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

Upper Matecumbe Key 4 Stars Hotels

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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 beach bar with a thatched roof, palm trees, and a view of the sea.
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
HK$1,859
HK$2,524 total
includes taxes & fees
1 Oct - 2 Oct
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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
MICHAEL
HK$1,213
HK$1,938 total
includes taxes & fees
29 Sept - 30 Sept
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A resort with a pool, beach, and ocean view.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
HK$1,563
HK$2,332 total
includes taxes & fees
29 Sept - 30 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.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.
A modern living room with a balcony overlooking the sea, furnished with a sofa, chairs, and a dining table.

4. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Katherine
HK$1,455
HK$2,240 total
includes taxes & fees
28 Sept - 29 Sept
Hawks Cay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A beach with clear water, a wooden pier, and lounge chairs under a tree.
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.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
HK$2,063
HK$2,754 total
includes taxes & fees
5 Oct - 6 Oct
Playa Largo Resort & Spa, Autograph Collection
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 bar area with a wooden counter, bar stools, and potted plants.
A paved pathway leading to a beach with palm trees and a view of the ocean.

6. Islander Resort

Islander Resort
Matecumbe
United States
John
HK$1,536
HK$2,257 total
includes taxes & fees
29 Sept - 30 Sept
Islander Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A beach with colorful buildings, kayaks, and lounge chairs.
A resort with a pool surrounded by palm trees and a view of the ocean.
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 resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.
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.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
United States
Gabriela
HK$2,973
HK$3,830 total
includes taxes & fees
1 Oct - 2 Oct
Villas At Hawks Cay Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A gated entrance to a resort with palm trees and a clear sky.

9. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
HK$3,248
HK$4,151 total
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.
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.

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 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.

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 a central island, bar stools, and a ceiling fan.
A modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.

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
HK$1,169
HK$1,889 total
8 Oct - 9 Oct
includes taxes & fees
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 Lorelei Restaurant & Cabana Bar 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

Amara Cay Resort

Amara Cay Resort

8/10 Good
"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"
Olga 2-night trip
Posted 2 hours ago
Amara Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

8/10 Good
"All was great, we just had an issue with a food item we ordered twice and was incorrectly doubled charged in both occasions. It looked liked a POS system issue, and the staff quickly resolved it. Other than that, everyone and everything was great. The resort is paradise by the beach ⛱️ 💯"
Luciana 1-night trip
Posted 9 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Islander Resort

Islander Resort

10/10 Excellent
"Nice pool"
Henry 1-night trip
Posted 1 day ago
Islander Resort
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel."
Miladis 2-night trip
Posted 1 day ago
Hawks Cay Resort

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