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

Compare and book 4 Star hotels in Upper Matecumbe Key, Islamorada

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
14 Sept - 15 Sept
Tomorrow
15 Sept - 16 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

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 modern hotel lobby with large windows, geometric light fixtures, and indoor plants.
A modern hotel room with a large bed, a desk with a lamp, a chair, and a view of the ocean.

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
Milagros
£238
includes taxes & fees
28 Sept - 29 Sept
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 beach with palm trees, a dock, and lounge chairs.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Amy
£166
includes taxes & fees
27 Sept - 28 Sept
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.
A resort with a pool, beach, and ocean view.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
£206
includes taxes & fees
27 Sept - 28 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A spacious lobby with high ceilings, large windows, and a central coffee table surrounded by sofas and chairs.
A pathway leading to a pool area with palm trees and a sunset view.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.

4. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Clara
£211
includes taxes & fees
21 Sept - 22 Sept
Hawks Cay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
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.
A beachside patio with lounge chairs, a table, and a view of the ocean.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Danilo
£253
includes taxes & fees
28 Sept - 29 Sept
Playa Largo Resort & Spa, Autograph Collection
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
A paved pathway leading to a beach with palm trees and a view of the ocean.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.
A bar area with a wooden counter, bar stools, and potted plants.

6. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
£213
includes taxes & fees
27 Sept - 28 Sept
Islander Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach resort with palm trees, a thatched hut, and a purple building with a window.
A beach with colorful buildings, kayaks, and lounge chairs.
A row of colorful beach huts with palm trees in the background.

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.
A modern living room with a sofa, chairs, a dining table, a TV, and a view of the ocean.
A modern kitchen with white cabinetry, a stainless steel oven, and a large island with a bowl of fruit.
An aerial view of a resort island with a large building, a swimming pool, and a boat docked nearby.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
United States
Gabriela
£361
includes taxes & fees
15 Sept - 16 Sept
Villas At Hawks Cay Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A pool area with clear blue water, white lounge chairs, and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

9. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
£384
includes taxes & fees
15 Sept - 16 Sept
The Islands of Islamorada
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.
A spacious living room with a dining area, a sofa, and a coffee table.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.

10. 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 living room with a sofa, armchair, and coffee table, a dining area with a table and chairs, and a kitchen in the background.
A sandy area with a water body, surrounded by greenery and a building with a flat roof.
A kitchen with granite countertops, a stainless steel sink, a coffee maker, and a ceiling fan.

11. 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!
A modern kitchen with white cabinetry, a built-in oven, and a large island with stools.
A modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.
A beach with clear turquoise water, a wooden pier, and a rocky shoreline.

12. 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
£153
15 Sept - 16 Sept
includes taxes & fees
9.2/10 Wonderful! (1,440 reviews)
Cheeca Lodge & Spa
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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 beachside café with colorful chairs and tables, palm trees, and a view of the ocean.

Top Upper Matecumbe Key Hotel Reviews

Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"Just returned from Hawks Cay, we loved the property in general. The big pool, the lagoon, the outdoor spaces all well maintained. It was our first time here and we appreciated the modern decoration of the lobby and all the areas around it, the breakfast cafe and the restaurant . We stayed at the Pool Cabana room, perfect location in front of the main pool. The room was spacious , with a mini fridge and a coffee maker. Good lighting and space to store your things. My only suggestion would be to improve the beddings and mattresses. Overall I got the feeling of a good old time American resort. Perfect for families since the kids can be at the pool, or kayaking at the lagoon or even fishing. We recommend it 👍"
Rosanna 3-night trip
Posted 8 hours ago
Hawks Cay Resort
Islander Resort

Islander Resort

10/10 Excellent
"Great location. Very good CLEANING staff and FRONT DESK staff are excellent"
Thomas 4-night trip
Posted 9 hours ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Beautiful lobby, nice outdoor area, room is clean, the elevator is a bit old though. Pool is very big, kids love it."
Yimin 1-night trip
Posted 1 day ago
Amara Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"The hotel is very lovely and cozy, the entire staff is very friendly, and the areas and rooms are very clean; I recommend it."
juan 2-night trip
Posted 1 day ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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