Vacation rentals in Sugarloaf Shores, FL

Best Vacation rentals and Airbnb offers in Sugarloaf Shores, FL

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Holiday Home, Sugarloaf Shores

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and room for a group. This stay gives…

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About JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,470.

From$84/night

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Sugarloaf Key RV Resort & Cottages

Holiday Home, Sugarloaf Shores

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Shores, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Shores, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,210.

From$139/night

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ISLE BE BACK To The Sunny Keys

Cottage, Sugarloaf Shores

ISLE BE BACK To The Sunny Keys is a cottage in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About ISLE BE BACK To The Sunny Keys

ISLE BE BACK To The Sunny Keys is a cottage in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,750.

From$148/night

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Sugarloaf Key RV Resort & Cottages

Holiday Home, Sugarloaf Shores

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

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About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$155/night

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Browse Vacation Rentals with a Pool in Sugarloaf Shores, FL

Add a pool to the search when you want an easy place to cool off between outings.

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Holiday Home, Sugarloaf Shores

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key is a holiday home in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key is a holiday home in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,911.

From$179/night

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Seas The Day in Cudjoe Key

Holiday Home, Sugarloaf Shores

Seas The Day in Cudjoe Key is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Seas The Day in Cudjoe Key

Seas The Day in Cudjoe Key is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,976.

From$180/night

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Imagine in the Keys - Venture Out Unit 073

Cottage, Sugarloaf Shores

Imagine in the Keys - Venture Out Unit 073 is a cottage in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Imagine in the Keys - Venture Out Unit 073

Imagine in the Keys - Venture Out Unit 073 is a cottage in Sugarloaf Shores, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,173.

From$200/night

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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage, Sugarloaf Shores

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West is a cottage in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a…

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About Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West is a cottage in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,977.

From$208/night

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Best Sugarloaf Shores, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

Holiday Home, Sugarloaf Shores

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Sugarloaf Shores, with pool access, parking, and kitchen access. This stay gives travelers…

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About Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Sugarloaf Shores, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,104.

From$311/night

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101- Oceanside House with Pool

Holiday Home, Sugarloaf Shores

101- Oceanside House with Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 101- Oceanside House with Pool

101- Oceanside House with Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,366.

From$322/night

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103- Newly Renovated House with Oceanview and Pool

Holiday Home, Sugarloaf Shores

103- Newly Renovated House with Oceanview and Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About 103- Newly Renovated House with Oceanview and Pool

103- Newly Renovated House with Oceanview and Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,381.

From$324/night

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102 - Newly renovated house Oceanside and Pool

Holiday Home, Sugarloaf Shores

102 - Newly renovated house Oceanside and Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About 102 - Newly renovated house Oceanside and Pool

102 - Newly renovated house Oceanside and Pool is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,466.

From$332/night

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Best Pet-Friendly Vacation Rentals in Sugarloaf Shores, FL

Bring your pet along with stays that welcome four-legged travelers.

Seascape Vacation!!!

Holiday Home, Sugarloaf Shores

Seascape Vacation!!! is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Seascape Vacation!!!

Seascape Vacation!!! is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,942.

From$173/night

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Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Holiday Home, Sugarloaf Shores

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,065.

From$194/night

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Venture Out Million Dollar Ocean View

Holiday Home, Sugarloaf Shores

Venture Out Million Dollar Ocean View is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

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About Venture Out Million Dollar Ocean View

Venture Out Million Dollar Ocean View is a holiday home in Sugarloaf Shores, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,085.

From$259/night

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Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Sugarloaf Shores

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Sugarloaf Shores, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Sugarloaf Shores, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,686.

From$267/night

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Best Sugarloaf Shores, FL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Ocean Breeze Retreat w/ Dock - Keys Escape

Holiday Home, Sugarloaf Shores

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Ocean Breeze Retreat w/ Dock - Keys Escape

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,021.

From$209/night

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A slice of paradise

Cottage, Sugarloaf Shores

A slice of paradise is a cottage in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About A slice of paradise

A slice of paradise is a cottage in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,130.

From$220/night

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Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Sugarloaf Shores

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Pelican's Roost, Waterfront comfort at Venture Out

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Sugarloaf Shores, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,172.

From$228/night

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Sun Bake @ Sponge Cake, 64' Sea Wall,

Holiday Home, Sugarloaf Shores

Sun Bake @ Sponge Cake, 64' Sea Wall, is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sun Bake @ Sponge Cake, 64' Sea Wall,

Sun Bake @ Sponge Cake, 64' Sea Wall, is a holiday home in Sugarloaf Shores, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,198.

From$228/night

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Our Favorite Family-Friendly Vacation Rentals in Sugarloaf Shores, FL

Plan a trip with stays that give families more room to spread out.

Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home, Sugarloaf Shores

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Sugarloaf Shores, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Sugarloaf Shores, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,572.

From$151/night

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Coconut Cottage #653 - Oceanfront Community

Holiday Home, Sugarloaf Shores

Coconut Cottage #653 - Oceanfront Community is a holiday home in Sugarloaf Shores, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the…

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About Coconut Cottage #653 - Oceanfront Community

Coconut Cottage #653 - Oceanfront Community is a holiday home in Sugarloaf Shores, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,808.

From$175/night

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Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Cottage, Sugarloaf Shores

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West. is a cottage in Sugarloaf Shores, with pool access, outdoor space, and kitchen access. This stay gives travelers a…

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About Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West. is a cottage in Sugarloaf Shores, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,758.

From$182/night

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Quaint cottage, pool, dockage just minutes to Key West!

Cottage, Sugarloaf Shores

Quaint cottage, pool, dockage just minutes to Key West! is a cottage in Sugarloaf Shores, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West! is a cottage in Sugarloaf Shores, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,843.

From$195/night

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