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Sugarloaf Key Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
53 rentals in Sugarloaf Key.
Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf Key

Bungalows at Sugarloaf Beach - The Lighthouse

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf Key
Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf Key
Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf Key

Sugarloaf Key Home With Beach, Dock and Canal!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Fish Camp: Old-school Keys getaway, vacation rental in Sugarloaf Key
Fish Camp: Old-school Keys getaway, vacation rental in Sugarloaf Key
Fish Camp: Old-school Keys getaway, vacation rental in Sugarloaf Key

Fish Camp: Old-school Keys getaway

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront Studio-15 min to Key West, vacation rental in Sugarloaf Key
Beautiful Waterfront Studio-15 min to Key West, vacation rental in Sugarloaf Key
Beautiful Waterfront Studio-15 min to Key West, vacation rental in Sugarloaf Key

Beautiful Waterfront Studio-15 min to Key West

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf Key
The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf Key
The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf Key

The Sunset Cottage of Pelico Palms

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Sugarloaf Key Home Open for Summer Months, vacation rental in Sugarloaf Key
Waterfront Sugarloaf Key Home Open for Summer Months, vacation rental in Sugarloaf Key
Waterfront Sugarloaf Key Home Open for Summer Months, vacation rental in Sugarloaf Key

Waterfront Sugarloaf Key Home Open for Summer Months

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, vacation rental in Sugarloaf Key
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, vacation rental in Sugarloaf Key
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, vacation rental in Sugarloaf Key

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Oceanfront quiet neighborhood with Dock, vacation rental in Sugarloaf Key
Beautiful Oceanfront quiet neighborhood with Dock, vacation rental in Sugarloaf Key
Beautiful Oceanfront quiet neighborhood with Dock, vacation rental in Sugarloaf Key

Beautiful Oceanfront quiet neighborhood with Dock

Rental Home
1 bedroom
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Bungalow with Dockage, vacation rental in Sugarloaf Key
Waterfront Bungalow with Dockage, vacation rental in Sugarloaf Key
Waterfront Bungalow with Dockage, vacation rental in Sugarloaf Key

Waterfront Bungalow with Dockage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Serenity In Sugarloaf - 2BR Waterfront, Pool, Tiki, Dock, vacation rental in Sugarloaf Key
Tropical Serenity In Sugarloaf - 2BR Waterfront, Pool, Tiki, Dock, vacation rental in Sugarloaf Key
Tropical Serenity In Sugarloaf - 2BR Waterfront, Pool, Tiki, Dock, vacation rental in Sugarloaf Key

Tropical Serenity In Sugarloaf - 2BR Waterfront, Pool, Tiki, Dock

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Paradise! (15 minutes from Duval), vacation rental in Sugarloaf Key
Oceanfront Paradise! (15 minutes from Duval), vacation rental in Sugarloaf Key
Oceanfront Paradise! (15 minutes from Duval), vacation rental in Sugarloaf Key

Oceanfront Paradise! (15 minutes from Duval)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Beach Home, vacation rental in Sugarloaf Key
Oceanfront Beach Home, vacation rental in Sugarloaf Key
Oceanfront Beach Home, vacation rental in Sugarloaf Key

Oceanfront Beach Home

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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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Waterfront 2 bedroom oasis close to Key West, vacation rental in Sugarloaf Key
Waterfront 2 bedroom oasis close to Key West, vacation rental in Sugarloaf Key
Waterfront 2 bedroom oasis close to Key West, vacation rental in Sugarloaf Key

Waterfront 2 bedroom oasis close to Key West

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The oasis-waterfront house, vacation rental in Sugarloaf Key
The oasis-waterfront house, vacation rental in Sugarloaf Key
The oasis-waterfront house, vacation rental in Sugarloaf Key

The oasis-waterfront house

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 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
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!, vacation rental in Sugarloaf Key
Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!, vacation rental in Sugarloaf Key
Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!, vacation rental in Sugarloaf Key

Your own Private Resort! 50ft Dock on Canal w/ Pool and RV Hookup!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New-build, luxury canal front home w/ dock, firepit, micro pool, vacation rental in Sugarloaf Key
New-build, luxury canal front home w/ dock, firepit, micro pool, vacation rental in Sugarloaf Key
New-build, luxury canal front home w/ dock, firepit, micro pool, vacation rental in Sugarloaf Key

New-build, luxury canal front home w/ dock, firepit, micro pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf Key

Bungalows at Sugarloaf Beach - Hammock House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Palms Resort  - Guest House, vacation rental in Sugarloaf Key
Palms Resort  - Guest House, vacation rental in Sugarloaf Key
Palms Resort  - Guest House, vacation rental in Sugarloaf Key

Palms Resort - Guest House

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
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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Bungalows at Sugarloaf Beach- The Hemingway, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach- The Hemingway, vacation rental in Sugarloaf Key
Bungalows at Sugarloaf Beach- The Hemingway, vacation rental in Sugarloaf Key

Bungalows at Sugarloaf Beach- The Hemingway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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House with 2 balconies, deck with boat ramp, park nearby, vacation rental in Sugarloaf Key
House with 2 balconies, deck with boat ramp, park nearby, vacation rental in Sugarloaf Key
House with 2 balconies, deck with boat ramp, park nearby, vacation rental in Sugarloaf Key

House with 2 balconies, deck with boat ramp, park nearby

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bayside Beauty on Open Water, vacation rental in Sugarloaf Key
Bayside Beauty on Open Water, vacation rental in Sugarloaf Key
Bayside Beauty on Open Water, vacation rental in Sugarloaf Key

Bayside Beauty on Open Water

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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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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Rare opportunity 2023 Summer/Fall availability., vacation rental in Sugarloaf Key
Rare opportunity 2023 Summer/Fall availability., vacation rental in Sugarloaf Key
Rare opportunity 2023 Summer/Fall availability., vacation rental in Sugarloaf Key

Rare opportunity 2023 Summer/Fall availability.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di, vacation rental in Sugarloaf Key
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di, vacation rental in Sugarloaf Key
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di, vacation rental in Sugarloaf Key

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Summer get away desination- at the newly renovated three story fun house!, vacation rental in Sugarloaf Key
Summer get away desination- at the newly renovated three story fun house!, vacation rental in Sugarloaf Key
Summer get away desination- at the newly renovated three story fun house!, vacation rental in Sugarloaf Key

Summer get away desination- at the newly renovated three story fun house!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West, vacation rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West, vacation rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West, vacation rental in Sugarloaf Key

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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For up to date Information call *******-5000, vacation rental in Sugarloaf Key
For up to date Information call *******-5000, vacation rental in Sugarloaf Key
For up to date Information call *******-5000, vacation rental in Sugarloaf Key

For up to date Information call *******-5000

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, vacation rental in Sugarloaf Key
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, vacation rental in Sugarloaf Key
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, vacation rental in Sugarloaf Key

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf Key
Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf Key
Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf Key

Summer Sunsets are waiting for you !!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf Key
Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf Key
Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf Key

Blue Wahoo-Perfect Keys Getaway

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Villa of Pelico Palms, vacation rental in Sugarloaf Key
The Villa of Pelico Palms, vacation rental in Sugarloaf Key
The Villa of Pelico Palms, vacation rental in Sugarloaf Key

The Villa of Pelico Palms

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly, vacation rental in Sugarloaf Key
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly, vacation rental in Sugarloaf Key
Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly, vacation rental in Sugarloaf Key

Stunning, Oceanfront Home with Private Pool & Docks - Dog-Friendly

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag, vacation rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag, vacation rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag, vacation rental in Sugarloaf Key

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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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Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog, vacation rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog, vacation rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog, vacation rental in Sugarloaf Key

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly House In Paradise, vacation rental in Sugarloaf Key
Family Friendly House In Paradise, vacation rental in Sugarloaf Key
Family Friendly House In Paradise, vacation rental in Sugarloaf Key

Family Friendly House In Paradise

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Canal Front Pool Home, vacation rental in Sugarloaf Key
Stunning Canal Front Pool Home, vacation rental in Sugarloaf Key
Stunning Canal Front Pool Home, vacation rental in Sugarloaf Key

Stunning Canal Front Pool Home

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key
**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key
**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key

**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Oceanfront Home w/ a Private Pool, High-Speed WiFi, & Private Beach, vacation rental in Sugarloaf Key
Luxurious Oceanfront Home w/ a Private Pool, High-Speed WiFi, & Private Beach, vacation rental in Sugarloaf Key
Luxurious Oceanfront Home w/ a Private Pool, High-Speed WiFi, & Private Beach, vacation rental in Sugarloaf Key

Luxurious Oceanfront Home w/ a Private Pool, High-Speed WiFi, & Private Beach

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Oceanfront 5BR Property with heated Pool & Waterfall, vacation rental in Sugarloaf Key
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall, vacation rental in Sugarloaf Key
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall, vacation rental in Sugarloaf Key

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Key West Beach House with pool and dock ,  ♿︎, vacation rental in Sugarloaf Key
Key West Beach House with pool and dock ,  ♿︎, vacation rental in Sugarloaf Key
Key West Beach House with pool and dock ,  ♿︎, vacation rental in Sugarloaf Key

Key West Beach House with pool and dock , ♿︎

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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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Villa and Guest House of Pelico Palms, vacation rental in Sugarloaf Key
Villa and Guest House of Pelico Palms, vacation rental in Sugarloaf Key
Villa and Guest House of Pelico Palms, vacation rental in Sugarloaf Key

Villa and Guest House of Pelico Palms

Rental Home
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Ocean9 Villa, amazing waterfront, 15 min away from Duval Street!, vacation rental in Sugarloaf Key
Ocean9 Villa, amazing waterfront, 15 min away from Duval Street!, vacation rental in Sugarloaf Key
Ocean9 Villa, amazing waterfront, 15 min away from Duval Street!, vacation rental in Sugarloaf Key

Ocean9 Villa, amazing waterfront, 15 min away from Duval Street!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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**PLAYLAND IN PARADISE * BAY POINT** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key
**PLAYLAND IN PARADISE * BAY POINT** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key
**PLAYLAND IN PARADISE * BAY POINT** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf Key

**PLAYLAND IN PARADISE * BAY POINT** Waterfront Home & Pool + LAST KEY SERVICES…

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Pelico Palms Estate., vacation rental in Sugarloaf Key
Pelico Palms Estate., vacation rental in Sugarloaf Key
Pelico Palms Estate., vacation rental in Sugarloaf Key

Pelico Palms Estate.

Rental Home
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Waterfront Paradise at Ocean 18, vacation rental in Sugarloaf Key
Waterfront Paradise at Ocean 18, vacation rental in Sugarloaf Key
Waterfront Paradise at Ocean 18, vacation rental in Sugarloaf Key

Waterfront Paradise at Ocean 18

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 53
Frequently Asked Questions about Sugarloaf Key