Vacation rentals in Cudjoe Bay, FL

130 available vacation rental offers

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Best vacation rentals and Airbnb offers in Cudjoe Bay, FL

Sugarloaf Key RV Resort & Cottages - Cudjoe Bay, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Cudjoe Bay

Sugarloaf Key RV Resort & Cottages is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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 - Cudjoe Bay, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Cudjoe Bay

Sugarloaf Key RV Resort & Cottages is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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! - Cudjoe Bay, FL

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

Holiday Home, Cudjoe Bay

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

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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 Cudjoe Bay, 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! - Cudjoe Bay, FL

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

Cottage, Cudjoe Bay

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Cudjoe Bay, 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 Cudjoe Bay, 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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Waterfront vacation rentals in Cudjoe Bay, FL

Discover vacation rentals close to the coast, water, and beach areas around Cudjoe Bay, FL.

Ocean Breeze Retreat w/ Dock - Keys Escape - Cudjoe Bay, FL

Ocean Breeze Retreat w/ Dock - Keys Escape

Holiday Home, Cudjoe Bay

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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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Pelican's Roost, Waterfront comfort at Venture Out - Cudjoe Bay, FL

Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Cudjoe Bay

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Cudjoe Bay, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the…

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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 Cudjoe Bay, 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: free cancellation, pool, hot tub, and free wifi.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,232.

From$262/night
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Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing - Cudjoe Bay, FL

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

Holiday Home, Cudjoe Bay

Waterfront 1BR in Venture Out with 35' Dock, Kayaks, Pool & World-Class Fishing is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,865.

From$266/night
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Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors - Cudjoe Bay, FL

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Holiday Home, Cudjoe Bay

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors is a holiday home in Cudjoe Bay, with pool access and easy beach access. This stay gives travelers a…

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About Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors is a holiday home in Cudjoe Bay, 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 $1,914.

From$273/night
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Family-friendly vacation rentals in Cudjoe Bay, FL

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

Kelly's Kabin - Adorable Private Summerland Key Cottage - Cudjoe Bay, FL

Kelly's Kabin - Adorable Private Summerland Key Cottage

Holiday Home, Cudjoe Bay

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

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

Cottage, Cudjoe Bay

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

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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 Cudjoe Bay, 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 $1,417.

From$202/night
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Quaint cottage, pool, dockage just minutes to Key West! - Cudjoe Bay, FL

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

Cottage, Cudjoe Bay

Quaint cottage, pool, dockage just minutes to Key West! is a cottage in Cudjoe Bay, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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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 Cudjoe Bay, 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 $1,660.

From$237/night
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West - Cudjoe Bay, FL

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage, Cudjoe Bay

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West is a cottage in Cudjoe Bay, with pool access and kitchen access. This stay gives travelers a comfortable base…

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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 Cudjoe Bay, 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, free wifi, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,662.

From$237/night
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Pet-friendly vacation rentals in Cudjoe Bay, FL

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

FLAMINGO COTTAGE sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED! - Cudjoe Bay, FL

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

Cottage, Cudjoe Bay

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

From$245/night
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Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season. - Cudjoe Bay, FL

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

Cottage, Cudjoe Bay

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

From$246/night
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Seascape Vacation!!! - Cudjoe Bay, FL

Seascape Vacation!!!

Holiday Home, Cudjoe Bay

Seascape Vacation!!! is a holiday home in Cudjoe Bay, 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 Seascape Vacation!!!

Seascape Vacation!!! is a holiday home in Cudjoe Bay, 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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Canal front, dockage, 2 bedroom, 2 bath - Cudjoe Bay, FL

Canal front, dockage, 2 bedroom, 2 bath

Cottage, Cudjoe Bay

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Cudjoe Bay, 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 Cudjoe Bay, 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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Vacation rentals with a pool in Cudjoe Bay, 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 - Cudjoe Bay, FL

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

Holiday Home, Cudjoe Bay

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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! - Cudjoe Bay, FL

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

Holiday Home, Cudjoe Bay

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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 - Cudjoe Bay, FL

Seas The Day in Cudjoe Key

Holiday Home, Cudjoe Bay

Seas The Day in Cudjoe Key is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West - Cudjoe Bay, FL

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage, Cudjoe Bay

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West is a cottage in Cudjoe Bay, with pool access and kitchen access. This stay gives travelers a comfortable base…

Read more

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 Cudjoe Bay, 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, free wifi, kitchen, and with kitchen.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,781.

From$254/night
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Vacation rentals with parking in Cudjoe Bay, FL

Find vacation rentals that make arriving by car easier.

Our little slice of paradise - Cudjoe Bay, FL

Our little slice of paradise

Holiday Home, Cudjoe Bay

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

From$322/night
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Starlight Serenity - Hideaway with Stunning Views - Cudjoe Bay, FL

Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Cudjoe Bay

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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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Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking - Cudjoe Bay, FL

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

Holiday Home, Cudjoe Bay

Open Water View from porch , golf cart, dock, bikes, kayaks, trailer parking is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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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101- Oceanside House with Pool - Cudjoe Bay, FL

101- Oceanside House with Pool

Holiday Home, Cudjoe Bay

101- Oceanside House with Pool is a holiday home in Cudjoe Bay, 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 Cudjoe Bay, 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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