Book The Best Hotels in Upper Matecumbe Key, FL for 2026 from CA $134 - Fully Refundable Options

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

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Go beyond your typical stay in Upper Matecumbe Key

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Our top choices for Upper Matecumbe Key hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

A tropical resort with a swimming pool, palm trees, and a waterfall.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

CA $194

CA $322 total

includes taxes & fees

Oct 4 - Oct 5

A beach with palm trees and lounge chairs.

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

2. Chesapeake Beach Resort

Matecumbe

Suresh

CA $198

CA $303 total

includes taxes & fees

Sep 30 - Oct 1

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A wooden pier leading to a beach with palm trees and a row of beach huts.

A paved pathway leading to a beach with palm trees and a view of the ocean.

A bar area with a wooden counter, bar stools, and potted plants.

3. Islander Resort

Matecumbe

John

CA $304

CA $446 total

includes taxes & fees

Sep 29 - Sep 30

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

A beachfront property with a white building, a balcony with a white railing, and palm trees.

4. La Jolla Resort

Matecumbe

Leslie

CA $125

CA $180 total

includes taxes & fees

Sep 29 - Sep 30

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 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.

An aerial view of a resort with a swimming pool, palm trees, and a dock.

5. Amara Cay Resort

Matecumbe

MICHAEL

CA $201

CA $330 total

includes taxes & fees

Sep 29 - Sep 30

A balcony with a view of a beach, a pool, and a thatched-roof structure.

An aerial view of a marina with docked boats, a building with balconies, and a beach area.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

6. Hadley Resort and Marina

Matecumbe

weder

CA $167

CA $234 total

includes taxes & fees

Sep 28 - Sep 29

A beach with palm trees, thatched-roof huts, and lounge chairs.

A living room with a sofa, armchair, coffee table, and lamp. There is a dining area with a table and chairs. The room has a kitchen area with a stove and cabinets.

A beach with thatched umbrellas, palm trees, and lounge chairs.

A building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.

7. Breezy Palms Resort

Matecumbe

Debra

CA $116

CA $153 total

includes taxes & fees

Sep 29 - Sep 30

A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

A coastal resort with a marina, clear blue water, and lush greenery.

A beachside resort with a pool area, lounge chairs, and palm trees.

A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

8. Pines & Palms Resort

Matecumbe

Colt

CA $279

CA $392 total

includes taxes & fees

Oct 1 - Oct 2

A beachside lounge with a wooden deck, thatched roof, and tropical plants.

A waterfront property with a paved walkway, palm trees, and a white building with a dock.

A bar area with a counter, stools, and potted plants.

9. Bayside Villas by Islander Resort

Matecumbe

beata

CA $349

CA $496 total

includes taxes & fees

Sep 29 - Sep 30

An aerial view of a resort with a swimming pool, lounge chairs, and palm trees.

A view from a window overlooking a beach with palm trees and a wooden pier.

10. Casa Morada

Matecumbe

David

CA $224

CA $268 total

includes taxes & fees

Oct 6 - Oct 7

A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

A beach with an American flag, palm trees, and a barbecue area.

A two-story building with a balcony, surrounded by palm trees and a sandy ground.

A compact, well-lit room with a bed, bedside table, and a small seating area.

11. Sands of Islamorada

Matecumbe

Nicolas

CA $272

CA $325 total

includes taxes & fees

Oct 1 - Oct 2

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

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.

A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

12. The Islands of Islamorada

Matecumbe

Christian

CA $573

CA $734 total

includes taxes & fees

Oct 1 - Oct 2

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

A hotel room with two beds, a TV, a desk with a chair, and a balcony with a view of greenery.

A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

13. Fisher Inn Resort & Marina

Islamorada

Alexandra

CA $179

CA $248 total

includes taxes & fees

Sep 28 - Sep 29

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.

A coastal resort with a beach, a swimming pool, and multiple buildings.

A resort with a pool, beach, and ocean view.

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

Islamorada

Eslita

CA $293

CA $433 total

includes taxes & fees

Oct 6 - Oct 7

A beachside patio with white furniture, palm trees, and a thatched umbrella.

A pool area with lounge chairs and a sign indicating a drop-off zone.

A deck with white lounge chairs and a bench, overlooking a beach with palm trees and a thatched roof structure.

A beach with palm trees, a thatched umbrella, and lounge chairs.

15. Drop Anchor

Islamorada

Payman

CA $179

CA $251 total

includes taxes & fees

Sep 29 - Sep 30

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

A beach with palm trees, a thatched-roof hut, and lounge chairs.

A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.

A beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

16. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

CA $192

CA $216 total

includes taxes & fees

Sep 27 - Sep 28

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

A beach with palm trees, lounge chairs, and a view of the ocean.

A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

17. Rock Reef Resort

Rock Harbor

Tia

CA $131

CA $147 total

includes taxes & fees

Sep 27 - Sep 28

A beach with rows of sun loungers and palm trees.

Three Adirondack chairs facing a sunset over a body of water.

A marina with a boat docked at a wooden pier, surrounded by palm trees and buildings.

A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

18. Ragged Edge Resort & Marina

Islamorada

Nathalie

CA $198

CA $222 total

includes taxes & fees

Sep 29 - Sep 30

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

A kitchen with white cabinets, a microwave, a stove, and a refrigerator.

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

A boat with a covered deck, metal railings, and a table with chairs.

19. Treasure Harbor

Islamorada

Molly

CA $151

CA $369 total

includes taxes & fees

Sep 28 - Sep 29

A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

A beach view with palm trees and a thatched-roof structure.

20. Matecumbe Resort

Matecumbe

Adrian

CA $182

CA $205 total

includes taxes & fees

Sep 27 - Sep 28

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Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

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Florida Keys Brewing Co.

9.2/10 (520 reviews)

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

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A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

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Islamorada Brewery & Distillery

9.4/10 (8 reviews)

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

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Lorelei Restaurant & Cabana Bar

After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.

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MoradaWay Arts & Cultural District

Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.

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beach near Islamorada

Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?

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Keys History & Discovery Center

You can spend time exploring the galleries in Keys History & Discovery Center during your trip to 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 Lorelei Restaurant & Cabana Bar.

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

8/10 Good

"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."

Waterside Suites & Marina

8/10 Good

"Comfortable bed, clean . It’s off the busy road and close to restaurants"

Chesapeake Beach Resort

8/10 Good

"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"

Casa Morada

10/10 Excellent

"always a favorite!"

Lime Tree Bay Resort

10/10 Excellent

"Very lovely stay, everyone who worked there was super friendly!"

La Jolla Resort

8/10 Good

"Loved the amenities"

Hawks Cay Resort

10/10 Excellent

"The resort was beautiful. The food was good but pricey. We loved having the option to have the food/drinks delivered by the pool. The bed was comfortable and the Cabana room was very convenient to have right next to the adult pool area. Our only issue was the AC fluctuated a bit and a few nights it got too cold (one of our neighbors room was way too warm so it could have been worse). And the hot water wasn't really hot enough to take a decent shower. But overall we felt these were minor issues and the staff was so amazing we felt well taken care of otherwise."

Bayside Inn Key Largo

10/10 Excellent

"Great location !!"

The Pelican Key Largo Cottages

10/10 Excellent

"The place had character and culture that modern sterile resorts do not."

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

CA $119

CA $134 total

Sep 27 - Sep 28

includes taxes & fees

9/10 Wonderful! (1,004 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

CA $131

CA $147 total

Sep 27 - Sep 28

includes taxes & fees

9.2/10 Wonderful! (1,188 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

CA $116

CA $153 total

Sep 29 - Sep 30

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

CA $160

CA $180 total

Oct 3 - Oct 4

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

CA $168

CA $189 total

Oct 6 - Oct 7

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

CA $202

CA $228 total

Sep 27 - Sep 28

includes taxes & fees

7.8/10 Good! (1,020 reviews)

Hotels in Upper Matecumbe Key with star rating

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from CA $134

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upper Matecumbe Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Upper Matecumbe Key hotels

1. Cheeca Lodge & Spa

2. Chesapeake Beach Resort

3. Islander Resort

4. La Jolla Resort

5. Amara Cay Resort

6. Hadley Resort and Marina

7. Breezy Palms Resort

8. Pines & Palms Resort

9. Bayside Villas by Islander Resort

10. Casa Morada

11. Sands of Islamorada

12. The Islands of Islamorada

13. Fisher Inn Resort & Marina

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

15. Drop Anchor

16. Coconut Cove Resort and Marina

17. Rock Reef Resort

18. Ragged Edge Resort & Marina

19. Treasure Harbor

20. Matecumbe Resort

Stay near popular Upper Matecumbe Key attractions

Bud n' Mary's Dive Center

Florida Keys Brewing Co.

History of Diving Museum

Islamorada Brewery & Distillery

Lorelei Restaurant & Cabana Bar

MoradaWay Arts & Cultural District

beach near Islamorada

Keys History & Discovery Center

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Waterside Suites & Marina

Chesapeake Beach Resort

Casa Morada

Lime Tree Bay Resort

La Jolla Resort

Hawks Cay Resort

Bayside Inn Key Largo

The Pelican Key Largo Cottages

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

Breezy Palms Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Hotels in Upper Matecumbe Key with star rating

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