Vacation rentals in Summerland Key, FL

Best vacation rentals and Airbnb offers in Summerland Key, FL

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

Holiday Home, Summerland Key

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! is a holiday home in Summerland Key, 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 Summerland 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 $1,317.

From$188/night

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Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home, Summerland Key

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Summerland 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 Summerland 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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SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster

Cottage, Summerland Key

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster is a cottage in Summerland Key, with pet-friendly space and pool access. This stay gives travelers a…

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About SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster is a cottage in Summerland 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 $1,417.

From$202/night

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Island Home in Paradise #624 - OCEANFRONT Community!

Holiday Home, Summerland Key

Island Home in Paradise #624 - OCEANFRONT Community! is a holiday home in Summerland Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring…

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About Island Home in Paradise #624 - OCEANFRONT Community!

Island Home in Paradise #624 - OCEANFRONT Community! is a holiday home in Summerland 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 $1,551.

From$222/night

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Vacation rentals with a pool in Summerland Key, 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, Summerland Key

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

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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 Summerland 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 $1,719.

From$246/night

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

Holiday Home, Summerland Key

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Summerland 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 Summerland 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, Summerland Key

Seas The Day in Cudjoe Key is a holiday home in Summerland 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 Summerland 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, Summerland Key

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Summerland 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 Summerland 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 $1,800.

From$257/night

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Vacation rentals with parking in Summerland Key, FL

Find vacation rentals that make arriving by car easier.

Sugarloaf Key RV Resort & Cottages

Holiday Home, Summerland Key

Sugarloaf Key RV Resort & Cottages is a holiday home in Summerland 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 Summerland 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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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage, Summerland Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West is a cottage in Summerland Key, with pool access, parking, 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 Summerland 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,518.

From$217/night

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Our little slice of paradise

Holiday Home, Summerland Key

Our little slice of paradise is a holiday home in Summerland Key, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Our little slice of paradise

Our little slice of paradise is a holiday home in Summerland 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 $2,257.

From$322/night

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

Holiday Home, Summerland Key

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Summerland 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 Summerland 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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Pet-friendly vacation rentals in Summerland Key, FL

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

Direct Oceanfront Cottage-Sunrise View- #2,

Cottage, Summerland Key

Direct Oceanfront Cottage-Sunrise View- #2, is a cottage in Summerland Key, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2, is a cottage in Summerland Key, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,495.

From$214/night

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Cottage with Pool and Dockage, just minutes to Key West

Cottage, Summerland Key

Cottage with Pool and Dockage, just minutes to Key West is a cottage in Summerland Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West is a cottage in Summerland 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 $1,501.

From$214/night

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Seascape Vacation!!!

Holiday Home, Summerland Key

Seascape Vacation!!! is a holiday home in Summerland 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 Summerland 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, Summerland Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Summerland 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 Summerland 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 $1,861.

From$266/night

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Vacation rentals with a kitchen in Summerland Key, FL

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

A slice of paradise

Cottage, Summerland Key

A slice of paradise is a cottage in Summerland 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 Summerland 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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Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Summerland Key

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Summerland 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 Summerland 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, Summerland Key

Sun Bake @ Sponge Cake, 64' Sea Wall, is a holiday home in Summerland 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 Summerland 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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Fishermen’s Paradise

Cottage, Summerland Key

Fishermen’s Paradise is a cottage in Summerland 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 Summerland 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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Family-friendly vacation rentals in Summerland Key, FL

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

Sugarloaf Key RV Resort & Cottages

Holiday Home, Summerland Key

Sugarloaf Key RV Resort & Cottages is a holiday home in Summerland Key, 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 Summerland 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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Cottage with swimming pool and dockage, just minutes to Key West!

Cottage, Summerland Key

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Summerland 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 Summerland 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, Summerland Key

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

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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 Summerland 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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Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage, Summerland Key

Cottage with Pool and Boat Dockage just minutes to Key West! is a cottage in Summerland Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West! is a cottage in Summerland Key, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,473.

From$210/night

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