Top 10 Hotels in Upper Matecumbe Key, FL from ￥16,227 - Competitive Prices

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

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

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

RAIBEL

￥20,170

￥34,202 total

includes taxes & fees

Oct 1 - Oct 2

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

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

2. Islander Resort

Matecumbe

Steven

￥38,293

￥54,590 total

includes taxes & fees

Oct 27 - Oct 28

A beach with palm trees and lounge chairs.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

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

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

3. Chesapeake Beach Resort

Matecumbe

Suresh

￥22,321

￥33,966 total

includes taxes & fees

Oct 5 - Oct 6

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 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.

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

4. Amara Cay Resort

Matecumbe

MICHAEL

￥22,384

￥36,693 total

includes taxes & fees

Oct 18 - Oct 19

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.

5. La Jolla Resort

Matecumbe

Kayla

￥14,407

￥20,636 total

includes taxes & fees

Oct 1 - Oct 2

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

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

6. Hadley Resort and Marina

Matecumbe

weder

￥21,274

￥29,070 total

includes taxes & fees

Oct 1 - Oct 2

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 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.

7. The Islands of Islamorada

Matecumbe

Christian

￥74,298

￥93,749 total

includes taxes & fees

Oct 28 - Oct 29

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 beachside resort with a pool area, lounge chairs, and palm trees.

8. Pines & Palms Resort

Matecumbe

Colt

￥32,442

￥45,175 total

includes taxes & fees

Oct 15 - Oct 16

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 building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.

9. Breezy Palms Resort

Matecumbe

Zack

￥12,865

￥16,985 total

includes taxes & fees

Oct 1 - Oct 2

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

beata

￥49,585

￥67,293 total

includes taxes & fees

Oct 1 - Oct 2

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 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.

11. Sands of Islamorada

Matecumbe

Nicolas

￥30,223

￥36,126 total

includes taxes & fees

Oct 1 - Oct 2

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.

12. Casa Morada

Matecumbe

David

￥24,908

￥29,793 total

includes taxes & fees

Oct 7 - Oct 8

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.

A coastal resort with a beach, a swimming pool, and multiple buildings.

A resort with a pool, beach, and ocean view.

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

Islamorada

Eslita

￥33,874

￥49,619 total

includes taxes & fees

Oct 18 - Oct 19

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

A hotel room with a kitchenette, two beds, a desk, a television, and a ceiling fan.

A tropical garden with palm trees, various colorful plants, and a seating area with chairs.

A resort with a thatched-roof structure, palm trees, and lounge chairs on a sandy beach.

14. Hampton Inn Key Largo Manatee Bay

Key Largo

Cory

￥17,942

￥20,185 total

includes taxes & fees

Oct 7 - Oct 8

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

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

Key Largo

Omar Ahmad

￥16,146

￥23,154 total

includes taxes & fees

Oct 15 - Oct 16

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 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.

16. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

￥21,103

￥23,740 total

includes taxes & fees

Oct 8 - Oct 9

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.

17. Lime Tree Bay Resort

Long Key

Angela

￥18,187

￥27,544 total

includes taxes & fees

Oct 4 - Oct 5

A wooden deck with a view of the ocean and a palm tree.

A spacious dining area with high ceilings, wicker furniture, and large windows.

A coconut drink with a straw, a cherry, and a slice of fruit on a table by a pool with a waterfall and palm trees in the background.

A spacious interior with a high ceiling, large windows, and a central chandelier.

18. Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

Micheal

￥43,757

￥57,905 total

includes taxes & fees

Oct 12 - Oct 13

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.

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

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

19. Fisher Inn Resort & Marina

Islamorada

Alexandra

￥21,269

￥29,063 total

includes taxes & fees

Oct 13 - Oct 14

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

A wooden boardwalk leading to a building with a brick wall and a white roof.

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.

20. Drop Anchor

Islamorada

Payman

￥20,695

￥28,791 total

includes taxes & fees

Oct 6 - Oct 7

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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 weathered stone monument with a carved wave design, surrounded by palm trees and under 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

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

See all hotels in Upper Matecumbe Key

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

Top Upper Matecumbe Key Hotel Reviews

Lime Tree Bay Resort

10/10 Excellent

"Beautiful location, great amenities, and comfortable rooms"

Cheeca Lodge & Spa

10/10 Excellent

"All the place is amazing but the rooms needs a little be of work to upgrade, and the beach was not as we imagined"

Hadley Resort and Marina

10/10 Excellent

"First time staying and we enjoyed it"

Islander Resort

10/10 Excellent

"Amazing place would definitely recommend"

Amara Cay Resort

8/10 Good

"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"

Waterside Suites & Marina

10/10 Excellent

"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"

Casa Morada

10/10 Excellent

"always a favorite!"

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

￥14,424

￥16,227 total

Oct 1 - Oct 2

includes taxes & fees

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

￥14,584

￥16,407 total

Oct 1 - Oct 2

includes taxes & fees

9.2/10 Wonderful! (1,192 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

￥12,868

￥16,989 total

Oct 1 - Oct 2

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

￥17,942

￥20,185 total

Oct 7 - Oct 8

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

￥18,412

￥20,714 total

Oct 1 - Oct 2

includes taxes & fees

9.2/10 Wonderful! (1,011 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

￥22,520

￥25,335 total

Oct 28 - Oct 29

includes taxes & fees

7.8/10 Good! (1,021 reviews)

Hotels in Upper Matecumbe Key with star-rating

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Find hotels in Upper Matecumbe Key, FL from ￥16,227

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. Islander Resort

3. Chesapeake Beach Resort

4. Amara Cay Resort

5. La Jolla Resort

6. Hadley Resort and Marina

7. The Islands of Islamorada

8. Pines & Palms Resort

9. Breezy Palms Resort

10. Bayside Villas by Islander Resort

11. Sands of Islamorada

12. Casa Morada

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

14. Hampton Inn Key Largo Manatee Bay

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

16. Coconut Cove Resort and Marina

17. Lime Tree Bay Resort

18. Baker's Cay Resort Key Largo, Curio Collection by Hilton

19. Fisher Inn Resort & Marina

20. Drop Anchor

Stay near popular Upper Matecumbe Key attractions

Bud n' Mary's Dive Center

Florida Keys Brewing Co.

History of Diving Museum

Hurricane Monument

Islamorada Brewery & Distillery

MoradaWay Arts & Cultural District

Lorelei Restaurant & Cabana Bar

beach near Islamorada

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Lime Tree Bay Resort

Cheeca Lodge & Spa

Hadley Resort and Marina

Islander Resort

Amara Cay Resort

Waterside Suites & Marina

Casa Morada

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

Breezy Palms Resort

Hampton Inn Key Largo Manatee Bay

Sunset Cove Beach Resort

Creekside Inn

Hotels in Upper Matecumbe Key with star-rating

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