Upper Matecumbe Key Hotel & Accommodation Deals 2026 from AU$133 - Compare prices by date

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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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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

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

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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

AU$318

includes taxes & fees

29 Sept - 30 Sept

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

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

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 white building, a balcony with a white railing, and palm trees.

2. La Jolla Resort

Matecumbe

Tamara

AU$211

includes taxes & fees

22 Sept - 23 Sept

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

A wooden pier leading to a beach with palm trees and a row of beach huts.

3. Islander Resort

Matecumbe

Sonia

AU$434

includes taxes & fees

29 Sept - 30 Sept

A beach with palm trees and lounge chairs.

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.

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

4. Chesapeake Beach Resort

Matecumbe

Suresh

AU$308

includes taxes & fees

24 Sept - 25 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.

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.

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

5. Amara Cay Resort

Matecumbe

Amy

AU$325

includes taxes & fees

22 Sept - 23 Sept

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

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.

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

6. Hadley Resort and Marina

Matecumbe

RAIBEL

AU$245

includes taxes & fees

16 Sept - 17 Sept

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.

7. Breezy Palms Resort

Matecumbe

Lourdes

AU$152

includes taxes & fees

21 Sept - 22 Sept

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.

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

AU$385

includes taxes & fees

30 Sept - 1 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 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.

9. Pines & Palms Resort

Matecumbe

Stephen

AU$359

includes taxes & fees

16 Sept - 17 Sept

A balcony with a wooden table, two chairs, and a view of the ocean 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.

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

10. The Islands of Islamorada

Matecumbe

Christian

AU$724

includes taxes & fees

16 Sept - 17 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.

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

11. Casa Morada

Matecumbe

Lois

AU$265

includes taxes & fees

7 Oct - 8 Oct

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 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.

12. Sands of Islamorada

Matecumbe

Virginia

AU$303

includes taxes & fees

16 Sept - 17 Sept

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 beach with palm trees, a clear blue sky, and a calm sea.

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

Islamorada

Eslita

AU$389

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

14. Fisher Inn Resort & Marina

Islamorada

Alexandra

AU$232

includes taxes & fees

21 Sept - 22 Sept

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

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

A pool area with lounge chairs and a sign indicating a drop-off zone.

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

15. Drop Anchor

Islamorada

Marianela

AU$216

includes taxes & fees

16 Sept - 17 Sept

A beach with rows of sun loungers and palm trees.

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.

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

16. Ragged Edge Resort & Marina

Islamorada

Marianne

AU$133

includes taxes & fees

20 Sept - 21 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 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.

17. Coconut Cove Resort and Marina

Islamorada

Jasmine

AU$234

includes taxes & fees

17 Sept - 18 Sept

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

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

18. Rock Reef Resort

Rock Harbor

Tia

AU$158

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

A pool area with a white fence, a lifebuoy, and palm trees in the background.

A boat with a covered deck, metal railings, and a table with chairs.

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

19. Treasure Harbor

Islamorada

Molly

AU$378

includes taxes & fees

13 Oct - 14 Oct

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

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

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.

20. Drift Hotel

Key Largo

Sheily

AU$163

includes taxes & fees

17 Sept - 18 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 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 studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.

See properties

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 beachside café with colorful chairs and tables, palm trees, and a view of the ocean.

Top Upper Matecumbe Key Hotel Reviews

Recent Reviews in Upper Matecumbe Key

Breezy Palms Resort

10/10 Excellent

"Great place... it is not fancy but it is comfortable, spacious, pool is clean, well located.... I can come back anytime"

Playa Largo Resort & Spa, Autograph Collection

8/10 Good

"Lovely hotel. Very expensive just to buy drinks though but good location."

Cheeca Lodge & Spa

10/10 Excellent

"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained."

Lime Tree Bay Resort

10/10 Excellent

"We have been coming here since 2018 and it never fails us we enjoy staying here for a whole week. The first time around we extended our stay and have been staying for a week since. Hands down to Terri O., she’s my go to for when we plan our next family vacation she takes care of us always. We shall be planning our next family vacation soon!!"

Hawks Cay Resort

8/10 Good

"Just returned from Hawks Cay, we loved the property in general. The big pool, the lagoon, the outdoor spaces all well maintained. It was our first time here and we appreciated the modern decoration of the lobby and all the areas around it, the breakfast cafe and the restaurant . We stayed at the Pool Cabana room, perfect location in front of the main pool. The room was spacious , with a mini fridge and a coffee maker. Good lighting and space to store your things. My only suggestion would be to improve the beddings and mattresses. Overall I got the feeling of a good old time American resort. Perfect for families since the kids can be at the pool, or kayaking at the lagoon or even fishing. We recommend it 👍"

Islander Resort

10/10 Excellent

"Great location. Very good CLEANING staff and FRONT DESK staff are excellent"

Waterside Suites & Marina

10/10 Excellent

"1"

Chesapeake Beach Resort

10/10 Excellent

"/"

Amara Cay Resort

10/10 Excellent

"Beautiful lobby, nice outdoor area, room is clean, the elevator is a bit old though. Pool is very big, kids love it."

More cheap accommodation in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

AU$144

30 Sept - 1 Oct

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

AU$155

17 Sept - 18 Sept

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

AU$158

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,185 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$205

22 Sept - 23 Sept

includes taxes & fees

8.8/10 Excellent! (1,085 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$207

27 Sept - 28 Sept

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

AU$253

28 Sept - 29 Sept

includes taxes & fees

Explore a world of travel with Expedia

Car hire near Kendall

Book Hotels in Upper Matecumbe Key on Expedia.com

Search Upper Matecumbe Key hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upper Matecumbe Key

Check prices for these dates

Filter by

Property class

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. Bayside Villas by Islander Resort

9. Pines & Palms Resort

10. The Islands of Islamorada

11. Casa Morada

12. Sands of Islamorada

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

14. Fisher Inn Resort & Marina

15. Drop Anchor

16. Ragged Edge Resort & Marina

17. Coconut Cove Resort and Marina

18. Rock Reef Resort

19. Treasure Harbor

20. Drift Hotel

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

Recent Reviews in Upper Matecumbe Key

Breezy Palms Resort

Playa Largo Resort & Spa, Autograph Collection

Cheeca Lodge & Spa

Lime Tree Bay Resort

Hawks Cay Resort

Islander Resort

Waterside Suites & Marina

Chesapeake Beach Resort

Amara Cay Resort

More cheap accommodation in Upper Matecumbe Key

The Pelican Key Largo Cottages

Sunset Cove Beach Resort

Rock Reef Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

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