Best Upper Matecumbe Key Hotels in 2026 from HK$809 - 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

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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

HK$1,169

HK$1,888 total

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

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

2. Chesapeake Beach Resort

Matecumbe

Suresh

HK$1,185

HK$1,774 total

includes taxes & fees

28 Sept - 29 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 bar area with a wooden counter, bar stools, and potted plants.

3. Islander Resort

Matecumbe

John

HK$1,835

HK$2,638 total

includes taxes & fees

28 Sept - 29 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.

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.

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

4. Amara Cay Resort

Matecumbe

MICHAEL

HK$1,212

HK$1,937 total

includes taxes & fees

28 Sept - 29 Sept

A beachside lounge with a wooden deck, thatched roof, and tropical 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.

5. Bayside Villas by Islander Resort

Matecumbe

beata

HK$1,933

HK$2,748 total

includes taxes & fees

28 Sept - 29 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.

6. Pines & Palms Resort

Matecumbe

Colt

HK$1,546

HK$2,171 total

includes taxes & fees

1 Oct - 2 Oct

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 beach with wooden lounge chairs, palm trees, and a clear 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.

7. La Jolla Resort

Matecumbe

Kayla

HK$759

HK$1,074 total

includes taxes & fees

28 Sept - 29 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.

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.

8. Hadley Resort and Marina

Matecumbe

weder

HK$927

HK$1,298 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

A pool area with clear blue water, white lounge chairs, and palm trees.

9. The Islands of Islamorada

Matecumbe

Christian

HK$3,640

HK$4,600 total

includes taxes & fees

25 Oct - 26 Oct

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

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

10. Breezy Palms Resort

Matecumbe

Debra

HK$641

HK$847 total

includes taxes & fees

29 Sept - 30 Sept

A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

A spacious living area with a round dining table, a sofa, and a TV mounted on the wall.

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.

11. Sands of Islamorada

Matecumbe

Nicolas

HK$1,506

HK$1,800 total

includes taxes & fees

1 Oct - 2 Oct

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.

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

12. Casa Morada

Matecumbe

David

HK$1,228

HK$1,470 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.

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

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

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

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

Islamorada

Eslita

HK$1,625

HK$2,402 total

includes taxes & fees

6 Oct - 7 Oct

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.

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

14. Fisher Inn Resort & Marina

Islamorada

Alexandra

HK$993

HK$1,373 total

includes taxes & fees

30 Sept - 1 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 wooden boardwalk leading to a building with a brick wall and a white roof.

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

15. Drop Anchor

Islamorada

Payman

HK$1,031

HK$1,435 total

includes taxes & fees

28 Sept - 29 Sept

A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

A hallway with a tiled floor, a painting on the wall, a lamp, and a view of a pool area.

A wooden sign with the name 'Creekside' above a white pergola entrance.

A waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

16. Creekside Inn

Tavernier

Terry

HK$1,122

HK$1,263 total

includes taxes & fees

27 Sept - 28 Sept

A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

A sign for Matecumbe Resort with a full kitchen and heated pool.

A beach view with palm trees and a thatched-roof structure.

A compact kitchen with modern appliances, a dining area with a sofa, and a large window providing natural light.

17. Matecumbe Resort

Matecumbe

Adrian

HK$1,009

HK$1,136 total

includes taxes & fees

27 Sept - 28 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden chairs.

18. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

HK$1,169

HK$1,315 total

includes taxes & fees

27 Sept - 28 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 hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, framed artwork on the wall, and an air conditioning unit.

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

A bedroom with a bed, a nightstand, a chair, and a door.

19. The Ocean View Inn & Pub

Islamorada

Maria

HK$1,461

HK$1,644 total

includes taxes & fees

27 Sept - 28 Sept

Two Adirondack chairs on a sandy beach with a wooden pier extending into calm water.

A bathroom with a white vanity, a mirror, a sink, a cabinet, and a towel rack.

A hotel room with a bed, a sofa, a chair, a nightstand, a lamp, and a window.

20. Coconut Palm Inn

Tavernier

HK$1,475

HK$1,968 total

includes taxes & fees

27 Sept - 28 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.

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Learn more about Upper Matecumbe Key

Venture to sights like Bud n' Mary's Dive Center and Lorelei Restaurant & Cabana Bar as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key

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

Top Upper Matecumbe Key Hotel Reviews

The Pelican Key Largo Cottages

8/10 Good

"Was clean a little sparse & in need of updating. The staff was extremely helpful. The private beach was very nice."

Islander Resort

8/10 Good

"I liked the fact that our rear outside seating area was quite private because of the trees and bushes growing around the property. Very peaceful and also just a couple of minutes walk from the sea."

Waterside Suites & Marina

8/10 Good

"Comfortable bed, clean . It’s off the busy road and close to restaurants"

Chesapeake Beach Resort

8/10 Good

"I liked the breakfast. One pool was being worked on and the pool workers helped themselves to the free breakfast. Some of them stood in the coffee and drink area and ate their free breakfast. The tree trimmers took up some of relaxing areas and they were noisy. The cleaning staff and the front desk staff were very good. The breakfast cook was friendly. The spa was hot but no jet action. We probably won’t be coming back. Thanks"

Casa Morada

10/10 Excellent

"always a favorite!"

Lime Tree Bay Resort

10/10 Excellent

"Very lovely stay, everyone who worked there was super friendly!"

La Jolla Resort

8/10 Good

"Loved the amenities"

Hawks Cay Resort

10/10 Excellent

"The resort was beautiful. The food was good but pricey. We loved having the option to have the food/drinks delivered by the pool. The bed was comfortable and the Cabana room was very convenient to have right next to the adult pool area. Our only issue was the AC fluctuated a bit and a few nights it got too cold (one of our neighbors room was way too warm so it could have been worse). And the hot water wasn't really hot enough to take a decent shower. But overall we felt these were minor issues and the staff was so amazing we felt well taken care of otherwise."

Bayside Inn Key Largo

10/10 Excellent

"Great location !!"

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

HK$719

HK$809 total

27 Sept - 28 Sept

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

HK$727

HK$817 total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,188 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

HK$641

HK$847 total

29 Sept - 30 Sept

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

HK$918

HK$1,033 total

1 Oct - 2 Oct

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

HK$932

HK$1,049 total

6 Oct - 7 Oct

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

HK$1,122

HK$1,263 total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (1,020 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$809

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. Cheeca Lodge & Spa

2. Chesapeake Beach Resort

3. Islander Resort

4. Amara Cay Resort

5. Bayside Villas by Islander Resort

6. Pines & Palms Resort

7. La Jolla Resort

8. Hadley Resort and Marina

9. The Islands of Islamorada

10. Breezy Palms Resort

11. Sands of Islamorada

12. Casa Morada

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

14. Fisher Inn Resort & Marina

15. Drop Anchor

16. Creekside Inn

17. Matecumbe Resort

18. Coconut Cove Resort and Marina

19. The Ocean View Inn & Pub

20. Coconut Palm Inn

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

The Pelican Key Largo Cottages

Islander Resort

Waterside Suites & Marina

Chesapeake Beach Resort

Casa Morada

Lime Tree Bay Resort

La Jolla Resort

Hawks Cay Resort

Bayside Inn Key Largo

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

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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