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Sugarloaf Key Holiday 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, holiday rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse, holiday rental in Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse, holiday rental in Sugarloaf Key

Bungalows at Sugarloaf Beach - The Lighthouse

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

Sugarloaf Key Home With Beach, Dock and Canal!

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

Fish Camp: Old-school Keys getaway

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront Studio-15 min to Key West, holiday rental in Sugarloaf Key
Beautiful Waterfront Studio-15 min to Key West, holiday rental in Sugarloaf Key
Beautiful Waterfront Studio-15 min to Key West, holiday 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, holiday rental in Sugarloaf Key
The Sunset Cottage of Pelico Palms, holiday rental in Sugarloaf Key
The Sunset Cottage of Pelico Palms, holiday rental in Sugarloaf Key

The Sunset Cottage of Pelico Palms

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

Waterfront Sugarloaf Key Home Open for Summer Months

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, holiday rental in Sugarloaf Key
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, holiday rental in Sugarloaf Key
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D, holiday rental in Sugarloaf Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Oceanfront quiet neighborhood with Dock, holiday rental in Sugarloaf Key
Beautiful Oceanfront quiet neighborhood with Dock, holiday rental in Sugarloaf Key
Beautiful Oceanfront quiet neighborhood with Dock, holiday rental in Sugarloaf Key

Beautiful Oceanfront quiet neighborhood with Dock

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Bungalow with Dockage, holiday rental in Sugarloaf Key
Waterfront Bungalow with Dockage, holiday rental in Sugarloaf Key
Waterfront Bungalow with Dockage, holiday rental in Sugarloaf Key

Waterfront Bungalow with Dockage

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

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

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

Oceanfront Paradise! (15 minutes from Duval)

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

Oceanfront Beach Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful quiet neighborhood. Sunsets! Huge Pool!, holiday rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge Pool!, holiday rental in Sugarloaf Key
Beautiful quiet neighborhood. Sunsets! Huge Pool!, holiday rental in Sugarloaf Key

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The oasis-waterfront house, holiday rental in Sugarloaf Key
The oasis-waterfront house, holiday rental in Sugarloaf Key
The oasis-waterfront house, holiday rental in Sugarloaf Key

The oasis-waterfront house

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

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

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

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

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

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

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

Bungalows at Sugarloaf Beach - Hammock House

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

Palms Resort - Guest House

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pet friendly amazing location in paradise, holiday rental in Sugarloaf Key
Pet friendly amazing location in paradise, holiday rental in Sugarloaf Key
Pet friendly amazing location in paradise, holiday rental in Sugarloaf Key

Pet friendly amazing location in paradise

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Bungalows at Sugarloaf Beach- The Hemingway, holiday rental in Sugarloaf Key
Bungalows at Sugarloaf Beach- The Hemingway, holiday rental in Sugarloaf Key
Bungalows at Sugarloaf Beach- The Hemingway, holiday rental in Sugarloaf Key

Bungalows at Sugarloaf Beach- The Hemingway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House with 2 balconies, deck with boat ramp, park nearby, holiday rental in Sugarloaf Key
House with 2 balconies, deck with boat ramp, park nearby, holiday rental in Sugarloaf Key
House with 2 balconies, deck with boat ramp, park nearby, holiday rental in Sugarloaf Key

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bayside Beauty on Open Water, holiday rental in Sugarloaf Key
Bayside Beauty on Open Water, holiday rental in Sugarloaf Key
Bayside Beauty on Open Water, holiday rental in Sugarloaf Key

Bayside Beauty on Open Water

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tranquility in Paradise - Sugarloaf, holiday rental in Sugarloaf Key
Tranquility in Paradise - Sugarloaf, holiday rental in Sugarloaf Key
Tranquility in Paradise - Sugarloaf, holiday rental in Sugarloaf Key

Tranquility in Paradise - Sugarloaf

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Affiliated with FlipKey
Rare opportunity 2023 Summer/Fall availability., holiday rental in Sugarloaf Key
Rare opportunity 2023 Summer/Fall availability., holiday rental in Sugarloaf Key
Rare opportunity 2023 Summer/Fall availability., holiday rental in Sugarloaf Key

Rare opportunity 2023 Summer/Fall availability.

Holiday Rental House
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, holiday rental in Sugarloaf Key
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di, holiday rental in Sugarloaf Key
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di, holiday rental in Sugarloaf Key

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

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

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
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, holiday rental in Sugarloaf Key
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

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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, holiday rental in Sugarloaf Key
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, holiday rental in Sugarloaf Key
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot, holiday rental in Sugarloaf Key

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Summer Sunsets are waiting for you !!, holiday rental in Sugarloaf Key
Summer Sunsets are waiting for you !!, holiday rental in Sugarloaf Key
Summer Sunsets are waiting for you !!, holiday rental in Sugarloaf Key

Summer Sunsets are waiting for you !!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Blue Wahoo-Perfect Keys Getaway, holiday rental in Sugarloaf Key
Blue Wahoo-Perfect Keys Getaway, holiday rental in Sugarloaf Key
Blue Wahoo-Perfect Keys Getaway, holiday rental in Sugarloaf Key

Blue Wahoo-Perfect Keys Getaway

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Villa of Pelico Palms, holiday rental in Sugarloaf Key
The Villa of Pelico Palms, holiday rental in Sugarloaf Key
The Villa of Pelico Palms, holiday rental in Sugarloaf Key

The Villa of Pelico Palms

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

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

Holiday Rental House
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, holiday rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag, holiday rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag, holiday rental in Sugarloaf Key

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, holiday rental in Sugarloaf Key
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, holiday rental in Sugarloaf Key
#SUGARFOOT_SUNSETS PRIVATEBEACH, BRINGBOAT, SERVICELIFT, HEATED SALT POOL TIKI, holiday rental in Sugarloaf Key

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

Holiday Rental House
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, holiday rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog, holiday rental in Sugarloaf Key
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dog, holiday rental in Sugarloaf Key

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

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

Family Friendly House In Paradise

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

Stunning Canal Front Pool Home

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

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

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

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

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

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

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

Key West Beach House with pool and dock , ♿︎

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cassie's Paradise, holiday rental in Sugarloaf Key
Cassie's Paradise, holiday rental in Sugarloaf Key
Cassie's Paradise, holiday rental in Sugarloaf Key

Cassie's Paradise

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Villa and Guest House of Pelico Palms, holiday rental in Sugarloaf Key
Villa and Guest House of Pelico Palms, holiday rental in Sugarloaf Key
Villa and Guest House of Pelico Palms, holiday rental in Sugarloaf Key

Villa and Guest House of Pelico Palms

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

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

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

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

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Pelico Palms Estate., holiday rental in Sugarloaf Key
Pelico Palms Estate., holiday rental in Sugarloaf Key
Pelico Palms Estate., holiday rental in Sugarloaf Key

Pelico Palms Estate.

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Waterfront Paradise at Ocean 18, holiday rental in Sugarloaf Key
Waterfront Paradise at Ocean 18, holiday rental in Sugarloaf Key
Waterfront Paradise at Ocean 18, holiday rental in Sugarloaf Key

Waterfront Paradise at Ocean 18

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V, holiday rental in Sugarloaf Key
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V, holiday rental in Sugarloaf Key
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V, holiday rental in Sugarloaf Key

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V

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