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25 Jul - 27 Jul
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1 Aug - 3 Aug
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15 Aug - 17 Aug
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Browse Select Upper Matecumbe Key Holiday Homes

Angler's Reef Resort by KeysCaribbean
Stroll along the natural coastal path, surrounded by lush greenery and serene atmosphere.

Angler's Reef Resort by KeysCaribbean

3.5 star property
9.0 out of 10, Wonderful, (14)
"House is situated right off the main road and very noisy at all times day and night. Also no blinds in the Master room which is located at back of home off the road. Had to buy a set of frying pans because the pans there were in terrible condition for Teflon coated."
Angler's Reef Resort by KeysCaribbean
Mariner's Club Key Largo by KeysCaribbean
Relax by the pool surrounded by lush greenery and palm trees, with sun loungers and a poolside bar at your fingertips.

Mariner's Club Key Largo by KeysCaribbean

3.5 star property
7.4 out of 10, Good, (263)
"Great property "
Mariner's Club Key Largo by KeysCaribbean
Holly s Hideout in Islamorada
Relax by the pool surrounded by lush greenery and a marina view.

Holly s Hideout in Islamorada

2.0 star property
Holly s Hideout in Islamorada
Lime Key in Key Largo
Enjoy the ocean view from the balcony, where you can relax with a glass table and wicker furniture.

Lime Key in Key Largo

2.0 star property
Lime Key in Key Largo
The Caribbean Resort Malayan Palm East
Relax on a well-maintained beach with a wooden deck and thatched-roof pavilion.

The Caribbean Resort Malayan Palm East

3.5 star property
The Caribbean Resort Malayan Palm East
The Caribbean Resort Canary Island Palm South
Relax on a well-maintained beach with a wooden deck, pool, and pier.

The Caribbean Resort Canary Island Palm South

3.5 star property
The Caribbean Resort Canary Island Palm South
Sunset Beach in Key Largo
Enjoy a tranquil retreat on your balcony with a hot tub, wooden bench, and stunning beach views.

Sunset Beach in Key Largo

2.0 star property
Sunset Beach in Key Largo
The Caribbean Resort Royal Palm North
Relax by the tranquil pool or on the sandy beach with a clear ocean view.

The Caribbean Resort Royal Palm North

3.5 star property
The Caribbean Resort Royal Palm North
The Caribbean Resort Jamaican Palm House
Relax by the tranquil pool or under the shade of a thatched-roof pavilion overlooking the ocean.

The Caribbean Resort Jamaican Palm House

3.5 star property
The Caribbean Resort Jamaican Palm House
The Caribbean Resort Princess Palm South
Enjoy a serene beachfront setting with a clear ocean view from the deck, surrounded by lush greenery and palm trees.

The Caribbean Resort Princess Palm South

3.5 star property
The Caribbean Resort Princess Palm South
The Caribbean Resort Fish Tail Palm
Relax by the ocean with a serene beachfront setting, featuring a dock and lounge area.

The Caribbean Resort Fish Tail Palm

3.5 star property
The Caribbean Resort Fish Tail Palm
The Caribbean Resort Canary Island Palm North
Enjoy a serene beachfront setting with ocean views, a wooden deck, and a small pool with a dock.

The Caribbean Resort Canary Island Palm North

3.5 star property
The Caribbean Resort Canary Island Palm North
Oleander Hideaway
Enjoy meals in this dining area with a wooden table and six chairs, surrounded by a ceiling fan and natural light.

Oleander Hideaway

3.5 star property
Oleander Hideaway
Brand New Key Largo Home
Enjoy cooking in this well-equipped kitchen with a granite countertop, stainless steel appliances, and large window offering views of the surrounding area.

Brand New Key Largo Home

3.5 star property
Brand New Key Largo Home
The Caribbean Resort Bird of Paradise - One Bedroom One Bath
Relax by the tranquil pool or on the sandy beach with a clear ocean view.

The Caribbean Resort Bird of Paradise - One Bedroom One Bath

3.5 star property
The Caribbean Resort Bird of Paradise - One Bedroom One Bath
The Caribbean Resort Coconut Palm North
Relax on a well-maintained beach with a tranquil pool and shaded pavilion.

The Caribbean Resort Coconut Palm North

4.0 star property
The Caribbean Resort Coconut Palm North
Serenity by Florida Keys Luxury Rentals
House, 3 Bedrooms | Pool

Serenity by Florida Keys Luxury Rentals

4.0 star property
Serenity by Florida Keys Luxury Rentals
Pineapple Beach by Florida Keys Luxury Rentals
House, 5 Bedrooms | Beach/ocean view

Pineapple Beach by Florida Keys Luxury Rentals

4.0 star property
Pineapple Beach by Florida Keys Luxury Rentals
Lime Key by Florida Keys Luxury Rentals
House, 3 Bedrooms | Balcony

Lime Key by Florida Keys Luxury Rentals

4.0 star property
Lime Key by Florida Keys Luxury Rentals
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"The resort was beautiful and although it was sold out it never seemed med to crowded. "
Yoiss 2-night trip
Posted 11 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton