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

4 Stars Hotels in Upper Matecumbe Key, Islamorada from CA $332

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Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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
juan
CA $396
CA $524 total
includes taxes & fees
Oct 20 - Oct 21
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.
A pathway leading to a pool area with palm trees and a sunset view.
A modern living room with a balcony overlooking the sea, furnished with a sofa, chairs, and a dining table.

2. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Katherine
CA $288
CA $433 total
includes taxes & fees
Oct 18 - Oct 19
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 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
Danielle
CA $203
CA $332 total
includes taxes & fees
Oct 18 - Oct 19
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 resort with a pool, beach, and ocean view.

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
CA $326
CA $471 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 wooden pier leading to a beach with palm trees and a row of beach huts.

5. Islander Resort

Islander Resort
Matecumbe
United States
Steven
CA $335
CA $481 total
includes taxes & fees
Oct 20 - Oct 21
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 beach with clear water, a wooden pier, and lounge chairs under a tree.

6. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Tania
CA $375
CA $500 total
includes taxes & fees
Nov 1 - Nov 2
Playa Largo Resort & Spa, Autograph Collection
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
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.
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
CA $240
CA $374 total
includes taxes & fees
Nov 8 - Nov 9
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 resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.
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
CA $783
CA $969 total
includes taxes & fees
Oct 30 - Oct 31
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 wooden deck with a thatched-roof structure, a sign indicating no swimming, and a clear view of the ocean.
A restaurant with a bar area, wooden ceiling, large windows, and potted plants.

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 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.

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 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 beach with clear turquoise water, a wooden pier, and a rocky shoreline.

11. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
Florida Keys Getaway w/ Stunning Ocean Views
Property grounds
Pool
Beach/ocean view
Private kitchen

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
CA $238
CA $372 total
Oct 22 - Oct 23
includes taxes & fees
Cheeca Lodge & Spa
The Islands of Islamorada

The Islands of Islamorada

82779 Old Hwy Islamorada FL
CA $685
CA $863 total
Oct 18 - Oct 19
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 shark sculpture with a sign above it that reads "Islamorada Florida Keys".

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
"This place was beautiful and relaxing. The staff was amazing and the beds are super comfortable. We also enjoyed the pools and beach area as well as the Dry Rocks restaurant where the food was wonderful! I would absolutely stay again!"
Jason 1-night trip
Posted 6 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"
Maureen 2-night trip
Posted 4 days ago
Amara Cay Resort

Find out more about Upper Matecumbe Key

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Upper Matecumbe Key are calling your name. Known for providing first-rate service in amazing locations, each of the Upper Matecumbe Key 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Upper Matecumbe Key. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Upper Matecumbe Key, Islamorada, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Upper Matecumbe Key hotels with 4 Stars provide everything you need to unwind in style.

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