Best Upper Matecumbe Key Hotels in 2026 from HK$674 - 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 bar area with a wooden counter, bar stools, and potted plants.

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

1. Islander Resort

Matecumbe

Bryan

HK$1,532

HK$2,297 total

includes taxes & fees

15 Nov - 16 Nov

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.

2. Chesapeake Beach Resort

Matecumbe

Dianne

HK$1,185

HK$1,775 total

includes taxes & fees

20 Oct - 21 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 spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

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

3. Cheeca Lodge & Spa

Matecumbe

James

HK$1,562

HK$2,331 total

includes taxes & fees

20 Oct - 21 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

Ronald

HK$1,213

HK$1,939 total

includes taxes & fees

21 Oct - 22 Oct

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

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

5. La Jolla Resort

Matecumbe

Brett

HK$1,123

HK$1,484 total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

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

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 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.

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

7. Pines & Palms Resort

Matecumbe

Michael

HK$1,406

HK$2,014 total

includes taxes & fees

20 Oct - 21 Oct

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

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

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.

8. La Siesta Resort & Villas

Matecumbe

Brianne

HK$1,213

HK$1,939 total

includes taxes & fees

15 Nov - 16 Nov

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

9. Breezy Palms Resort

Matecumbe

Gavin

HK$770

HK$991 total

includes taxes & fees

21 Oct - 22 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.

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

10. Bayside Villas by Islander Resort

Matecumbe

Brian

HK$1,808

HK$2,608 total

includes taxes & fees

25 Oct - 26 Oct

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.

11. The Islands of Islamorada

Matecumbe

Christian

HK$4,097

HK$5,123 total

includes taxes & fees

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

A compact, well-lit room with a bed, bedside table, and a small seating area.

12. Sands of Islamorada

Matecumbe

Nicolas

HK$1,499

HK$1,792 total

includes taxes & fees

22 Oct - 23 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

26 Oct - 27 Oct

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

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

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

A clear blue pool with lounge chairs and palm trees.

14. Hampton Inn Key Largo Manatee Bay

Key Largo

Mee

HK$937

HK$1,054 total

includes taxes & fees

25 Oct - 26 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 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.

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

Key Largo

Omar Ahmad

HK$841

HK$1,194 total

includes taxes & fees

26 Oct - 27 Oct

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

A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.

16. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

HK$1,169

HK$1,316 total

includes taxes & fees

26 Oct - 27 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.

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.

17. Fisher Inn Resort & Marina

Islamorada

Robyn

HK$1,248

HK$1,660 total

includes taxes & fees

20 Oct - 21 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 bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

18. Lime Tree Bay Resort

Long Key

Christopher Michael

HK$972

HK$1,447 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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

19. Drop Anchor

Islamorada

Payman

HK$979

HK$1,376 total

includes taxes & fees

20 Oct - 21 Oct

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

A spacious bedroom with a bed, a dresser, a television, and a view of the sea through the window.

A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

A compact living space with a balcony, a television, and a dining area.

20. Atlantic Bay Resort

Tavernier

Annette

HK$1,070

HK$1,381 total

includes taxes & fees

27 Oct - 28 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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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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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

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

10/10 Excellent

"clean room and very unique location. The breakfast was just ok and overpriced"

La Jolla Resort

10/10 Excellent

"It looks a little rough when you drive in but wow - once you are at the resort it is homey and clean and nice. The staff is super helpful. The office has cold drinks, ice, snacks, beach towels, snorkel gear, life vests, fishing gear (and bait), paddles, and other things to make the stay enjoyable. Off the back there is swim access, lounge chairs, hammocks, bocce ball. I’m probably forgetting other things. The rooms are spacious and well equipped for a short or longer term stay. Highly recommend."

Amara Cay Resort

8/10 Good

"Clean room and nice amenities. Parking was good. Common areas very well designed."

Waterside Suites & Marina

8/10 Good

"Only issues we had that was no big deal was the room slept 4 people amd there was only 1 towel and 1 wash cloth. Once we asked the staff for more the stay was great room was clean and modern and property was presented very well and clean! I would definitely stay here again"

Chesapeake Beach Resort

10/10 Excellent

"Very professional reception, room clean staff very polite"

Hawks Cay Resort

8/10 Good

"Our villa was right next to the workers building. Not an ideal spot for a “premium” villa. Also when they were cutting lawn and blowing leaves they were blowing everything all over our rental cars. Parking was tough because I think employees were also parking in guest spots. Again I think this was due to the location of our villa. We were never told what to do with our garbage or if housekeeping would come clean. Found out later you need to specifically request it 24 hrs in advance. It was off season so nice and quite not too many people so they definitely could have put us elsewhere. Other than that we really enjoyed ourselves and plan to go back next time we would just be specific on check in about the location they put us in."

Lime Tree Bay Resort

10/10 Excellent

"Excelente lugar , tranquilo , limpio y maravilloso para ver un atardecer"

Islander Resort

10/10 Excellent

"We had an incredible stay here. Great views, delicious food, and the staff went above and beyond to make our stay exceptional. We already can’t wait to come back!"

Bayside Inn Key Largo

10/10 Excellent

"The room was very clean and comfortable. Best shower ever! Nice shampoo, conditioner, and body lotion. Great fluffy towels, and ice cold air conditioning… What more could you want? Great location next to snooks restaurant/bar. Refreshing little pool next to a beach if you wanna sit in the sand. Cute chickens, roosters, and iguanas roaming around. Walking distance to Burger King, Starbucks, sandal, factory, Walgreens… Just a great hotel and a great location!"

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

HK$599

HK$674 total

27 Oct - 28 Oct

includes taxes & fees

9.2/10 Wonderful! (1,194 reviews)

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

HK$728

HK$819 total

26 Oct - 27 Oct

includes taxes & fees

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

HK$770

HK$991 total

21 Oct - 22 Oct

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

HK$918

HK$1,033 total

20 Oct - 21 Oct

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

HK$937

HK$1,054 total

25 Oct - 26 Oct

includes taxes & fees

8.8/10 Excellent! (1,111 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

HK$1,080

HK$1,215 total

12 Nov - 13 Nov

includes taxes & fees

7.8/10 Good! (1,025 reviews)

Hotels in Upper Matecumbe Key with star-rating

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Things to do in Duck Key

Upper Matecumbe Key hotels from HK$674

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. La Siesta Resort & Villas

9. Breezy Palms Resort

10. Bayside Villas by Islander Resort

11. The Islands of Islamorada

12. Sands of Islamorada

13. Casa Morada

14. Hampton Inn Key Largo Manatee Bay

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

16. Coconut Cove Resort and Marina

17. Fisher Inn Resort & Marina

18. Lime Tree Bay Resort

19. Drop Anchor

20. Atlantic Bay Resort

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

Lorelei Restaurant & Cabana Bar

MoradaWay Arts & Cultural District

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

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

La Jolla Resort

Amara Cay Resort

Waterside Suites & Marina

Chesapeake Beach Resort

Hawks Cay Resort

Lime Tree Bay Resort

Islander Resort

Bayside Inn Key Largo

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

The Pelican Key Largo Cottages

Breezy Palms Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Hotels in Upper Matecumbe Key with star-rating

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