Vacation rentals in Sugarloaf Key, FL

Best vacation rentals and Airbnb offers in Sugarloaf Key, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Sugarloaf Key

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

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About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Key, 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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Sugarloaf Key RV Resort & Cottages

Holiday Home, Sugarloaf Key

Sugarloaf Key RV Resort & Cottages is a holiday home in Sugarloaf Key, 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 Key, 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 $1,199.

From$171/night

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Cottage with swimming pool and dockage, just minutes to Key West!

Cottage, Sugarloaf Key

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

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About Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Sugarloaf Key, 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 $1,394.

From$199/night

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Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage, Sugarloaf Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Sugarloaf Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers…

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About Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Sugarloaf Key, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,460.

From$209/night

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Vacation rentals with a pool in Sugarloaf Key, FL

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

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Holiday Home, Sugarloaf Key

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon is a holiday home in Sugarloaf Key, with pool access and easy beach access. This stay gives travelers a…

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About Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon is a holiday home in Sugarloaf Key, 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 $1,670.

From$239/night

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Enjoy Caribbean weather in the USA. Openings June 2026 forward!

Holiday Home, Sugarloaf Key

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Sugarloaf Key, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Enjoy Caribbean weather in the USA. Openings June 2026 forward!

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Sugarloaf Key, 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 $1,754.

From$251/night

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Seas The Day in Cudjoe Key

Holiday Home, Sugarloaf Key

Seas The Day in Cudjoe Key is a holiday home in Sugarloaf Key, 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 Key, 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 $1,775.

From$254/night

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Ocean Breeze Retreat w/ Dock - Keys Escape

Holiday Home, Sugarloaf Key

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Sugarloaf Key, 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 Key, 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 $1,775.

From$254/night

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Vacation rentals with parking in Sugarloaf Key, FL

Find vacation rentals that make arriving by car easier.

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

Holiday Home, Sugarloaf Key

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

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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 Key, 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 $2,798.

From$400/night

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Starlight Serenity - Hideaway w Stunning Views

Holiday Home, Sugarloaf Key

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Sugarloaf Key, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Sugarloaf Key, with pet-friendly space 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 wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,527.

From$403/night

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101- Oceanside House with Pool

Holiday Home, Sugarloaf Key

101- Oceanside House with Pool is a holiday home in Sugarloaf Key, 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 Key, 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 $3,084.

From$441/night

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103- Newly Renovated House with Oceanview and Pool

Holiday Home, Sugarloaf Key

103- Newly Renovated House with Oceanview and Pool is a holiday home in Sugarloaf Key, 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 Key, 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 $3,097.

From$442/night

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Pet-friendly vacation rentals in Sugarloaf Key, FL

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

FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!

Cottage, Sugarloaf Key

FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED! is a cottage in Sugarloaf Key, with pet-friendly space, pool access, and room for a group. This stay gives travelers a…

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About FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!

FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED! is a cottage in Sugarloaf Key, 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 $1,715.

From$245/night

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Seascape Vacation!!!

Holiday Home, Sugarloaf Key

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

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About Seascape Vacation!!!

Seascape Vacation!!! is a holiday home in Sugarloaf Key, 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 $1,747.

From$250/night

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

Holiday Home, Sugarloaf Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Sugarloaf Key, 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 Key, 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 $1,770.

From$253/night

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Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Sugarloaf Key

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

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About Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Sugarloaf Key, 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 $2,419.

From$346/night

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Vacation rentals with a kitchen in Sugarloaf Key, FL

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

Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Sugarloaf Key

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

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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 Key, 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 $1,954.

From$279/night

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Sun Bake @ Sponge Cake, 64' Sea Wall,

Holiday Home, Sugarloaf Key

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

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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 Key, 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 $1,980.

From$283/night

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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cottage, Sugarloaf Key

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! is a cottage in Sugarloaf Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! is a cottage in Sugarloaf Key, 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 $2,088.

From$298/night

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Lower Keys paradise

Holiday Home, Sugarloaf Key

Lower Keys paradise is a holiday home in Sugarloaf Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Lower Keys paradise

Lower Keys paradise is a holiday home in Sugarloaf Key, 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 $2,097.

From$300/night

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Family-friendly vacation rentals in Sugarloaf Key, 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 Key

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Sugarloaf Key, 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 Key, 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 $1,414.

From$202/night

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A slice of paradise

Cottage, Sugarloaf Key

A slice of paradise is a cottage in Sugarloaf Key, 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 Key, 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 $1,919.

From$274/night

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Fishermen’s Paradise

Cottage, Sugarloaf Key

Fishermen’s Paradise is a cottage in Sugarloaf Key, 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 Fishermen’s Paradise

Fishermen’s Paradise is a cottage in Sugarloaf Key, 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 $1,998.

From$285/night

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Imagine in the Keys - Venture Out Unit 073

Cottage, Sugarloaf Key

Imagine in the Keys - Venture Out Unit 073 is a cottage in Sugarloaf Key, 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 Key, 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 $1,998.

From$285/night

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