Vacation rentals in Panhandle Key, FL

Best vacation rentals and Airbnb offers in Panhandle Key, FL

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Apartment, Panhandle Key

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast is a apartment in Panhandle Key, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast is a apartment in Panhandle Key, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,677.

From$240/night

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Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental

Apartment, Panhandle Key

Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental

Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental is a apartment in Panhandle 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 $1,718.

From$245/night

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Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool

Apartment, Panhandle Key

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool is a apartment in Panhandle 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 $1,718.

From$245/night

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Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking

Apartment, Panhandle Key

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking is a apartment in Panhandle Key, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking is a apartment in Panhandle Key, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,859.

From$266/night

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Vacation rentals with a pool in Panhandle Key, FL

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

Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool!

Apartment, Panhandle Key

Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool! is a apartment in Panhandle Key, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool!

Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool! is a apartment in Panhandle 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,239.

From$320/night

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Spacious Villa! Private Beach Access, Pets Allowed, Free Breakfast!

Apartment, Panhandle Key

Spacious Villa! Private Beach Access, Pets Allowed, Free Breakfast! is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Spacious Villa! Private Beach Access, Pets Allowed, Free Breakfast!

Spacious Villa! Private Beach Access, Pets Allowed, Free Breakfast! is a apartment in Panhandle 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 $2,364.

From$338/night

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Island Escape in Islamorada | Breakfast, Pool & Pet-Friendly Stay!

Apartment, Panhandle Key

Island Escape in Islamorada · Breakfast, Pool & Pet-Friendly Stay! is a apartment in Panhandle Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Island Escape in Islamorada | Breakfast, Pool & Pet-Friendly Stay!

Island Escape in Islamorada · Breakfast, Pool & Pet-Friendly Stay! is a apartment in Panhandle 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 $2,480.

From$354/night

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

Villa, Panhandle Key

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

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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 Panhandle 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 $2,502.

From$357/night

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Vacation rentals with parking in Panhandle Key, FL

Find vacation rentals that make arriving by car easier.

Caloosa Cove Resort by CoolVacay

Condo, Panhandle Key

Caloosa Cove Resort by CoolVacay is a condo in Panhandle Key, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay is a condo in Panhandle Key, 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 $2,753.

From$320/night

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Villa located on the water Free marina, and trailer parking.

Holiday Home, Panhandle Key

Villa located on the water Free marina, and trailer parking. is a holiday home in Panhandle Key, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Villa located on the water Free marina, and trailer parking.

Villa located on the water Free marina, and trailer parking. is a holiday home in Panhandle 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 cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,505.

From$358/night

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

Villa, Panhandle Key

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,535.

From$362/night

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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Apartment, Panhandle Key

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Panhandle Key, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Panhandle 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,557.

From$365/night

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Pet-friendly vacation rentals in Panhandle Key, FL

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

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Apartment, Panhandle Key

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast is a apartment in Panhandle 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 $2,217.

From$317/night

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Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Apartment, Panhandle Key

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast

Classic Villa w/ Ocean View & Balcony! Beach Access, FREE Parking & Breakfast is a apartment in Panhandle 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 $2,217.

From$317/night

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Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!

Apartment, Panhandle Key

Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool! is a apartment in Panhandle Key, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!

Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool! is a apartment in Panhandle 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,217.

From$317/night

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Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast

Apartment, Panhandle Key

Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast is a apartment in Panhandle Key, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast

Sportfishing in Florida Keys! Elegant Villa w/ Beach Access and Pool! Breakfast is a apartment in Panhandle 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 $2,217.

From$317/night

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Vacation rentals with a kitchen in Panhandle Key, FL

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

Gulf View Retreat @ Bay Harbor

Condo, Panhandle Key

Gulf View Retreat @ Bay Harbor is a condo in Panhandle Key, 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 Panhandle 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,268.

From$324/night

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Flip-Flops & Sunshine: Islamorada Studio Escape

Condo, Panhandle Key

Flip-Flops & Sunshine: Islamorada Studio Escape is a condo in Panhandle Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape is a condo in Panhandle Key, 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 $2,440.

From$349/night

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

Condo, Panhandle Key

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS! is a condo in Panhandle Key, 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 Panhandle 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 $2,695.

From$385/night

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Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock

Villa, Panhandle Key

Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock is a villa in Panhandle Key, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock

Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock is a villa in Panhandle Key, 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,858.

From$408/night

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Family-friendly vacation rentals in Panhandle Key, FL

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

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment

Apartment, Panhandle Key

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment is a apartment in Panhandle Key, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment is a apartment in Panhandle Key, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,217.

From$317/night

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Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Holiday Home, Panhandle Key

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families. is a holiday home in Panhandle Key, with pet-friendly space and kitchen access. This stay gives…

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About Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families. is a holiday home in Panhandle Key, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,781.

From$397/night

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New Ground Level Caribbean Cottage

Holiday Home, Panhandle Key

New Ground Level Caribbean Cottage is a holiday home in Panhandle Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About New Ground Level Caribbean Cottage

New Ground Level Caribbean Cottage is a holiday home in Panhandle Key, with 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, beachfront, beach front, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,392.

From$485/night

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Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More

Cottage, Panhandle Key

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More is a cottage in Panhandle Key, with pool access and easy beach access. This stay gives travelers a…

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About Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More is a cottage in Panhandle Key, 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 $3,811.

From$544/night

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