Top 10 Hotels in Upper Matecumbe Key, FL from ₩142,378 - 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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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

₩203,422

₩328,691 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

2. Islander Resort

Matecumbe

John

₩289,365

₩425,363 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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.

3. Hadley Resort and Marina

Matecumbe

weder

₩161,304

₩226,017 total

includes taxes & fees

Sep 28 - Sep 29

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.

4. La Jolla Resort

Matecumbe

Leslie

₩132,088

₩187,004 total

includes taxes & fees

Sep 28 - Sep 29

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

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

5. Chesapeake Beach Resort

Matecumbe

Suresh

₩206,221

₩308,795 total

includes taxes & fees

Sep 28 - Sep 29

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

6. Bayside Villas by Islander Resort

Matecumbe

beata

₩336,535

₩470,755 total

includes taxes & fees

Sep 29 - Sep 30

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

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.

7. Amara Cay Resort

Matecumbe

MICHAEL

₩211,034

₩337,254 total

includes taxes & fees

Sep 27 - Sep 28

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

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

8. Pines & Palms Resort

Matecumbe

Colt

₩269,091

₩377,994 total

includes taxes & fees

Oct 1 - Oct 2

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

Debra

₩111,609

₩147,352 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 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.

10. Sands of Islamorada

Matecumbe

Nicolas

₩262,128

₩313,325 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 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.

11. The Islands of Islamorada

Matecumbe

Christian

₩552,927

₩708,361 total

includes taxes & fees

Oct 1 - Oct 2

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

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

12. Casa Morada

Matecumbe

David

₩213,798

₩255,889 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

13. Fisher Inn Resort & Marina

Islamorada

Alexandra

₩172,909

₩239,070 total

includes taxes & fees

Sep 28 - Sep 29

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

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

A wooden interior with a large window overlooking a beach with a thatched umbrella and lounge chairs.

14. Rock Reef Resort

Rock Harbor

Tia

₩126,557

₩142,378 total

includes taxes & fees

Sep 27 - Sep 28

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

A tree with string lights, a wooden bench, and a building in the background.

A beach with lounge chairs, kayaks, and a wooden pier.

A modern living room with a dark brown sofa, a coffee table, and a blue lamp. There is a kitchen area with a microwave and a coffee machine. A painting of a beach scene is on the wall.

15. Drift Hotel

Key Largo

kelly

₩127,992

₩159,350 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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.

16. Creekside Inn

Tavernier

Terry

₩195,367

₩219,805 total

includes taxes & fees

Oct 4 - Oct 5

A multi-story hotel with balconies, palm trees, and a view of the water.

A spacious lobby with a reception desk, seating area, and a large aquarium display.

A beachside area with palm trees, a wooden bench, and a wheelchair-accessible sign.

A swimming pool with lounge chairs and palm trees.

17. Marina Del Mar Resort and Marina

Key Largo

Francisco

₩189,770

₩251,895 total

includes taxes & fees

Sep 26 - Sep 27

A bedroom with a large bed, a ceiling fan, a TV on the wall, and a view of the beach through a window.

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

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

18. Lime Tree Bay Resort

Long Key

milayda

₩157,744

₩238,898 total

includes taxes & fees

Sep 28 - Sep 29

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.

A garden with various trees and a gravel path.

A balcony with a view of the sea, a beach, and a thatched hut.

19. Sunset Cove Beach Resort

Key Largo

Payton

₩159,818

₩179,802 total

includes taxes & fees

Oct 1 - Oct 2

A balcony with a view of the sea, a table, and two chairs.

A bedroom with a bed, a TV mounted on the wall, a window with blinds, and a chandelier.

A swimming pool with lounge chairs and umbrellas, a fenced area, and a building with a door.

A marina with boats docked along a waterfront, surrounded by buildings and palm trees.

20. Waterside Suites & Marina

Key Largo

Thuc

₩167,311

₩226,622 total

includes taxes & fees

Sep 29 - Sep 30

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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 exploring the galleries in Keys History & Discovery Center 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 Lorelei Restaurant & Cabana Bar.

See all hotels in Upper Matecumbe Key

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

Top Upper Matecumbe Key Hotel Reviews

Amara Cay Resort

10/10 Excellent

"We stayed with a large group of people. Everything about our stay was amazing. The amenities are well kept, grounds are beautiful. The hotel is clean and the staff are friendly."

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."

Chesapeake Beach Resort

8/10 Good

"Very nice property even though they have some remodeling going on, the place is agreeable. The staff in general was amazing, at least my experience was great. I visited the place few days after an accident with some limitations and my mother, an elderly person, they went an extra step to assist us and make our stay memorable at all times. My villa was spacious, clean and well located."

Bayside Inn Key Largo

10/10 Excellent

"Great location !!"

The Pelican Key Largo Cottages

10/10 Excellent

"The place had character and culture that modern sterile resorts do not."

Casa Morada

10/10 Excellent

"Very helpful staff and great location"

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

₩126,557

₩142,378 total

Sep 27 - Sep 28

includes taxes & fees

9.2/10 Wonderful! (1,188 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

₩111,609

₩147,352 total

Oct 1 - Oct 2

includes taxes & fees

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

₩132,931

₩149,547 total

Oct 5 - Oct 6

includes taxes & fees

9/10 Wonderful! (1,004 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

₩158,028

₩177,782 total

Oct 6 - Oct 7

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

₩159,818

₩179,802 total

Oct 1 - Oct 2

includes taxes & fees

9.2/10 Wonderful! (1,009 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

₩195,367

₩219,805 total

Oct 4 - Oct 5

includes taxes & fees

Hotels in Upper Matecumbe Key with star-rating

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from ₩142,378

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. Islander Resort

3. Hadley Resort and Marina

4. La Jolla Resort

5. Chesapeake Beach Resort

6. Bayside Villas by Islander Resort

7. Amara Cay Resort

8. Pines & Palms Resort

9. Breezy Palms Resort

10. Sands of Islamorada

11. The Islands of Islamorada

12. Casa Morada

13. Fisher Inn Resort & Marina

14. Rock Reef Resort

15. Drift Hotel

16. Creekside Inn

17. Marina Del Mar Resort and Marina

18. Lime Tree Bay Resort

19. Sunset Cove Beach Resort

20. Waterside Suites & Marina

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

Amara Cay Resort

Hawks Cay Resort

Chesapeake Beach Resort

Bayside Inn Key Largo

The Pelican Key Largo Cottages

Casa Morada

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

Breezy Palms Resort

The Pelican Key Largo Cottages

Hampton Inn Key Largo Manatee Bay

Sunset Cove Beach Resort

Creekside Inn

Hotels in Upper Matecumbe Key with star-rating

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