Vacation rentals in Raccoon Key, FL

52 available vacation rental offers

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Best vacation rentals and Airbnb offers in Raccoon Key, FL

Sugarloaf Key RV Resort & Cottages - Raccoon Key, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Raccoon Key

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

Sugarloaf Key RV Resort & Cottages

Holiday Home, Raccoon Key

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

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

Cottage, Raccoon Key

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Raccoon 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 Raccoon 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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SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster - Raccoon Key, FL

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

Cottage, Raccoon Key

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster is a cottage in Raccoon Key, 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 Raccoon 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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Vacation rentals with a pool in Raccoon Key, FL

Add a pool to the search when you want an easy place to cool off between outings.

Island Retreat w/ Private Patio & Marina Views | Breakfast Included - Raccoon Key, FL

Island Retreat w/ Private Patio & Marina Views | Breakfast Included

Holiday Home, Raccoon Key

Island Retreat w/ Private Patio & Marina Views · Breakfast Included is a holiday home in Raccoon Key, with pool access, outdoor space, and kitchen access. This stay gives travelers a…

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About Island Retreat w/ Private Patio & Marina Views | Breakfast Included

Island Retreat w/ Private Patio & Marina Views · Breakfast Included is a holiday home in Raccoon Key, with pool access, outdoor 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,263.

From$323/night
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New Construction in Venture Out! 3 night minimum stay. - Raccoon Key, FL

New Construction in Venture Out! 3 night minimum stay.

Holiday Home, Raccoon Key

New Construction in Venture Out! 3 night minimum stay. is a holiday home in Raccoon Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About New Construction in Venture Out! 3 night minimum stay.

New Construction in Venture Out! 3 night minimum stay. is a holiday home in Raccoon 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: free cancellation, pool, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,664.

From$381/night
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\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108 - Raccoon Key, FL

\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108

Holiday Home, Raccoon Key

\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108 is a holiday home in Raccoon Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About \"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108

\"WEEKLY RENTAL\" Florida Keys Pool & Waterfront Vacation Rental 108 is a holiday home in Raccoon 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,667.

From$381/night
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Shangri-la in the Keys! Enjoy the water views and a 45' dock space! - Raccoon Key, FL

Shangri-la in the Keys! Enjoy the water views and a 45' dock space!

Holiday Home, Raccoon Key

Shangri-la in the Keys! Enjoy the water views and a 45' dock space! is a holiday home in Raccoon Key, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Shangri-la in the Keys! Enjoy the water views and a 45' dock space!

Shangri-la in the Keys! Enjoy the water views and a 45' dock space! is a holiday home in Raccoon 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 $2,962.

From$423/night
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Vacation rentals with parking in Raccoon Key, FL

Find vacation rentals that make arriving by car easier.

Starlight Serenity - Hideaway w Stunning Views - Raccoon Key, FL

Starlight Serenity - Hideaway w Stunning Views

Holiday Home, Raccoon Key

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Raccoon Key, 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 Raccoon Key, 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 $3,521.

From$402/night
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101- Oceanside House with Pool - Raccoon Key, FL

101- Oceanside House with Pool

Holiday Home, Raccoon Key

101- Oceanside House with Pool is a holiday home in Raccoon 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 Raccoon 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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103- Newly Renovated House with Oceanview and Pool - Raccoon Key, FL

103- Newly Renovated House with Oceanview and Pool

Holiday Home, Raccoon Key

103- Newly Renovated House with Oceanview and Pool is a holiday home in Raccoon Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About 103- Newly Renovated House with Oceanview and Pool

103- Newly Renovated House with Oceanview and Pool is a holiday home in Raccoon 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 $3,097.

From$442/night
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102 - Newly renovated house Oceanside and Pool - Raccoon Key, FL

102 - Newly renovated house Oceanside and Pool

Holiday Home, Raccoon Key

102 - Newly renovated house Oceanside and Pool is a holiday home in Raccoon Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About 102 - Newly renovated house Oceanside and Pool

102 - Newly renovated house Oceanside and Pool is a holiday home in Raccoon 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 $3,175.

From$454/night
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Pet-friendly vacation rentals in Raccoon Key, FL

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

Our little slice of paradise - Raccoon Key, FL

Our little slice of paradise

Holiday Home, Raccoon Key

Our little slice of paradise is a holiday home in Raccoon 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 Raccoon 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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Starlight Serenity - Hideaway with Stunning Views - Raccoon Key, FL

Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Raccoon Key

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Raccoon Key, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Raccoon 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 $2,416.

From$345/night
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Just 20 miles from Key West! Oceanfront, dockage, swimming pool - Raccoon Key, FL

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Holiday Home, Raccoon Key

Just 20 miles from Key West! Oceanfront, dockage, swimming pool is a holiday home in Raccoon Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool is a holiday home in Raccoon 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 $2,427.

From$347/night
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Cudjoe Cottages, swimming pool, just 20 miles from Key West - Raccoon Key, FL

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Holiday Home, Raccoon Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West is a holiday home in Raccoon Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West is a holiday home in Raccoon 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 $2,547.

From$364/night
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Vacation rentals with a kitchen in Raccoon Key, FL

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West - Raccoon Key, FL

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Holiday Home, Raccoon Key

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West is a holiday home in Raccoon Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West is a holiday home in Raccoon 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,027.

From$432/night
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Oceanside home, dock,kayaks,bikes,pool,fishing,107 - Raccoon Key, FL

Oceanside home, dock,kayaks,bikes,pool,fishing,107

Holiday Home, Raccoon Key

Oceanside home, dock,kayaks,bikes,pool,fishing,107 is a holiday home in Raccoon Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Oceanside home, dock,kayaks,bikes,pool,fishing,107

Oceanside home, dock,kayaks,bikes,pool,fishing,107 is a holiday home in Raccoon 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 $3,038.

From$434/night
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Oceanside home, dock,kayaks,bikes,pool,fishing,109 - Raccoon Key, FL

Oceanside home, dock,kayaks,bikes,pool,fishing,109

Holiday Home, Raccoon Key

Oceanside home, dock,kayaks,bikes,pool,fishing,109 is a holiday home in Raccoon Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Oceanside home, dock,kayaks,bikes,pool,fishing,109

Oceanside home, dock,kayaks,bikes,pool,fishing,109 is a holiday home in Raccoon 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 $3,195.

From$456/night
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106- Newly Renovated House with Oceanview and Pool - Raccoon Key, FL

106- Newly Renovated House with Oceanview and Pool

Holiday Home, Raccoon Key

106- Newly Renovated House with Oceanview and Pool is a holiday home in Raccoon Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About 106- Newly Renovated House with Oceanview and Pool

106- Newly Renovated House with Oceanview and Pool is a holiday home in Raccoon 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 $3,292.

From$470/night
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Family-friendly vacation rentals in Raccoon Key, FL

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

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

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

Cottage, Raccoon Key

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

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

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

Cottage, Raccoon Key

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

From$246/night
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PALM COTTAGE - Sleeps 4 summer fun ..lobster season. - Raccoon Key, FL

PALM COTTAGE - Sleeps 4 summer fun ..lobster season.

Cottage, Raccoon Key

PALM COTTAGE - Sleeps 4 summer fun ..lobster season. is a cottage in Raccoon Key, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base…

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About PALM COTTAGE - Sleeps 4 summer fun ..lobster season.

PALM COTTAGE - Sleeps 4 summer fun ..lobster season. is a cottage in Raccoon 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 $1,864.

From$266/night
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Canal front, dockage, 2 bedroom, 2 bath - Raccoon Key, FL

Canal front, dockage, 2 bedroom, 2 bath

Cottage, Raccoon Key

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Raccoon Key, 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 Raccoon 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 $2,224.

From$318/night
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