Vacation rentals in Anne's Beach, FL

Best Vacation rentals and Airbnb offers in Anne's Beach, FL

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool

Cottage, Anne's Beach

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool is a cottage in Anne's Beach, with pool access, parking, and kitchen access. This stay gives travelers a…

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About 2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool is a cottage in Anne's Beach, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,098.

From$208/night

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Gulf View Retreat @ Bay Harbor

Condo, Anne's Beach

Gulf View Retreat @ Bay Harbor is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Gulf View Retreat @ Bay Harbor

Gulf View Retreat @ Bay Harbor is a condo in Anne's Beach, 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 $2,490.

From$235/night

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AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

Condo, Anne's Beach

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!! is a condo in Anne's Beach, with pool access and easy beach access. This stay gives travelers a comfortable…

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About AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!! is a condo in Anne's Beach, 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 $2,707.

From$259/night

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Coastal Studio Getaway – Second Floor with Partial Water Views

Apartment, Anne's Beach

Coastal Studio Getaway – Second Floor with Partial Water Views is a apartment in Anne's Beach, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views is a apartment in Anne's Beach, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,713.

From$282/night

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Browse Waterfront Vacation Rentals in Anne's Beach, FL

Discover vacation rentals close to the coast, water, and beach areas around Anne's Beach, FL.

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Condo, Anne's Beach

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis, is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis, is a condo in Anne's Beach, 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 $3,516.

From$365/night

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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Condo, Anne's Beach

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities is a condo in Anne's Beach, with pool access, easy beach access, and room for a group. This stay gives…

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About Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities is a condo in Anne's Beach, 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 $3,840.

From$398/night

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Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada

Condo, Anne's Beach

Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada

Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada is a condo in Anne's Beach, 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 $4,382.

From$411/night

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Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada.

Condo, Anne's Beach

Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada. is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives…

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About Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada.

Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada. is a condo in Anne's Beach, 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 $4,575.

From$442/night

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Browse Vacation Rentals with a Pool in Anne's Beach, FL

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

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!

Condo, Anne's Beach

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS! is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS! is a condo in Anne's Beach, 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 $2,998.

From$314/night

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Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Condo, Anne's Beach

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access is a condo in Anne's Beach, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access is a condo in Anne's Beach, with pool access, kitchen 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,300.

From$346/night

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Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Apartment, Anne's Beach

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 is a apartment in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives…

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About Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 is a apartment in Anne's Beach, 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 $3,253.

From$346/night

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3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!

Condo, Anne's Beach

3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views! is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About 3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!

3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views! is a condo in Anne's Beach, 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 $4,014.

From$364/night

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Best Anne's Beach, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Waterfront & snowbird-friendly studio with dock & quick open water access

Apartment, Anne's Beach

Waterfront & snowbird-friendly studio with dock & quick open water access is a apartment in Anne's Beach, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Waterfront & snowbird-friendly studio with dock & quick open water access

Waterfront & snowbird-friendly studio with dock & quick open water access is a apartment in Anne's Beach, with easy beach 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,321.

From$150/night

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Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Holiday Home, Anne's Beach

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,813.

From$303/night

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Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Holiday Home, Anne's Beach

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, with pool access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, with 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: pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,813.

From$303/night

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Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.

Condo, Anne's Beach

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key. is a condo in Anne's Beach, with easy beach access, parking, and kitchen access. This stay gives…

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About Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key. is a condo in Anne's Beach, with easy beach 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: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,745.

From$361/night

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Best Pet-Friendly Vacation Rentals in Anne's Beach, FL

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

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Villa, Anne's Beach

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only! is a villa in Anne's Beach, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only! is a villa in Anne's Beach, 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 $2,748.

From$225/night

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Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

Villa, Anne's Beach

Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly is a villa in Anne's Beach, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable…

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About Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly is a villa in Anne's Beach, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,335.

From$268/night

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Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!

Apartment, Anne's Beach

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly! is a apartment in Anne's Beach, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly! is a apartment in Anne's Beach, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,538.

From$271/night

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*Charming Beach House directly ON the beach

Holiday Home, Anne's Beach

*Charming Beach House directly ON the beach is a holiday home in Anne's Beach, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About *Charming Beach House directly ON the beach

*Charming Beach House directly ON the beach is a holiday home in Anne's Beach, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,123.

From$525/night

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Best Anne's Beach, FL vacation rentals with a kitchen

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

A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included

Holiday Home, Anne's Beach

A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included is a holiday home in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included

A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included is a holiday home in Anne's Beach, 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 $3,366.

From$286/night

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Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Holiday Home, Anne's Beach

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada is a holiday home in Anne's Beach, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,813.

From$303/night

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Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views

Condo, Anne's Beach

Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views

Islamorada Waterfront Penthouse with 50' Private Boat Slip & Ocean Views is a condo in Anne's Beach, 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 $4,605.

From$442/night

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Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK

Condo, Anne's Beach

Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK is a condo in Anne's Beach, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK

Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK is a condo in Anne's Beach, 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 $4,742.

From$516/night

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