Upper Matecumbe Key Hotel & Accommodation Deals 2026 from AU$122 - 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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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 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.

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

1. Cheeca Lodge & Spa

Matecumbe

Mian

AU$336

includes taxes & fees

9 Sept - 10 Sept

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 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

AU$260

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 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$381

includes taxes & fees

22 Sept - 23 Sept

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

adrian

AU$251

includes taxes & fees

4 Sept - 5 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 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.

5. Amara Cay Resort

Matecumbe

Amy

AU$325

includes taxes & fees

14 Sept - 15 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.

6. Breezy Palms Resort

Matecumbe

Orlando

AU$140

includes taxes & fees

7 Sept - 8 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 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.

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

7. Pines & Palms Resort

Matecumbe

Isabel

AU$386

includes taxes & fees

9 Sept - 10 Sept

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.

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.

8. Hadley Resort and Marina

Matecumbe

RAIBEL

AU$254

includes taxes & fees

23 Sept - 24 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.

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

9. Bayside Villas by Islander Resort

Matecumbe

beata

AU$417

includes taxes & fees

15 Sept - 16 Sept

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

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

10. La Siesta Resort & Villas

Matecumbe

Brianne

AU$345

includes taxes & fees

7 Sept - 8 Sept

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

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.

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

11. The Islands of Islamorada

Matecumbe

Christian

AU$698

includes taxes & fees

17 Sept - 18 Sept

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

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

12. Casa Morada

Matecumbe

Lois

AU$276

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 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.

13. Sands of Islamorada

Matecumbe

Virginia

AU$320

includes taxes & fees

1 Oct - 2 Oct

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

Ana

AU$390

includes taxes & fees

10 Sept - 11 Sept

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

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

Two people relaxing on sun loungers by a poolside with a view of the ocean and palm trees in the background.

A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

15. Fisher Inn Resort & Marina

Islamorada

MARC

AU$241

includes taxes & fees

23 Sept - 24 Sept

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

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.

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

16. Coconut Cove Resort and Marina

Islamorada

Lisa C

AU$213

includes taxes & fees

15 Sept - 16 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.

A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

17. Ragged Edge Resort & Marina

Islamorada

Katarzyna

AU$122

includes taxes & fees

13 Sept - 14 Sept

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.

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

18. Lime Tree Bay Resort

Long Key

Chadwick

AU$239

includes taxes & fees

7 Sept - 8 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.

19. Drop Anchor

Islamorada

Marianela

AU$323

includes taxes & fees

7 Sept - 8 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 bedroom with a bed, a nightstand, a chair, and a door.

A bathroom with a sink, toilet, and shower. There is a mirror above the sink and a shelf with towels.

A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

20. The Ocean View Inn & Pub

Islamorada

Patrice

AU$292

includes taxes & fees

7 Sept - 8 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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MoradaWay Arts & Cultural District

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

Recent Reviews in Upper Matecumbe Key

Lime Tree Bay Resort

10/10 Excellent

"Fantastic place to stay. Small family style resort. Old school flordia feel."

Waterside Suites & Marina

8/10 Good

"The room was okay. Nothing stood out about it. I didn't realize the bedroom was on the 2nd floor, and the steps are kind of narrow and steep. Maintenance could repair the blinds."

Pines & Palms Resort

10/10 Excellent

"Quiet, Matthew and JJ were extremely friendly and respectful. Thank you."

Chesapeake Beach Resort

10/10 Excellent

"A great place to stay and very well located. Breakfast staff was wonderful and very accommodating. Check in staff as well. A beautiful property,"

Amara Cay Resort

10/10 Excellent

"Baseboard were removed off the wall. Did not gave it a clean look . Walls in the hallway slightly dirty."

Islander Resort

8/10 Good

"In stay, so many activities near by"

Breezy Palms Resort

10/10 Excellent

"Espectacular y muy limpio"

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"Perfection!"

La Jolla Resort

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️"

More cheap accommodation in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

AU$149

23 Sept - 24 Sept

includes taxes & fees

9/10 Wonderful! (1,006 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

AU$171

13 Sept - 14 Sept

includes taxes & fees

9.2/10 Wonderful! (1,173 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

AU$182

8 Sept - 9 Sept

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$205

14 Sept - 15 Sept

includes taxes & fees

8.8/10 Excellent! (1,078 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$207

7 Sept - 8 Sept

includes taxes & fees

7.8/10 Good! (1,017 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

AU$253

23 Sept - 24 Sept

includes taxes & fees

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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. Chesapeake Beach Resort

3. Islander Resort

4. La Jolla Resort

5. Amara Cay Resort

6. Breezy Palms Resort

7. Pines & Palms Resort

8. Hadley Resort and Marina

9. Bayside Villas by Islander Resort

10. La Siesta Resort & Villas

11. The Islands of Islamorada

12. Casa Morada

13. Sands of Islamorada

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

15. Fisher Inn Resort & Marina

16. Coconut Cove Resort and Marina

17. Ragged Edge Resort & Marina

18. Lime Tree Bay Resort

19. Drop Anchor

20. The Ocean View Inn & Pub

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

MoradaWay Arts & Cultural District

Keys History & Discovery Center

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Recent Reviews in Upper Matecumbe Key

Lime Tree Bay Resort

Waterside Suites & Marina

Pines & Palms Resort

Chesapeake Beach Resort

Amara Cay Resort

Islander Resort

Breezy Palms Resort

Playa Largo Resort & Spa, Autograph Collection

La Jolla Resort

More cheap accommodation in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

Go further with the Expedia app