A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

5 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $322

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Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Upper Matecumbe Key 5-star hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
John
CA $207
CA $335 total
includes taxes & fees
Sep 7 - Sep 8
Cheeca Lodge & Spa
A balcony with white furniture, a ceiling fan, and a view of a boat and water.
A bedroom with a wooden bed, white bedding, a woven hanging light, sheer curtains, a window with a view of palm trees, and a potted plant.
A two-story building with a balcony, surrounded by a white fence and palm trees.
A kitchen with wooden cabinets, a black countertop, and two bar stools.

2. Waterfront House with Boat Dock

Waterfront House with Boat Dock
Tavernier
United States
Philip J
Waterfront House with Boat Dock
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upper Matecumbe Key.
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
CA $258
CA $397 total
Sep 13 - Sep 14
includes taxes & fees
Hawks Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

97000 Overseas Hwy Key Largo FL
CA $330
CA $447 total
Sep 28 - Sep 29
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
CA $196
CA $322 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,298 reviews)
Amara Cay Resort
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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.

Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

See all hotels in Upper Matecumbe Key
A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
Photo by Cameron Abbott

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Everything was fabulous. We stayed in a newer building on the beach. The room, service, and staff were all 10/10. Shout out to Dee at the atlantics edge restaurant for her great dinner service. Our room was clean and replenished daily. The pool and poolside service also excellent. The only downside of our stay was the seaweed. The smell was bad at times. We would've liked to spend more time on the beach and look forward to coming back for that."
Bethanne 4-night trip
Posted 4 hours ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Luxury is the name of the game at the best 5 Stars hotels in Upper Matecumbe Key. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Upper Matecumbe Key 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Upper Matecumbe Key hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Upper Matecumbe Key without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Upper Matecumbe Key.

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