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

Find 4 Star Hotels in Upper Matecumbe Key, FL from ￥34,202

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Upper Matecumbe Key 4-star hotels

A wooden deck with a view of the ocean and a palm tree.
A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious dining area with high ceilings, wicker furniture, and large windows.
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.

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
￥43,746
￥57,890 total
includes taxes & fees
Oct 18 - Oct 19
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.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.
A spacious lobby with high ceilings, large windows, and a central coffee table surrounded by sofas and chairs.

2. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Katherine
￥29,191
￥44,939 total
includes taxes & fees
Oct 7 - Oct 8
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.
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.
A beach with palm trees, a dock, and lounge chairs.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
MICHAEL
￥22,384
￥36,693 total
includes taxes & fees
Oct 19 - Oct 20
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.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A coastal resort with a beach, a swimming pool, and multiple buildings.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
Canada
Eslita
￥33,866
￥49,607 total
includes taxes & fees
Oct 18 - Oct 19
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 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.
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

5. Islander Resort

Islander Resort
Matecumbe
United States
Steven
￥38,293
￥54,590 total
includes taxes & fees
Oct 27 - Oct 28
Islander 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.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
￥41,388
￥55,237 total
includes taxes & fees
Oct 15 - Oct 16
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 resort with a pool surrounded by palm trees and a view of the ocean.
A beach with colorful buildings, kayaks, and lounge chairs.

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
￥59,658
￥76,856 total
includes taxes & fees
Oct 1 - Oct 2
Villas At Hawks Cay Resort
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 restaurant with a bar area, wooden ceiling, large windows, and potted plants.
A spacious living room with a dining area, a sofa, and a coffee table.

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 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.
A living room with a sofa, armchair, and coffee table, a dining area with a table and chairs, and a kitchen in the background.

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 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.
A modern kitchen with white cabinetry, a built-in oven, and a large island with stools.

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
￥20,170
￥34,202 total
Oct 1 - Oct 2
includes taxes & fees
9.2/10 Wonderful! (1,470 reviews)
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
￥74,298
￥93,749 total
Oct 28 - Oct 29
includes taxes & fees
The Islands of Islamorada
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Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

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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