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

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Check availability on Upper Matecumbe Key 4 Star Hotels

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Our top choices for Upper Matecumbe Key 4-star hotels

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

1. Hawks Cay Resort

Marathon

Holly

includes taxes & fees

15 Nov - 16 Nov

A beach with lounge chairs and a pier extending into the water.

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

Key Largo

Damion

includes taxes & fees

10 Nov - 11 Nov

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Matecumbe

DEBORAH

includes taxes & fees

1 Nov - 2 Nov

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

4. Amara Cay Resort

Matecumbe

Amir

includes taxes & fees

15 Nov - 16 Nov

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

5. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

Liosbel

includes taxes & fees

29 Nov - 30 Nov

An aerial view of a resort with a large pool, palm trees, and a beach.

6. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Jorge

includes taxes & fees

29 Nov - 30 Nov

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

Matecumbe

Brianne

includes taxes & fees

15 Nov - 16 Nov

A resort pool with palm trees and lounge chairs, surrounded by a beachfront.

8. Villas At Hawks Cay Resort

Marathon

Gabriela

includes taxes & fees

16 Nov - 17 Nov

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Explore similar 5-star hotels

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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

£189

1 Nov - 2 Nov

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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

Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key.

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A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top Upper Matecumbe Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent

"This was by far the best hotel I have ever stayed in. It caters for all of your needs and you don’t have to leave the hotel at all if you don’t want to. They have thought about every little detail. I hope to come back one day"

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