Vacation rentals in Pirates Cove, FL

Best vacation rentals and Airbnb offers in Pirates Cove, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Pirates Cove

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

Sugarloaf Key RV Resort & Cottages is a holiday home in Pirates Cove, with pet-friendly space, pool access, and parking. 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 Pirates Cove, 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, Pirates Cove

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

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Pirates Cove, 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 Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key is a holiday home in Pirates Cove, 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 Pirates Cove, 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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Seas The Day in Cudjoe Key

Holiday Home, Pirates Cove

Seas The Day in Cudjoe Key is a holiday home in Pirates Cove, 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 Pirates Cove, 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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Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing

Holiday Home, Pirates Cove

Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing is a holiday home in Pirates Cove, with pool access, easy beach access, and room for a group. This stay gives…

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About Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing

Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing is a holiday home in Pirates Cove, with pool access, easy beach 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,865.

From$266/night

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Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Holiday Home, Pirates Cove

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option is a holiday home in Pirates Cove, with pool access, easy beach access, and a quieter setting. This stay gives travelers a…

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About Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option is a holiday home in Pirates Cove, with pool access, easy beach access, and a quieter setting. 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 $1,918.

From$274/night

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Vacation rentals with parking in Pirates Cove, FL

Find vacation rentals that make arriving by car easier.

Our little slice of paradise

Holiday Home, Pirates Cove

Our little slice of paradise is a holiday home in Pirates Cove, 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 Pirates Cove, 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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Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Pirates Cove

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Pirates Cove, 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 Pirates Cove, 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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Pet-friendly vacation rentals in Pirates Cove, FL

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

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

Cottage, Pirates Cove

FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED! is a cottage in Pirates Cove, 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 Pirates Cove, 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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Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season.

Cottage, Pirates Cove

Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season. is a cottage in Pirates Cove, with pet-friendly space, pool access, and room for a group. This stay gives…

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About Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season.

Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season. is a cottage in Pirates Cove, 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 $1,723.

From$246/night

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Seascape Vacation!!!

Holiday Home, Pirates Cove

Seascape Vacation!!! is a holiday home in Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Pirates Cove, 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 Pirates Cove, 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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Vacation rentals with a kitchen in Pirates Cove, FL

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

A slice of paradise

Cottage, Pirates Cove

A slice of paradise is a cottage in Pirates Cove, 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 Pirates Cove, 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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Sun Bake @ Sponge Cake, 64' Sea Wall,

Holiday Home, Pirates Cove

Sun Bake @ Sponge Cake, 64' Sea Wall, is a holiday home in Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

Fishermen’s Paradise is a cottage in Pirates Cove, 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 Pirates Cove, 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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Lower Keys paradise

Holiday Home, Pirates Cove

Lower Keys paradise is a holiday home in Pirates Cove, 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 Pirates Cove, 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 Pirates Cove, FL

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

Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home, Pirates Cove

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Pirates Cove, 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 Pirates Cove, 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, Pirates Cove

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster is a cottage in Pirates Cove, 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 Pirates Cove, 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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ISLE BE BACK To The Sunny Keys

Cottage, Pirates Cove

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

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About ISLE BE BACK To The Sunny Keys

ISLE BE BACK To The Sunny Keys is a cottage in Pirates Cove, 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 $1,614.

From$231/night

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Coconut Cottage #653 - Oceanfront Community

Holiday Home, Pirates Cove

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

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About Coconut Cottage #653 - Oceanfront Community

Coconut Cottage #653 - Oceanfront Community is a holiday home in Pirates Cove, 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 $1,627.

From$232/night

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