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 $319

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 4 Star Hotels

Tonight
Sep 9 - Sep 10
Tomorrow
Sep 10 - Sep 11
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Upper Matecumbe Key 4-star hotels

A hammock on a sandy beach with a view of the sea and a tree overhead.
A spacious interior with a high ceiling, large windows, and a central chandelier.
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 table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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
Milagros
CA $327
CA $443 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 beach with palm trees, a dock, and lounge chairs.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.
A resort pool with palm trees, beach chairs, and umbrellas.

2. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Amy
CA $196
CA $321 total
includes taxes & fees
Sep 16 - Sep 17
Amara Cay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.
A coastal resort with a beach, a swimming pool, and multiple buildings.
A resort with a pool, beach, and ocean view.
A beach with palm trees, a clear blue sky, and a calm sea.

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Ana
CA $253
CA $385 total
includes taxes & fees
Sep 15 - Sep 16
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.

4. Hawks Cay Resort

Hawks Cay Resort
Marathon
United States
Clara
CA $189
CA $319 total
includes taxes & fees
Sep 16 - Sep 17
Hawks Cay Resort
An aerial view of a resort with a large pool, palm trees, and a beach.
A restaurant with wooden tables and chairs, a bar area, and a view of the sea.
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.

5. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Rachel
CA $351
CA $471 total
includes taxes & fees
Sep 22 - Sep 23
Playa Largo Resort & Spa, Autograph Collection
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.

6. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
CA $270
CA $397 total
includes taxes & fees
Sep 16 - Sep 17
Islander Resort
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 resort with a pool surrounded by palm trees and a view of the ocean.

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 resort with a large pool surrounded by lounge chairs, a beach area, and a building with multiple floors.
A modern kitchen with white cabinetry, a stainless steel oven, and a large island with a bowl of fruit.

8. Villas At Hawks Cay Resort

Villas At Hawks Cay Resort
Marathon
United States
Don
CA $522
CA $673 total
includes taxes & fees
Sep 15 - Sep 16
Villas At Hawks Cay Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
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
CA $554
CA $710 total
includes taxes & fees
Oct 1 - Oct 2
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 restaurant with a bar area, wooden ceiling, large windows, and potted plants.
A clear blue pool with lounge chairs and umbrellas, surrounded by greenery.

10. 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 living room with a sofa, armchair, and coffee table, a dining area with a table and chairs, and a kitchen in the background.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

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 a central island, bar stools, and a ceiling fan.
A modern kitchen with white cabinets, a microwave, and a dishwasher. There are three bar stools and a large window overlooking the ocean.

12. Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views
Long Key
Florida Keys Getaway w/ Stunning Ocean Views
Save an average of 15% on thousands of hotels when you're signed in

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 $198
CA $324 total
Oct 4 - Oct 5
includes taxes & fees
Cheeca Lodge & Spa
Still don't see what you're looking for?
See all properties in Upper Matecumbe Key.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Islamorada Brewery & Distillery and Bud n' Mary's Dive Center.

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

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Encantada"
Franklin 2-night trip
Posted 2 hours ago
La Siesta Resort & Villas
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"Amazing"
Leilanis 1-night trip
Posted 15 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"We loved the place"
Badoglio Urbano 2-night trip
Posted 1 day ago
Hawks Cay Resort
Islander Resort

Islander Resort

10/10 Excellent
"Everything is super great beside Beach If you looking to swim in the ocean not best pick"
Rostyslav 2-night trip
Posted 1 day ago
Islander 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.

Explore a world of travel with Expedia