Book The Best Hotels in Upper Matecumbe Key, FL for 2026 from CA $145 - 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 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.

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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

CA $180

CA $306 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

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

2. La Jolla Resort

Matecumbe

Leslie

CA $136

CA $193 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 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.

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

3. Islander Resort

Matecumbe

John

CA $275

CA $405 total

includes taxes & fees

Sep 30 - Oct 1

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.

4. Chesapeake Beach Resort

Matecumbe

Suresh

CA $202

CA $306 total

includes taxes & fees

Oct 5 - Oct 6

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.

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

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.

5. Amara Cay Resort

Matecumbe

MICHAEL

CA $204

CA $333 total

includes taxes & fees

Sep 29 - Sep 30

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

A beach scene with two yellow beach chairs and a person lying on one.

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 $233 total

includes taxes & fees

Sep 28 - Sep 29

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

A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

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 $115

CA $152 total

includes taxes & fees

Oct 4 - Oct 5

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

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

A beach with palm trees, a wooden pier, and beach chairs.

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

8. Pines & Palms Resort

Matecumbe

Colt

CA $278

CA $390 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 $312

CA $446 total

includes taxes & fees

Sep 30 - Oct 1

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

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

A spacious living area with a round dining table, a sofa, and a TV mounted on the wall.

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

10. Sands of Islamorada

Matecumbe

Nicolas

CA $270

CA $323 total

includes taxes & fees

Oct 1 - Oct 2

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

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

11. Casa Morada

Matecumbe

CA $220

CA $264 total

includes taxes & fees

Oct 19 - Oct 20

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 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 $570

CA $730 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

13. Fisher Inn Resort & Marina

Islamorada

Alexandra

CA $178

CA $246 total

includes taxes & fees

Sep 29 - Sep 30

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.

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

Islamorada

Eslita

CA $280

CA $418 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

A wooden boardwalk leading to a building with a brick wall and a white roof.

15. Drop Anchor

Islamorada

Marianela

CA $178

CA $250 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 resort with thatched-roof structures, palm trees, and a sandy beach area.

16. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

CA $205

CA $231 total

includes taxes & fees

Oct 1 - Oct 2

A beach with rows of sun loungers and palm trees.

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

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

A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

17. Ragged Edge Resort & Marina

Islamorada

Nathalie

CA $184

CA $207 total

includes taxes & fees

Sep 27 - Sep 28

A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

A bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, framed artwork on the wall, and an air conditioning unit.

18. The Ocean View Inn & Pub

Islamorada

Maria

CA $262

CA $295 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.

19. Rock Reef Resort

Rock Harbor

Tia

CA $130

CA $147 total

includes taxes & fees

Sep 27 - Sep 28

A beach with palm trees and a clear view of the ocean.

A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

A spacious living area with a large island, wooden furniture, and a ceiling fan.

20. Lime Tree Bay Resort

Long Key

milayda

CA $163

CA $246 total

includes taxes & fees

Sep 28 - Sep 29

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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

Breezy Palms Resort

8/10 Good

"Good"

Bayside Inn Key Largo

10/10 Excellent

"The staff was great very friendly. The place is located really nice beautiful sunset. Had a great time."

Chesapeake Beach Resort

10/10 Excellent

"This facility was clean and well managed. The 2 pools were perfect. The beach area was well maintained. We utilized the free kayaks two days in a row. The breakfast was delicious and had made to order pancakes and omelets. The staff was very friendly. I highly recommend this resort."

Amara Cay Resort

10/10 Excellent

"."

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

10/10 Excellent

"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"

Casa Morada

10/10 Excellent

"Very helpful staff and great location"

Hawks Cay Resort

8/10 Good

"The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel."

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

CA $129

CA $145 total

Oct 1 - Oct 2

includes taxes & fees

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

CA $130

CA $147 total

Sep 27 - Sep 28

includes taxes & fees

9.2/10 Wonderful! (1,187 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

CA $165

CA $185 total

Sep 27 - Sep 28

includes taxes & fees

9.2/10 Wonderful! (1,009 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

CA $183

CA $206 total

Oct 5 - Oct 6

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

CA $201

CA $226 total

Sep 28 - Sep 29

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

CA $190

CA $253 total

Sep 25 - Sep 26

includes taxes & fees

8.6/10 Excellent! (1,870 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 $145

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. La Jolla Resort

3. Islander Resort

4. Chesapeake Beach 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. Sands of Islamorada

11. Casa Morada

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. Ragged Edge Resort & Marina

18. The Ocean View Inn & Pub

19. Rock Reef Resort

20. Lime Tree Bay 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

Breezy Palms Resort

Bayside Inn Key Largo

Chesapeake Beach Resort

Amara Cay Resort

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

Casa Morada

Hawks Cay Resort

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Hotels in Upper Matecumbe Key with star rating

Explore a world of travel with Expedia

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