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
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Upper Matecumbe Key 4-star hotels

A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A cozy living room with a pool table, a large bookshelf, and comfortable seating.
A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.
A child sitting on a beach with sand toys and a green bucket nearby.

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
Alan
P18,512
P24,293 total
includes taxes & fees
Oct 28 - Oct 29
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
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.
A pathway leading to a pool area with palm trees and a sunset view.

2. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Antonio
P12,683
P19,103 total
includes taxes & fees
Oct 22 - Oct 23
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 beach with palm trees, a dock, and lounge chairs.
A resort pool with palm trees, beach chairs, and umbrellas.
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
Danielle
P9,720
P15,534 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.
An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.
A resort with a pool, beach, and ocean view.
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
United States
Liosbel
P15,082
P21,579 total
includes taxes & fees
Nov 2 - Nov 3
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
P13,115
P19,365 total
includes taxes & fees
Oct 18 - Oct 19
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 beachside patio with lounge chairs, a table, and a view of the ocean.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
P17,545
P23,205 total
includes taxes & fees
Oct 29 - Oct 30
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
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.
A beach with colorful buildings, kayaks, and lounge chairs.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
P9,746
P15,576 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A resort pool with palm trees and lounge chairs, surrounded by a beachfront.
A modern kitchen with white cabinetry, a stainless steel oven, and a large island with a bowl of fruit.
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.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
United States
Gabriela
P28,941
P36,461 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.
A spacious living room with a dining area, a sofa, and a coffee table.
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.

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 a central island, bar stools, and a ceiling fan.
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
P35,688
P66,181 total
includes taxes & fees
Oct 28 - Oct 29
Florida Keys Getaway w/ Stunning Ocean Views
Property grounds
Exterior
Private kitchen
Pool

12. Pineapple Beach by Florida Keys Luxury Rentals

Pineapple Beach by Florida Keys Luxury Rentals
Islamorada
Pineapple Beach by Florida Keys Luxury Rentals
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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
P12,514
P18,677 total
Oct 19 - Oct 20
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
P32,826
P41,052 total
Oct 22 - Oct 23
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 Keyโ€”home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

See all hotels in Upper Matecumbe Key
A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top Upper Matecumbe Key Hotel Reviews

Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"We love staying at Hawks Cay we have been going for years. The Property amenities are amazing. However, the Villa we stayed at (7039) was in horrible condition. Roaches in kitchen and bathroom, Shades on windows were broken in rooms. The jacuzzi outside was dirty and we were not able to use. We were extremely disappointed to have found it in that condition. I reported to the front office when we checked out. I didn't bother saying anything while there because I am pretty sure they didn't have another one available."
Ivonne 3-night trip
Posted 16 hours ago
Hawks Cay Resort

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