Vacation rentals in Florida Keys, FL

Best vacation rentals and Airbnb offers in Florida Keys, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Florida Keys

Sugarloaf Key RV Resort & Cottages is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,210.

From$139/night

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Sugarloaf Key RV Resort & Cottages

Holiday Home, Florida Keys

Sugarloaf Key RV Resort & Cottages is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,199.

From$171/night

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

Holiday Home, Florida Keys

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

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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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,317.

From$188/night

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

Cottage, Florida Keys

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,394.

From$199/night

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Family-friendly vacation rentals in Florida Keys, FL

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

Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home, Florida Keys

Kelly's Kabin - Adorable Private Summerland Key Cottage is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,414.

From$202/night

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Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Holiday Home, Florida Keys

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access is a holiday home in Florida Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access is a holiday home in Florida Keys, with pet-friendly space, pool access, and outdoor space. 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,589.

From$227/night

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ISLE BE BACK To The Sunny Keys

Cottage, Florida Keys

ISLE BE BACK To The Sunny Keys is a cottage in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,614.

From$231/night

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Coconut Cottage #653 - Oceanfront Community

Holiday Home, Florida Keys

Coconut Cottage #653 - Oceanfront Community is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,627.

From$232/night

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Pet-friendly vacation rentals in Florida Keys, FL

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

Seascape Vacation!!!

Holiday Home, Florida Keys

Seascape Vacation!!! is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 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, Florida Keys

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,864.

From$266/night

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Canal front, dockage, 2 bedroom, 2 bath

Cottage, Florida Keys

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Florida Keys, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,224.

From$318/night

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Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Florida Keys

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,416.

From$345/night

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Vacation rentals with a pool in Florida Keys, 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, Florida Keys

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,670.

From$239/night

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

Holiday Home, Florida Keys

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 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, Florida Keys

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,754.

From$251/night

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Seas The Day in Cudjoe Key

Holiday Home, Florida Keys

Seas The Day in Cudjoe Key is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,775.

From$254/night

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Vacation rentals with parking in Florida Keys, FL

Find vacation rentals that make arriving by car easier.

Key West - Stock Island

Holiday Home, Florida Keys

Key West - Stock Island is a holiday home in Florida Keys, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Key West - Stock Island

Key West - Stock Island is a holiday home in Florida Keys, 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, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,083.

From$298/night

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

Holiday Home, Florida Keys

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,798.

From$400/night

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Starlight Serenity - Hideaway w Stunning Views

Holiday Home, Florida Keys

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,521.

From$402/night

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101- Oceanside House with Pool

Holiday Home, Florida Keys

101- Oceanside House with Pool is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,084.

From$441/night

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Vacation rentals with a kitchen in Florida Keys, FL

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

Ocean Breeze Retreat w/ Dock - Keys Escape

Holiday Home, Florida Keys

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,785.

From$255/night

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A slice of paradise

Cottage, Florida Keys

A slice of paradise is a cottage in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,919.

From$274/night

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Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Florida Keys

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,954.

From$279/night

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Sun Bake @ Sponge Cake, 64' Sea Wall,

Holiday Home, Florida Keys

Sun Bake @ Sponge Cake, 64' Sea Wall, is a holiday home in Florida Keys, 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 Florida Keys, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,980.

From$283/night

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