Vacation rentals in Boot Key Harbor, FL

Best Vacation rentals and Airbnb offers in Boot Key Harbor, FL

Waterfront Hideaway~ Canal Front Home, 24' Dock

Holiday Home, Boot Key Harbor

Waterfront Hideaway~ Canal Front Home, 24' Dock is a holiday home in Boot Key Harbor, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Waterfront Hideaway~ Canal Front Home, 24' Dock

Waterfront Hideaway~ Canal Front Home, 24' Dock is a holiday home in Boot Key Harbor, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,499.

From$114/night

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The Garden Villa Cozy 1BR Ground-Level Half Duplex with Private Pool

Holiday Home, Boot Key Harbor

The Garden Villa Cozy 1BR Ground-Level Half Duplex with Private Pool is a holiday home in Boot Key Harbor, with pool access and room for a group. This stay gives travelers a comfortable…

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About The Garden Villa Cozy 1BR Ground-Level Half Duplex with Private Pool

The Garden Villa Cozy 1BR Ground-Level Half Duplex with Private Pool is a holiday home in Boot Key Harbor, with 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,886.

From$131/night

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Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge.

Holiday Home, Boot Key Harbor

Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge. is a holiday home in Boot Key Harbor, with pet-friendly space, kitchen access,…

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About Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge.

Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge. is a holiday home in Boot Key Harbor, with pet-friendly space, 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: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,880.

From$136/night

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Marina View Escape with Pool, Tiki Bar & Marina

Condo, Boot Key Harbor

Marina View Escape with Pool, Tiki Bar & Marina is a condo in Boot Key Harbor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Marina View Escape with Pool, Tiki Bar & Marina

Marina View Escape with Pool, Tiki Bar & Marina is a condo in Boot Key Harbor, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,649.

From$140/night

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Browse Waterfront Vacation Rentals in Boot Key Harbor, FL

Discover vacation rentals close to the coast, water, and beach areas around Boot Key Harbor, FL.

Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores

Holiday Home, Boot Key Harbor

Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores is a holiday home in Boot Key Harbor, with pool access, easy beach access, and kitchen access. This stay…

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About Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores

Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores is a holiday home in Boot Key Harbor, 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 $2,208.

From$221/night

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UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH!

Holiday Home, Boot Key Harbor

UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH! is a holiday home in Boot Key Harbor, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH!

UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH! is a holiday home in Boot Key Harbor, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,322.

From$230/night

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Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic!

Holiday Home, Boot Key Harbor

Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic! is a holiday home in Boot Key Harbor, with pool access, easy beach access, and kitchen access. This stay gives…

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About Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic!

Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic! is a holiday home in Boot Key Harbor, 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 $3,354.

From$236/night

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Deep Water Canal, Swim Spa Pool, Kayaks, Walk to Ocean Front Bars & Restaurants!

Holiday Home, Boot Key Harbor

Deep Water Canal, Swim Spa Pool, Kayaks, Walk to Ocean Front Bars & Restaurants! is a holiday home in Boot Key Harbor, with pool access and easy beach access. This stay gives travelers a…

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About Deep Water Canal, Swim Spa Pool, Kayaks, Walk to Ocean Front Bars & Restaurants!

Deep Water Canal, Swim Spa Pool, Kayaks, Walk to Ocean Front Bars & Restaurants! is a holiday home in Boot Key Harbor, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,397.

From$239/night

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Browse Vacation Rentals with a Pool in Boot Key Harbor, FL

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

Waterfront Luxury Condo with Pool + Tiki Bar

Condo, Boot Key Harbor

Waterfront Luxury Condo with Pool + Tiki Bar is a condo in Boot Key Harbor, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront Luxury Condo with Pool + Tiki Bar

Waterfront Luxury Condo with Pool + Tiki Bar is a condo in Boot Key Harbor, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,922.

From$164/night

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Brand New Marina Suite with Pool + Free Breakfast

Condo, Boot Key Harbor

Brand New Marina Suite with Pool + Free Breakfast is a condo in Boot Key Harbor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Brand New Marina Suite with Pool + Free Breakfast

Brand New Marina Suite with Pool + Free Breakfast is a condo in Boot Key Harbor, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,874.

From$165/night

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New Waterfront Suite with Pool + Free Breakfast

Condo, Boot Key Harbor

New Waterfront Suite with Pool + Free Breakfast is a condo in Boot Key Harbor, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About New Waterfront Suite with Pool + Free Breakfast

New Waterfront Suite with Pool + Free Breakfast is a condo in Boot Key Harbor, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,887.

From$167/night

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Marina View Villa with Pool & Tiki Bar

Condo, Boot Key Harbor

Marina View Villa with Pool & Tiki Bar is a condo in Boot Key Harbor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Marina View Villa with Pool & Tiki Bar

Marina View Villa with Pool & Tiki Bar is a condo in Boot Key Harbor, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,910.

From$169/night

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Best Boot Key Harbor, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cozy apartment in Marathon key

Condo, Boot Key Harbor

Cozy apartment in Marathon key is a condo in Boot Key Harbor, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy apartment in Marathon key

Cozy apartment in Marathon key is a condo in Boot Key Harbor, 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: free cancellation, pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,674.

From$171/night

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Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴

Holiday Home, Boot Key Harbor

Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴 is a holiday home in Boot Key Harbor, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴

Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴 is a holiday home in Boot Key Harbor, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,026.

From$173/night

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Chill Island Vibes & Sunrises: Your Private Paradise in the Florida Keys!

Holiday Home, Boot Key Harbor

Chill Island Vibes & Sunrises: Your Private Paradise in the Florida Keys! is a holiday home in Boot Key Harbor, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Chill Island Vibes & Sunrises: Your Private Paradise in the Florida Keys!

Chill Island Vibes & Sunrises: Your Private Paradise in the Florida Keys! is a holiday home in Boot Key Harbor, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,691.

From$180/night

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Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC

Condo, Boot Key Harbor

Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC is a condo in Boot Key Harbor, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC

Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC is a condo in Boot Key Harbor, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,696.

From$195/night

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Best Pet-Friendly Vacation Rentals in Boot Key Harbor, FL

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

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island.

Holiday Home, Boot Key Harbor

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island. is a holiday home in Boot Key Harbor, with pet-friendly space, kitchen access, and room for a…

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About Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island.

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island. is a holiday home in Boot Key Harbor, with pet-friendly space, 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: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,410.

From$184/night

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Boater’s Seaside Dream 45 ft dock M#13

Holiday Home, Boot Key Harbor

Boater’s Seaside Dream 45 ft dock M#13 is a holiday home in Boot Key Harbor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Boater’s Seaside Dream 45 ft dock M#13

Boater’s Seaside Dream 45 ft dock M#13 is a holiday home in Boot Key Harbor, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,408.

From$196/night

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Boot Key Harbor Oasis a 2-bedroom, 2-bath half duplex on Boot Key Harbor

Holiday Home, Boot Key Harbor

Boot Key Harbor Oasis a 2-bedroom, 2-bath half duplex on Boot Key Harbor is a holiday home in Boot Key Harbor, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Boot Key Harbor Oasis a 2-bedroom, 2-bath half duplex on Boot Key Harbor

Boot Key Harbor Oasis a 2-bedroom, 2-bath half duplex on Boot Key Harbor is a holiday home in Boot Key Harbor, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,506.

From$205/night

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Waterfront Luxury Living Inside & Out, Gulf View, On the Water!!

Condo, Boot Key Harbor

Waterfront Luxury Living Inside & Out, Gulf View, On the Water!! is a condo in Boot Key Harbor, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Waterfront Luxury Living Inside & Out, Gulf View, On the Water!!

Waterfront Luxury Living Inside & Out, Gulf View, On the Water!! is a condo in Boot Key Harbor, 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 $1,970.

From$208/night

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Best Boot Key Harbor, FL vacation rentals with a kitchen

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

M18 - Spacious 3 bedroom, 2 bath Gulf side condo!

Condo, Boot Key Harbor

M18 - Spacious 3 bedroom, 2 bath Gulf side condo! is a condo in Boot Key Harbor, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About M18 - Spacious 3 bedroom, 2 bath Gulf side condo!

M18 - Spacious 3 bedroom, 2 bath Gulf side condo! is a condo in Boot Key Harbor, 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 $2,081.

From$179/night

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Island Time Escape – Resort Stay #405, Island Time Resort

Apartment, Boot Key Harbor

Island Time Escape – Resort Stay #405, Island Time Resort is a apartment in Boot Key Harbor, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Island Time Escape – Resort Stay #405, Island Time Resort

Island Time Escape – Resort Stay #405, Island Time Resort is a apartment in Boot Key Harbor, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,586.

From$219/night

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Keyz Style 3BR/3B Heated Pool, 50' ft dock w/ deep access to Atlantic and Gulf

Holiday Home, Boot Key Harbor

Keyz Style 3BR/3B Heated Pool, 50' ft dock w/ deep access to Atlantic and Gulf is a holiday home in Boot Key Harbor, with pet-friendly space, pool access, and easy beach access. This stay…

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About Keyz Style 3BR/3B Heated Pool, 50' ft dock w/ deep access to Atlantic and Gulf

Keyz Style 3BR/3B Heated Pool, 50' ft dock w/ deep access to Atlantic and Gulf is a holiday home in Boot Key Harbor, 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 $2,247.

From$225/night

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W16 - 3 bed, 2 bath Tropical Bungalow with Dockage

Holiday Home, Boot Key Harbor

W16 - 3 bed, 2 bath Tropical Bungalow with Dockage is a holiday home in Boot Key Harbor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About W16 - 3 bed, 2 bath Tropical Bungalow with Dockage

W16 - 3 bed, 2 bath Tropical Bungalow with Dockage is a holiday home in Boot Key Harbor, with 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 $2,755.

From$250/night

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