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
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Upper Matecumbe Key 4-star hotels

A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A modern living room with a balcony overlooking the sea, furnished with a sofa, chairs, and a dining table.
A pathway leading to a pool area with palm trees and a sunset view.
A spacious lobby with high ceilings, large windows, and a central coffee table surrounded by sofas and chairs.

1. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Clara
P11,549
P17,780 total
includes taxes & fees
Sep 13 - Sep 14
Hawks Cay Resort
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.
A spacious interior with a high ceiling, large windows, and a central chandelier.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Vianney
P14,786
P20,075 total
includes taxes & fees
Sep 28 - Sep 29
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 resort pool with palm trees, beach chairs, and umbrellas.
An aerial view of a resort with a swimming pool, palm trees, and a dock.
A beach with palm trees, a dock, and lounge chairs.

3. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
David A
P9,224
P14,939 total
includes taxes & fees
Sep 3 - Sep 4
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.
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.
A wooden pier leading to a beach with palm trees and a row of beach huts.

4. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
P12,214
P17,952 total
includes taxes & fees
Sep 15 - Sep 16
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.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Rachel
P15,877
P21,294 total
includes taxes & fees
Sep 20 - Sep 21
Playa Largo Resort & Spa, Autograph Collection
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.
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.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Dareen
P10,908
P16,825 total
includes taxes & fees
Sep 7 - Sep 8
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 beach resort with palm trees, a thatched hut, and a purple building with a window.
A beach with colorful buildings, kayaks, and lounge chairs.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
P9,624
P15,381 total
includes taxes & fees
Sep 7 - Sep 8
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.
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
Don
P23,598
P30,401 total
includes taxes & fees
Sep 14 - Sep 15
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
P22,415
P29,097 total
includes taxes & fees
Sep 2 - Sep 3
The Islands of Islamorada
A beach with palm trees, lounge chairs, and a thatched-roof structure.
A wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.
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.

10. Condo in the Keys

Condo in the Keys
Tavernier
United States
ann
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 modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.
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.

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 modern kitchen with a central island, bar stools, and a ceiling fan.

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
P9,277
P14,990 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,422 reviews)
Cheeca Lodge & Spa
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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 wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
Photo by Cameron Abbott

Top Upper Matecumbe Key Hotel Reviews

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

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

10/10 Excellent
"Nous n avons pas pris l option petit dej . Le parking devait รชtre inclus mais il nous a รฉtรฉ facturรฉ ."
marc 3-night trip
Posted 11 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

8/10 Good
"The resort is great! I did, however, leave behind my bathing suit and a personal towel hanging on the back of the bathroom door. When I called three days later after realizing they were missing, I learned that housekeeping had set the items aside. I was surprised that no one had contacted me to let me know they had been found. The front desk explained that I would need to provide a prepaid shipping label, which I promptly emailed. I asked for confirmation that the label had been received but received no response. After several days, I followed up again and still heard nothing. My items were eventually returned, and Iโ€™m grateful for that. Overall, I had a nice stay, but the lack of communication was disappointing. A more attentive, customer-focused team would have notified me that the items had been found and acknowledged receipt of the shipping labelโ€”especially after multiple messages. A little follow-through and basic courtesy would have made a significant difference."
Keith 2-night trip
Posted 12 hours ago
Amara Cay Resort
Islander Resort

Islander Resort

8/10 Good
"Great property with an amazing concept, especially in an area where there arenโ€™t many high-end properties offering this style and experience. The facilities are excellent, and overall we really enjoyed our stay. My only negative feedback is that a few members of staff were constantly on their phones watching clips and videos, often with the volume turned up. We found this quite annoying, particularly when trying to relax quietly by the pool. It would be great if staff could be reminded to use headphones or keep phone use to a minimum in guest relaxation areas. Room maintaince could also be better."
Asoka 2-night trip
Posted 17 hours ago
Islander Resort
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"Great place. Loved the area, the staff very helpful and nice. The villa could used a better cleaning but overall was a great stay, will definitely be back!!!"
Clara 3-night trip
Posted 1 day ago
Hawks Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

8/10 Good
"Good"
moraima 3-night trip
Posted 2 days ago
La Siesta Resort & Villas

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