Upper Matecumbe Key Hotels from €92 - Fully Refundable Options

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

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

Go beyond your typical stay in Upper Matecumbe Key

Pet friendly

Villa

Apartment

Spa

Apart hotel

Hot tub

Pool

Condo

Resort

Houseboat

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

€214

includes taxes & fees

4 Oct - 5 Oct

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

2. La Jolla Resort

Matecumbe

Kayla

€122

includes taxes & fees

6 Oct - 7 Oct

A beach with palm trees and lounge chairs.

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.

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

3. Chesapeake Beach Resort

Matecumbe

Suresh

€201

includes taxes & fees

5 Oct - 6 Oct

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

4. Breezy Palms Resort

Matecumbe

Zack

€96

includes taxes & fees

4 Oct - 5 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.

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

5. Amara Cay Resort

Matecumbe

MICHAEL

€220

includes taxes & fees

5 Oct - 6 Oct

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.

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.

6. Hadley Resort and Marina

Matecumbe

weder

€164

includes taxes & fees

18 Oct - 19 Oct

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.

7. Islander Resort

Matecumbe

Steven

€351

includes taxes & fees

27 Oct - 28 Oct

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

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

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

€255

includes taxes & fees

15 Oct - 16 Oct

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

A gated entrance to a resort with palm trees and a clear sky.

9. The Islands of Islamorada

Matecumbe

Christian

€581

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

10. Sands of Islamorada

Matecumbe

Nicolas

€204

includes taxes & fees

12 Oct - 13 Oct

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

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

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

11. Bayside Villas by Islander Resort

Matecumbe

beata

€389

includes taxes & fees

18 Oct - 19 Oct

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

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

12. Casa Morada

Matecumbe

David

€168

includes taxes & fees

7 Oct - 8 Oct

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

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

13. Rock Reef Resort

Rock Harbor

Tia

€101

includes taxes & fees

4 Oct - 5 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 sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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 beach with lounge chairs, kayaks, and a wooden pier.

14. Drift Hotel

Key Largo

kelly

€103

includes taxes & fees

26 Oct - 27 Oct

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.

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

15. Lime Tree Bay Resort

Long Key

Michael

€156

includes taxes & fees

5 Oct - 6 Oct

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

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

A resort with a pool, multiple buildings, and a waterfront 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

€126

includes taxes & fees

8 Oct - 9 Oct

A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

A pathway lined with palm trees and a speed limit sign of 5 MPH.

A sunset over a calm body of water with a dock and lounge chairs.

A bakery display case with various muffins and frittatas labeled with flavors like blueberry, cranberry orange, banana walnut, chocolate, egg cheese vegetable fritta, egg sausage fritta, and egg cheese fritta.

17. Seafarer Key Largo

Rock Harbor

ANDREW

€104

includes taxes & fees

4 Oct - 5 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden 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.

18. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

€149

includes taxes & fees

4 Oct - 5 Oct

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.

19. Fisher Inn Resort & Marina

Islamorada

Siobhan

€156

includes taxes & fees

12 Oct - 13 Oct

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

A marina with docks, lounge chairs, and a clear view of the water.

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.

20. Dolphin Point Villas

Key Largo

Ernest

€148

includes taxes & fees

4 Oct - 5 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

Florida Keys Brewing Co.

9.2/10 (520 reviews)

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

See properties

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.

See properties