Best Upper Matecumbe Key Hotels in 2026 from HK$618 - 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

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

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

A paved pathway leading to a beach with palm trees and a view of the ocean.

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

1. Islander Resort

Matecumbe

Steven

HK$1,632

HK$2,410 total

includes taxes & fees

18 Oct - 19 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 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

Phelicia

HK$1,185

HK$1,775 total

includes taxes & fees

18 Oct - 19 Oct

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 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.

3. Cheeca Lodge & Spa

Matecumbe

Morgan

HK$1,562

HK$2,331 total

includes taxes & fees

19 Oct - 20 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.

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

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

A resort pool with palm trees, beach chairs, and umbrellas.

4. Amara Cay Resort

Matecumbe

Danielle

HK$1,213

HK$1,939 total

includes taxes & fees

18 Oct - 19 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.

5. La Jolla Resort

Matecumbe

Brett

HK$1,011

HK$1,359 total

includes taxes & fees

15 Oct - 16 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.

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.

6. Hadley Resort and Marina

Matecumbe

weder

HK$1,123

HK$1,520 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

A coastal resort with a marina, clear blue water, and lush greenery.

7. Pines & Palms Resort

Matecumbe

Colt

HK$1,617

HK$2,252 total

includes taxes & fees

15 Oct - 16 Oct

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

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

A beach with thatched umbrellas, palm trees, and lounge chairs.

8. Breezy Palms Resort

Matecumbe

Gavin

HK$770

HK$991 total

includes taxes & fees

18 Oct - 19 Oct

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 row of colorful beach huts with palm trees in the background.

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

9. La Siesta Resort & Villas

Matecumbe

Brianne

HK$1,319

HK$2,058 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

10. The Islands of Islamorada

Matecumbe

Christian

HK$4,096

HK$5,123 total

includes taxes & fees

19 Oct - 20 Oct

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.

11. Bayside Villas by Islander Resort

Matecumbe

Brian

HK$2,034

HK$2,862 total

includes taxes & fees

21 Oct - 22 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 two-story building with a balcony, surrounded by palm trees and a sandy ground.

12. Sands of Islamorada

Matecumbe

Nicolas

HK$1,483

HK$1,775 total

includes taxes & fees

19 Oct - 20 Oct

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.

13. Casa Morada

Matecumbe

David

HK$1,229

HK$1,471 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Islamorada

Liosbel

HK$1,877

HK$2,686 total

includes taxes & fees

3 Nov - 4 Nov

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.

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

Key Largo

Omar Ahmad

HK$840

HK$1,194 total

includes taxes & fees

15 Oct - 16 Oct

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

A clear blue pool with lounge chairs and palm trees.

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.

16. Hampton Inn Key Largo Manatee Bay

Key Largo

Samantha

HK$907

HK$1,020 total

includes taxes & fees

20 Oct - 21 Oct

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.

17. Fisher Inn Resort & Marina

Islamorada

Siobhan

HK$1,264

HK$1,678 total

includes taxes & fees

8 Nov - 9 Nov

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 resort with thatched-roof structures, palm trees, and a sandy beach area.

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

18. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

HK$1,169

HK$1,315 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

19. Lime Tree Bay Resort

Long Key

Katie

HK$907

HK$1,373 total

includes taxes & fees

15 Oct - 16 Oct

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.

20. Drop Anchor

Islamorada

Payman

HK$874

HK$1,258 total

includes taxes & fees

18 Oct - 19 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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A stone monument with a relief sculpture, surrounded by palm trees and 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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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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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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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 shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top Upper Matecumbe Key Hotel Reviews

Amara Cay Resort

10/10 Excellent

"Beautiful"

Breezy Palms Resort

8/10 Good

"The property was clean and extremely well lit. The parking was great. The room had a full kitchen which was a huge plus. The layout of the room and the furnishings were beautiful and up to date. The room was spacious and comfortable. The staff were friendly and hospitable. I didnt pay much attention when booking but free kayaks or bikes would have been a great additional amenity. I thought it was extra convenient to have boats for rent on property. This was also an added benefit. I will definitely stay here again in the future."

Bayside Inn Key Largo

10/10 Excellent

"Fabulous resort, great arrangement with Snook bar next door. The bantams were intriguing. Room good, but, dirty pair of underpants left in a draw by a previous guest."

La Jolla Resort

10/10 Excellent

"It was quaint and right on the water"

Lime Tree Bay Resort

10/10 Excellent

"We will definitely stay here again! Beautiful property that was always clean and peaceful."

Waterside Suites & Marina

10/10 Excellent

"Easy checkin. Good pool. Balconies overlook an inlet with docked boats. Saw a lot of fish swimming, as well as divers taking lessons."

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

10/10 Excellent

"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"

Pines & Palms Resort

10/10 Excellent

"This was an absolute dream vacation for my husband and I. The amenities were fantastic and the property was immaculate. The staff were exceedingly concerned about our comfort and asking if we needed anything. The location couldn’t have been better. We will be back."

Hadley Resort and Marina

10/10 Excellent

"Great place for the money!"

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

HK$549

HK$618 total

28 Oct - 29 Oct

includes taxes & fees

9.2/10 Wonderful! (1,186 reviews)

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

HK$764

HK$860 total

26 Oct - 27 Oct

includes taxes & fees

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

HK$770

HK$991 total

18 Oct - 19 Oct

includes taxes & fees

9/10 Wonderful! (768 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

HK$907

HK$1,020 total

20 Oct - 21 Oct

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

HK$918

HK$1,033 total

21 Oct - 22 Oct

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

HK$1,080

HK$1,215 total

12 Nov - 13 Nov

includes taxes & fees

Hotels in Upper Matecumbe Key with star-rating

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Things to do in Duck Key

Upper Matecumbe Key hotels from HK$618

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upper Matecumbe Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Upper Matecumbe Key hotels

1. Islander Resort

2. Chesapeake Beach Resort

3. Cheeca Lodge & Spa

4. Amara Cay Resort

5. La Jolla Resort

6. Hadley Resort and Marina

7. Pines & Palms Resort

8. Breezy Palms Resort

9. La Siesta Resort & Villas

10. The Islands of Islamorada

11. Bayside Villas by Islander Resort

12. Sands of Islamorada

13. Casa Morada

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

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

16. Hampton Inn Key Largo Manatee Bay

17. Fisher Inn Resort & Marina

18. Coconut Cove Resort and Marina

19. Lime Tree Bay Resort

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

beach near Islamorada

MoradaWay Arts & Cultural District

Lorelei Restaurant & Cabana Bar

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Amara Cay Resort

Breezy Palms Resort

Bayside Inn Key Largo

La Jolla Resort

Lime Tree Bay Resort

Waterside Suites & Marina

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

Pines & Palms Resort

Hadley Resort and Marina

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

The Pelican Key Largo Cottages

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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