Upper Matecumbe Key Hotel & Accommodation Deals 2026 from NZ$184 - 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

Suresh

NZ$382

includes taxes & fees

5 Oct - 6 Oct

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 hotel room with a large bed, a television, a dining area with chairs, a table, 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.

2. Cheeca Lodge & Spa

Matecumbe

RAIBEL

NZ$406

includes taxes & fees

4 Oct - 5 Oct

A compact hotel room with a kitchenette, a bed with a wooden headboard, a painting of the ocean, and a potted plant.

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

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.

3. La Jolla Resort

Matecumbe

Kayla

NZ$244

includes taxes & fees

6 Oct - 7 Oct

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

A beach with thatched umbrellas, palm trees, 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 modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

4. Breezy Palms Resort

Matecumbe

Zack

NZ$193

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

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

A beach with palm trees, a dock, and lounge chairs.

5. Amara Cay Resort

Matecumbe

MICHAEL

NZ$425

includes taxes & fees

5 Oct - 6 Oct

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 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.

6. Islander Resort

Matecumbe

Steven

NZ$679

includes taxes & fees

21 Oct - 22 Oct

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.

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

7. Hadley Resort and Marina

Matecumbe

weder

NZ$330

includes taxes & fees

18 Oct - 19 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 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.

8. Pines & Palms Resort

Matecumbe

Colt

NZ$458

includes taxes & fees

3 Oct - 4 Oct

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

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.

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

9. Sands of Islamorada

Matecumbe

Nicolas

NZ$410

includes taxes & fees

12 Oct - 13 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 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.

10. The Islands of Islamorada

Matecumbe

Christian

NZ$1,085

includes taxes & fees

22 Oct - 23 Oct

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

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.

11. Bayside Villas by Islander Resort

Matecumbe

beata

NZ$781

includes taxes & fees

18 Oct - 19 Oct

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

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

12. Casa Morada

Matecumbe

David

NZ$338

includes taxes & fees

7 Oct - 8 Oct

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

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.

13. Lime Tree Bay Resort

Long Key

Michael

NZ$312

includes taxes & fees

5 Oct - 6 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 pool area with a view of the ocean, surrounded by palm trees and a clear sky.

14. Rock Reef Resort

Rock Harbor

Tia

NZ$203

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

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

15. Drift Hotel

Key Largo

kelly

NZ$206

includes taxes & fees

7 Oct - 8 Oct

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

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

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

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

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

Key Largo

Omar Ahmad

NZ$255

includes taxes & fees

6 Oct - 7 Oct

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

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.

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

17. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

NZ$272

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

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

18. Fisher Inn Resort & Marina

Islamorada

Siobhan

NZ$330

includes taxes & fees

7 Oct - 8 Oct

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

A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

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

19. Seafarer Key Largo

Rock Harbor

ANDREW

NZ$209

includes taxes & fees

4 Oct - 5 Oct

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

A waterfront pier with wooden posts and a wooden walkway extending into the water.

A garden with various trees and a gravel path.

A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.

20. Sunset Cove Beach Resort

Key Largo

Payton

NZ$235

includes taxes & fees

12 Oct - 13 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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