Find 4 Star Hotels in Upper Matecumbe Key, FL from ￥24,188

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Check prices for these dates

Tonight
Nov 15 - Nov 16
Tomorrow
Nov 16 - Nov 17
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

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

Hawks Cay Resort
4.0 star property
Marathon
8.2 out of 10, Very good, (1,001 reviews)
"Lots of amenities and great staff will be coming back to this location"
United States
Holly
The price is ￥38,680
￥58,130 total
includes taxes & fees
Dec 9 - Dec 10
Hawks Cay Resort
A beach with lounge chairs and a pier extending into the water.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.8 out of 10, Excellent, (1,199 reviews)
"This was an amazing resort. Highly recommend!"
United States
Ryan
The price is ￥42,036
￥56,095 total
includes taxes & fees
Nov 29 - Nov 30
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,170 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is ￥37,053
￥53,363 total
includes taxes & fees
Nov 29 - Nov 30
Islander 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.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,332 reviews)
"Great location as well."
United States
Amir
The price is ￥25,769
￥40,671 total
includes taxes & fees
Nov 17 - Nov 18
Amara Cay Resort
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (314 reviews)
"Great stay!"
United States
Stephen
The price is ￥33,092
￥48,909 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
An aerial view of a resort with a large pool, palm trees, and a beach.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,004 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ￥42,004
￥56,059 total
includes taxes & fees
Nov 29 - Nov 30
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,003 reviews)
"Nice place, helpful staff, plenty of places to relax or just hang out."
United States
Mark
The price is ￥24,188
￥38,892 total
includes taxes & fees
Nov 17 - Nov 18
La Siesta Resort & Villas
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
4.0 star property
Marathon
8.0 out of 10, Very good, (234 reviews)
"Na"
United States
Kushla
The price is ￥73,307
￥92,354 total
includes taxes & fees
Nov 16 - Nov 17
Villas At Hawks Cay Resort
A beach with palm trees, lounge chairs, and a thatched-roof structure.

9. Condo in the Keys

Condo in the Keys
4.0 star property
Tavernier
8.2 out of 10, Very good, (17 reviews)
"Love the location "
United States
Angela
Condo in the Keys
A dining area with a glass table, chairs, and a vase with decorative flowers. There is a sofa and a television in the background.

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

Oceanfront Duck Key Villa: 2 Marinas Steps Away!
4.0 star property
Marathon
Oceanfront Duck Key Villa: 2 Marinas Steps Away!
Interior

11. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
4.0 star property
Long Key
Florida Keys Getaway w/ Stunning Ocean Views

Top Upper Matecumbe Key Hotel Reviews

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

Islander Resort

Islander Resort
Matecumbe

10/10 Excellent

Thoroughly enjoyed our stay! H-keeping was reliable in regards to linens/towels but a bit inconsistent when refreshing room amenities (coffee cups, etc).
United States
Patrick
Reviewed April 21, 2025
Islander Resort

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