Vacation rentals in Upper Matecumbe Key, FL

Best Vacation rentals and Airbnb offers in Upper Matecumbe Key, FL

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

Apartment, Upper Matecumbe Key

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

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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 Upper Matecumbe 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 $1,611.

From$185/night

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Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Apartment, Upper Matecumbe Key

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! is a apartment in Upper Matecumbe Key, with pet-friendly space, pool access, and parking. This stay gives…

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About Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! is a apartment in Upper Matecumbe 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 $1,611.

From$185/night

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

Villa, Upper Matecumbe Key

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only! is a villa in Upper Matecumbe 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 Upper Matecumbe 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 $2,748.

From$225/night

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Oceanfront Private Cottage!

Cottage, Upper Matecumbe Key

Oceanfront Private Cottage! is a cottage in Upper Matecumbe Key, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Oceanfront Private Cottage!

Oceanfront Private Cottage! is a cottage in Upper Matecumbe Key, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,188.

From$225/night

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Browse Vacation Rentals with a Pool in Upper Matecumbe Key, FL

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

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Apartment, Upper Matecumbe Key

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast is a apartment in Upper Matecumbe Key, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast is a apartment in Upper Matecumbe 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 $1,918.

From$219/night

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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Apartment, Upper Matecumbe Key

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast is a apartment in Upper Matecumbe Key, with pet-friendly space, pool access, and parking. This stay gives…

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About Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast is a apartment in Upper Matecumbe 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 $2,850.

From$295/night

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

Apartment, Upper Matecumbe Key

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Upper Matecumbe 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 Upper Matecumbe 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 $2,816.

From$295/night

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New Caribbean home. Resort access to pool

Holiday Home, Upper Matecumbe Key

New Caribbean home. Resort access to pool is a holiday home in Upper Matecumbe Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About New Caribbean home. Resort access to pool

New Caribbean home. Resort access to pool is a holiday home in Upper Matecumbe 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, beachfront, beach front, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,881.

From$325/night

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Best Upper Matecumbe Key, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

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

Apartment, Upper Matecumbe Key

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Upper Matecumbe 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 Upper Matecumbe 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 $1,918.

From$219/night

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

Apartment, Upper Matecumbe Key

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

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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 Upper Matecumbe 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 $2,209.

From$252/night

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

Apartment, Upper Matecumbe Key

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

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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 Upper Matecumbe 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 $2,209.

From$252/night

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

Apartment, Upper Matecumbe Key

Steps to Windley Key! Pet-friendly Villa! Marina, FREE Parking, Pool! is a apartment in Upper Matecumbe 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 Upper Matecumbe 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 $2,231.

From$252/night

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Best Pet-Friendly Vacation Rentals in Upper Matecumbe Key, FL

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

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

Apartment, Upper Matecumbe Key

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

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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 Upper Matecumbe 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 $1,656.

From$190/night

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

Apartment, Upper Matecumbe Key

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

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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 Upper Matecumbe 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 $1,656.

From$190/night

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Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!

Apartment, Upper Matecumbe Key

Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental! is a apartment in Upper Matecumbe Key, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!

Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental! is a apartment in Upper Matecumbe 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 $1,718.

From$197/night

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

Apartment, Upper Matecumbe Key

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking is a apartment in Upper Matecumbe 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 Upper Matecumbe 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 $1,812.

From$207/night

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Best Upper Matecumbe Key, FL vacation rentals with a kitchen

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

Spring & summer dates available licensed rental vr #25-0235 NO BOATS

Condo, Upper Matecumbe Key

Spring & summer dates available licensed rental vr #25-0235 NO BOATS is a condo in Upper Matecumbe Key, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Spring & summer dates available licensed rental vr #25-0235 NO BOATS

Spring & summer dates available licensed rental vr #25-0235 NO BOATS is a condo in Upper Matecumbe 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: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,764.

From$157/night

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Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Apartment, Upper Matecumbe Key

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Upper Matecumbe Key, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Upper Matecumbe 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 $2,081.

From$238/night

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

Holiday Home, Upper Matecumbe Key

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families. is a holiday home in Upper Matecumbe 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 Upper Matecumbe 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 $3,082.

From$295/night

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Experience the beauty of Islamorada in this 2BR upper-level with stunning water views.

Holiday Home, Upper Matecumbe Key

Experience the beauty of Islamorada in this 2BR upper-level with stunning water views. is a holiday home in Upper Matecumbe Key, with pet-friendly space, kitchen access, and room for a…

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About Experience the beauty of Islamorada in this 2BR upper-level with stunning water views.

Experience the beauty of Islamorada in this 2BR upper-level with stunning water views. is a holiday home in Upper Matecumbe Key, 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 $4,241.

From$442/night

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Our Favorite Family-Friendly Vacation Rentals in Upper Matecumbe Key, FL

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

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

Cottage, Upper Matecumbe Key

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool is a cottage in Upper Matecumbe Key, 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 Upper Matecumbe 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: 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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Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment

Apartment, Upper Matecumbe Key

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment is a apartment in Upper Matecumbe 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 Upper Matecumbe 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 $2,209.

From$252/night

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

Cottage, Upper Matecumbe Key

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More is a cottage in Upper Matecumbe 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 Upper Matecumbe 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 $4,223.

From$399/night

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New Ground Level Caribbean Cottage

Holiday Home, Upper Matecumbe Key

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

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About New Ground Level Caribbean Cottage

New Ground Level Caribbean Cottage is a holiday home in Upper Matecumbe 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 $3,764.

From$425/night

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