family Friendly, Private Balcony, Shared Pool, Modern

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf Key
Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf Key
Waterfront home with open water view, dock, hot tub, private beach, dog friendly, vacation rental in Sugarloaf Key

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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KEY WEST FOUND Historic Truman Annex, Downtown, Walk to Duval, Shared Pool, vacation rental in Sugarloaf Key
KEY WEST FOUND Historic Truman Annex, Downtown, Walk to Duval, Shared Pool, vacation rental in Sugarloaf Key
KEY WEST FOUND Historic Truman Annex, Downtown, Walk to Duval, Shared Pool, vacation rental in Sugarloaf Key

KEY WEST FOUND Historic Truman Annex, Downtown, Walk to Duval, Shared Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEACH HOUSE CONDO Cozy, Charming, Spacious, Shared Pool, Walk to All!, vacation rental in Sugarloaf Key
BEACH HOUSE CONDO Cozy, Charming, Spacious, Shared Pool, Walk to All!, vacation rental in Sugarloaf Key
BEACH HOUSE CONDO Cozy, Charming, Spacious, Shared Pool, Walk to All!, vacation rental in Sugarloaf Key

BEACH HOUSE CONDO Cozy, Charming, Spacious, Shared Pool, Walk to All!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Conch Wind Private Condo, Shared Pool, Gated Community, Nestled in Old Town, vacation rental in Sugarloaf Key
Conch Wind Private Condo, Shared Pool, Gated Community, Nestled in Old Town, vacation rental in Sugarloaf Key
Conch Wind Private Condo, Shared Pool, Gated Community, Nestled in Old Town, vacation rental in Sugarloaf Key

Conch Wind Private Condo, Shared Pool, Gated Community, Nestled in Old Town

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf Key
Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf Key
Casa Mahi - Sea, Nature, & Relax, vacation rental in Sugarloaf Key

Casa Mahi - Sea, Nature, & Relax

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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TRUMAN'S HIDEAWAY  Huge Patio, Grill, Shared Pool, Family Fun + Sunset View, vacation rental in Sugarloaf Key
TRUMAN'S HIDEAWAY  Huge Patio, Grill, Shared Pool, Family Fun + Sunset View, vacation rental in Sugarloaf Key
TRUMAN'S HIDEAWAY  Huge Patio, Grill, Shared Pool, Family Fun + Sunset View, vacation rental in Sugarloaf Key

TRUMAN'S HIDEAWAY Huge Patio, Grill, Shared Pool, Family Fun + Sunset View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf Key
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf Key
Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks, vacation rental in Sugarloaf Key

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 Key
Welcome to our Mid Century Bungalow on the water, vacation rental in Sugarloaf Key
Welcome to our Mid Century Bungalow on the water, vacation rental in Sugarloaf Key

Welcome to our Mid Century Bungalow on the water

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Sugarloaf Key
Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Sugarloaf Key
Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!, vacation rental in Sugarloaf Key

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

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf Key
Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf Key
Beach House at Sugarloaf Key w/430ft dock 5ft drft (green house), vacation rental in Sugarloaf Key

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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Oceanfront Paradise!, vacation rental in Sugarloaf Key
Oceanfront Paradise!, vacation rental in Sugarloaf Key
Oceanfront Paradise!, vacation rental in Sugarloaf Key

Oceanfront Paradise!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf Key
**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf Key
**OFF THE GRID * BAYPOINT** Waterfront Home + Beach & Pool + LAST KEY SERVICES.., vacation rental in Sugarloaf Key

**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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LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All, vacation rental in Sugarloaf Key
LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All, vacation rental in Sugarloaf Key
LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All, vacation rental in Sugarloaf Key

LAVENDER JUNGLE Whimsical Vibe, Large Outdoor Space, Shared Pool, Walk to All

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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It's time to get away!, vacation rental in Sugarloaf Key
It's time to get away!, vacation rental in Sugarloaf Key
It's time to get away!, vacation rental in Sugarloaf Key

It's time to get away!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf Key
Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf Key
Upgraded Home on Water- Boat Dockage- Pool-No Contact Check-In, vacation rental in Sugarloaf Key

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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3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf Key
3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf Key
3 Bedroom 2 Bath , Canal Front with Pool, vacation rental in Sugarloaf Key

3 Bedroom 2 Bath , Canal Front with Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cassie's Paradise, vacation rental in Sugarloaf Key
Cassie's Paradise, vacation rental in Sugarloaf Key
Cassie's Paradise, vacation rental in Sugarloaf Key

Cassie's Paradise

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge Pool!, vacation rental in Sugarloaf Key

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf Key
Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf Key
Spectacular Open Water Hawaiian Style Home for the Savvy Traveler, vacation rental in Sugarloaf Key

Spectacular Open Water Hawaiian Style Home for the Savvy Traveler

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

Tranquility in Paradise - Sugarloaf

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf Key
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf Key
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, vacation rental in Sugarloaf Key

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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Ocean Front Paradise Awaits!, vacation rental in Sugarloaf Key
Ocean Front Paradise Awaits!, vacation rental in Sugarloaf Key
Ocean Front Paradise Awaits!, vacation rental in Sugarloaf Key

Ocean Front Paradise Awaits!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Tropical Village Retreat - Beautifully Updated Condo w/ On Site Heated Pool., vacation rental in Sugarloaf Key
Tropical Village Retreat - Beautifully Updated Condo w/ On Site Heated Pool., vacation rental in Sugarloaf Key
Tropical Village Retreat - Beautifully Updated Condo w/ On Site Heated Pool., vacation rental in Sugarloaf Key

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pet friendly amazing location in paradise, vacation rental in Sugarloaf Key
Pet friendly amazing location in paradise, vacation rental in Sugarloaf Key
Pet friendly amazing location in paradise, vacation rental in Sugarloaf Key

Pet friendly amazing location in paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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3 bedroom accommodation in Key West, vacation rental in Sugarloaf Key
3 bedroom accommodation in Key West, vacation rental in Sugarloaf Key
3 bedroom accommodation in Key West, vacation rental in Sugarloaf Key

3 bedroom accommodation in Key West

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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