𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Upper Matecumbe Key from RM403 (2026) - 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 spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

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.

1. Cheeca Lodge & Spa

Matecumbe

Mian

RM600

RM969 total

includes taxes & fees

7 Sept - 8 Sept

A beach with palm trees and lounge chairs.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

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

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

2. Chesapeake Beach Resort

Matecumbe

Suresh

RM608

RM910 total

includes taxes & fees

7 Sept - 8 Sept

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

3. Islander Resort

Matecumbe

Sonia

RM983

RM1,377 total

includes taxes & fees

22 Sept - 23 Sept

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.

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.

4. Amara Cay Resort

Matecumbe

David A

RM595

RM964 total

includes taxes & fees

3 Sept - 4 Sept

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

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

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

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

5. La Jolla Resort

Matecumbe

adrian

RM476

RM649 total

includes taxes & fees

2 Sept - 3 Sept

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

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

6. Pines & Palms Resort

Matecumbe

Isabel

RM641

RM943 total

includes taxes & fees

2 Sept - 3 Sept

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

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

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

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

7. Hadley Resort and Marina

Matecumbe

RAIBEL

RM467

RM657 total

includes taxes & fees

20 Sept - 21 Sept

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

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

A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

8. Bayside Villas by Islander Resort

Matecumbe

beata

RM788

RM1,159 total

includes taxes & fees

14 Sept - 15 Sept

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

A beach with colorful buildings, kayaks, and lounge chairs.

A resort with a pool surrounded by palm trees and a view of the ocean.

A row of colorful beach huts with palm trees in the background.

9. La Siesta Resort & Villas

Matecumbe

Brianne

RM595

RM964 total

includes taxes & fees

3 Sept - 4 Sept

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 beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

A pool area with clear blue water, white lounge chairs, and palm trees.

10. The Islands of Islamorada

Matecumbe

Christian

RM1,449

RM1,881 total

includes taxes & fees

2 Sept - 3 Sept

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

11. Breezy Palms Resort

Matecumbe

Orlando

RM366

RM620 total

includes taxes & fees

6 Sept - 7 Sept

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.

12. Casa Morada

Matecumbe

Lois

RM667

RM795 total

includes taxes & fees

7 Sept - 8 Sept

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.

13. Sands of Islamorada

Matecumbe

Virginia

RM774

RM926 total

includes taxes & fees

2 Sept - 3 Sept

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

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

Islamorada

Dareen

RM705

RM1,088 total

includes taxes & fees

7 Sept - 8 Sept

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.

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

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

15. Fisher Inn Resort & Marina

Islamorada

MARC

RM450

RM638 total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

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

16. Drop Anchor

Islamorada

Marianela

RM485

RM687 total

includes taxes & fees

3 Sept - 4 Sept

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

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.

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.

17. The Ocean View Inn & Pub

Islamorada

Patrice

RM750

RM844 total

includes taxes & fees

3 Sept - 4 Sept

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

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

18. Coconut Cove Resort and Marina

Islamorada

Lisa C

RM450

RM506 total

includes taxes & fees

3 Sept - 4 Sept

19. Coconut Palm Inn

Tavernier

judith

RM757

RM1,011 total

includes taxes & fees

2 Sept - 3 Sept

A beach with rows of sun loungers and palm trees.

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.

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

20. Ragged Edge Resort & Marina

Islamorada

Katarzyna

RM359

RM403 total

includes taxes & fees

13 Sept - 14 Sept

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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 family-friendly 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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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 studying the exhibits at Keys History & Discovery Center during your trip to 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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Learn more about Upper Matecumbe Key

Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

8/10 Good

"Amenities and the property are absolutely beautiful. Mixed feelings about the staff. The bartenders and pool waitress get an A+. Everyone else could be friendlier :) No problems getting through the gate, which I've had issues with at other properties. Even when the night guard steps away, they will send security in less than a minute to open the gate for you so that was great. We enjoyed our stay and I would go back."

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 être inclus mais il nous a été facturé ."

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 I’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 label—especially after multiple messages. A little follow-through and basic courtesy would have made a significant difference."

Waterside Suites & Marina

10/10 Excellent

"Rainbow Reef is next door. Huge patio to dry gear. Scuba divers perfect spot!"

Islander Resort

8/10 Good

"Great property with an amazing concept, especially in an area where there aren’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."

Breezy Palms Resort

10/10 Excellent

"The staff was very helpful and it was a great location on the water with boat rentals and other things to do. Overall it was a great experience"

Chesapeake Beach Resort

10/10 Excellent

"Lindo y acogedor lugar, cerca del sandbar con marina para poner tu bote. Nuestra eetancia fue excelente. El staff bien amable y atento. Volveremos Gracias"

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!!!"

La Jolla Resort

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️"

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

RM397

RM447 total

7 Sept - 8 Sept

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Drift Hotel

95320 Overseas Hwy Key Largo FL

RM387

RM480 total

2 Sept - 3 Sept

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

RM500

RM562 total

8 Sept - 9 Sept

includes taxes & fees

7.8/10 Good! (1,020 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

RM525

RM590 total

14 Sept - 15 Sept

includes taxes & fees

8.8/10 Excellent! (1,076 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

RM366

RM620 total

6 Sept - 7 Sept

includes taxes & fees

8.8/10 Excellent! (736 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

RM559

RM743 total

14 Sept - 15 Sept

includes taxes & fees

Upper Matecumbe Key hotels from RM403

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. Amara Cay Resort

5. La Jolla Resort

6. Pines & Palms Resort

7. Hadley Resort and Marina

8. Bayside Villas by Islander Resort

9. La Siesta Resort & Villas

10. The Islands of Islamorada

11. Breezy Palms Resort

12. Casa Morada

13. Sands of Islamorada

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

15. Fisher Inn Resort & Marina

16. Drop Anchor

17. The Ocean View Inn & Pub

18. Coconut Cove Resort and Marina

19. Coconut Palm Inn

20. Ragged Edge Resort & Marina

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

beach near Islamorada

Keys History & Discovery Center

MoradaWay Arts & Cultural District

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

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

Amara Cay Resort

Waterside Suites & Marina

Islander Resort

Breezy Palms Resort

Chesapeake Beach Resort

Hawks Cay Resort

La Jolla Resort

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Drift Hotel

Creekside Inn

Hampton Inn Key Largo Manatee Bay

Breezy Palms Resort

Marina Del Mar Resort and Marina

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