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

4 Star Hotels in Upper Matecumbe Key, Islamorada

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Upper Matecumbe Key 4-star hotels

A wooden deck with a view of the ocean and a palm tree.
A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.
A spacious interior with a high ceiling, large windows, and a central chandelier.
A spacious dining area with high ceilings, wicker furniture, and large windows.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Micheal
€324
includes taxes & fees
12 Oct - 13 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A pathway leading to a pool area with palm trees and a sunset view.
A modern living room with a balcony overlooking the sea, furnished with a sofa, chairs, and a dining table.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.

2. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Katherine
€251
includes taxes & fees
6 Oct - 7 Oct
Hawks Cay Resort
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.
A resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
MICHAEL
€217
includes taxes & fees
4 Oct - 5 Oct
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A beach with palm trees, a clear blue sky, and a calm sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
€277
includes taxes & fees
6 Oct - 7 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A wooden pier leading to a beach with palm trees and a row of beach huts.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

5. Islander Resort

Islander Resort
Matecumbe
United States
Steven
€348
includes taxes & fees
27 Oct - 28 Oct
Islander Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.
A beach with clear water, a wooden pier, and lounge chairs under a tree.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
€309
includes taxes & fees
13 Oct - 14 Oct
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A row of colorful beach huts with palm trees in the background.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A resort with a pool surrounded by palm trees and a view of the ocean.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
La Siesta Resort & Villas
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.
An aerial view of a resort island with a large building, a swimming pool, and a boat docked nearby.
A modern living room with a sofa, chairs, a dining table, a TV, and a view of the ocean.
A resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
United States
Gabriela
€429
includes taxes & fees
1 Oct - 2 Oct
Villas At Hawks Cay Resort
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.

9. Condo in the Keys

Condo in the Keys
Tavernier
United States
Angela
Condo in the Keys
A living room with a sofa, a glass coffee table, a television on a cabinet, and a sliding glass door leading to an outdoor area.
A kitchen with granite countertops, a stainless steel sink, a coffee maker, and a ceiling fan.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.
A sandy area with a water body, surrounded by greenery and a building with a flat roof.

10. Oceanfront Duck Key Villa: 2 Marinas Steps Away!

Oceanfront Duck Key Villa: 2 Marinas Steps Away!
Marathon
Oceanfront Duck Key Villa: 2 Marinas Steps Away!
Interior
A modern kitchen with a central island, bar stools, and a ceiling fan.
A beach with clear turquoise water, a wooden pier, and a rocky shoreline.
A modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.

11. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
Florida Keys Getaway w/ Stunning Ocean Views
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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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
€178
13 Oct - 14 Oct
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
€529
1 Oct - 2 Oct
includes taxes & fees
The Islands of Islamorada
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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

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

See all hotels in Upper Matecumbe Key
A sandy beach with palm trees and a clear blue sky.

Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Amazing place would definitely recommend"
Steven 2-night trip
Posted 1 day ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

8/10 Good
"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"
Melissa 1-night trip
Posted 1 day ago
Amara Cay Resort

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