𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Upper Matecumbe Key from S$110 (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 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 waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

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

1. Chesapeake Beach Resort

Matecumbe

Richard

S$272

includes taxes & fees

14 Oct - 15 Oct

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 resort pool with palm trees, beach chairs, and umbrellas.

A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

2. Amara Cay Resort

Matecumbe

Danielle

S$301

includes taxes & fees

20 Oct - 21 Oct

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

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.

A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

3. Cheeca Lodge & Spa

Matecumbe

Morgan

S$334

includes taxes & fees

21 Oct - 22 Oct

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.

4. La Jolla Resort

Matecumbe

Brett

S$199

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

5. Islander Resort

Matecumbe

Steven

S$428

includes taxes & fees

18 Oct - 19 Oct

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

A beach with thatched umbrellas, palm trees, 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.

6. Breezy Palms Resort

Matecumbe

Gavin

S$162

includes taxes & fees

21 Oct - 22 Oct

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

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

7. Hadley Resort and Marina

Matecumbe

weder

S$248

includes taxes & fees

9 Nov - 10 Nov

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

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

8. Pines & Palms Resort

Matecumbe

Colt

S$317

includes taxes & fees

13 Oct - 14 Oct

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.

9. La Siesta Resort & Villas

Matecumbe

Brianne

S$336

includes taxes & fees

8 Nov - 9 Nov

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

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

10. Bayside Villas by Islander Resort

Matecumbe

Brian

S$467

includes taxes & fees

19 Oct - 20 Oct

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

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

11. Sands of Islamorada

Matecumbe

Nicolas

S$294

includes taxes & fees

13 Oct - 14 Oct

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

S$836

includes taxes & fees

13 Oct - 14 Oct

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.

13. Casa Morada

Matecumbe

David

S$245

includes taxes & fees

28 Oct - 29 Oct

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

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

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

14. Lime Tree Bay Resort

Long Key

Michael

S$236

includes taxes & fees

13 Oct - 14 Oct

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

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

A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

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

15. Rock Reef Resort

Rock Harbor

Tia

S$110

includes taxes & fees

27 Oct - 28 Oct

A bathroom with a white sink, a toilet, a bathtub with a shower curtain, a mirror with lights, and a shelf with towels.

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

16. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

Omar Ahmad

S$182

includes taxes & fees

14 Oct - 15 Oct

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

A modern living room with a dark brown sofa, a coffee table, and a blue lamp. There is a kitchen area with a microwave and a coffee machine. A painting of a beach scene is on the wall.

A tree with string lights, a wooden bench, and a building in the background.

A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

17. Drift Hotel

Key Largo

kelly

S$180

includes taxes & fees

13 Oct - 14 Oct

A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

A modern kitchen with wooden cabinets, a central island with stools, and a ceiling fan.

A waterfront property with a large building, a dock, lounge chairs, and a thatched-roof area.

A beach with a row of palm trees, a rocky breakwater, and boats on the water.

18. Dolphin Point Villas

Key Largo

Ernest

S$196

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

19. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

S$215

includes taxes & fees

26 Oct - 27 Oct

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.

20. Ragged Edge Resort & Marina

Islamorada

Nathalie

S$174

includes taxes & fees

18 Oct - 19 Oct

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Hotels recommended for families in Upper Matecumbe Key

Cheeca Lodge & Spa

Matecumbe

S$334

includes taxes & fees

21 Oct - 22 Oct

La Jolla Resort

Matecumbe

S$199

includes taxes & fees

19 Oct - 20 Oct

Breezy Palms Resort

Matecumbe

S$162

includes taxes & fees

21 Oct - 22 Oct

Amara Cay Resort

Matecumbe

S$301

includes taxes & fees

20 Oct - 21 Oct

Islander Resort

Matecumbe

S$428

includes taxes & fees

18 Oct - 19 Oct

Hadley Resort and Marina

Matecumbe

S$248

includes taxes & fees

9 Nov - 10 Nov

La Siesta Resort & Villas

Matecumbe

S$336

includes taxes & fees

8 Nov - 9 Nov

Pines & Palms Resort

Matecumbe

S$317

includes taxes & fees

13 Oct - 14 Oct

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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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A stone monument with a relief sculpture, surrounded by palm trees and a clear blue sky.

Hurricane Monument

8.6/10 (250 reviews)

The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.

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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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MoradaWay Arts & Cultural District

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

A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top Upper Matecumbe Key Hotel Reviews

Waterside Suites & Marina

10/10 Excellent

"Easy checkin. Good pool. Balconies overlook an inlet with docked boats. Saw a lot of fish swimming, as well as divers taking lessons."

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

10/10 Excellent

"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"

Hawks Cay Resort

10/10 Excellent

"Clean villas and very nice. Pool was great and the breakfast and tiki bar were nice. Staff were solid, but not amazing or over the top by any means which is fine for me but maybe not others. For example, took an hour and a second call to get towels because we were short one for someone to take a shower. Lots of cones on the roads and work going on but it is the off-season so they have to get it done at one point! Overall we had a great time!"