Vacation rentals in Summerland Key, FL

Best vacation rentals and Airbnb offers in Summerland Key, FL

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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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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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 $1,769.

From$253/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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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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Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Summerland Key

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

From$346/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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101- Oceanside House with Pool

Holiday Home, Summerland Key

101- Oceanside House with Pool is a holiday home in Summerland 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 Summerland 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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Pet-friendly vacation rentals in Summerland Key, FL

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

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

Cottage, Summerland Key

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

Quaint cottage, pool, 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 $1,660.

From$237/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 $1,770.

From$253/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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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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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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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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