𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Upper Matecumbe Key from RM321 (2026) - 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 paved pathway leading to a beach with palm trees and a view of the ocean.

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

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

1. Islander Resort

Matecumbe

Steven

RM849

RM1,254 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

RM617

RM923 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 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.

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

3. Cheeca Lodge & Spa

Matecumbe

Kristin

RM812

RM1,212 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 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 beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

4. La Jolla Resort

Matecumbe

Brett

RM584

RM772 total

includes taxes & fees

22 Oct - 23 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.

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.

5. Amara Cay Resort

Matecumbe

Danielle

RM631

RM1,008 total

includes taxes & fees

18 Oct - 19 Oct

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

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

6. Hadley Resort and Marina

Matecumbe

weder

RM584

RM790 total

includes taxes & fees

9 Nov - 10 Nov

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.

7. Breezy Palms Resort

Matecumbe

Gavin

RM400

RM516 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

8. Pines & Palms Resort

Matecumbe

Colt

RM841

RM1,171 total

includes taxes & fees

21 Oct - 22 Oct

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

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.

A beach resort with palm trees, a thatched hut, and a purple building with a window.

9. La Siesta Resort & Villas

Matecumbe

Brianne

RM631

RM1,008 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

10. Sands of Islamorada

Matecumbe

Nicolas

RM780

RM932 total

includes taxes & fees

22 Oct - 23 Oct

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.

11. Bayside Villas by Islander Resort

Matecumbe

Brian

RM1,058

RM1,489 total

includes taxes & fees

27 Oct - 28 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 gated entrance to a resort with palm trees and a clear sky.

12. The Islands of Islamorada

Matecumbe

Christian

RM2,131

RM2,665 total

includes taxes & fees

18 Oct - 19 Oct

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.

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

13. Casa Morada

Matecumbe

RM639

RM765 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

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

Key Largo

Omar Ahmad

RM437

RM621 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 beachside resort with thatched-roof huts, palm trees, and a sandy area with rocks and wooden 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.

15. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

RM608

RM684 total

includes taxes & fees

27 Oct - 28 Oct

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.

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

16. Lime Tree Bay Resort

Long Key

Christopher Michael

RM506

RM752 total

includes taxes & fees

18 Oct - 19 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 wooden boardwalk leading to a building with a brick wall and a white roof.

17. Drop Anchor

Islamorada

Payman

RM455

RM655 total

includes taxes & fees

18 Oct - 19 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.

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

18. Fisher Inn Resort & Marina

Islamorada

Siobhan

RM584

RM791 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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

19. Atlantic Bay Resort

Tavernier

Annette

RM508

RM663 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

20. Hampton Inn Key Largo Manatee Bay

Key Largo

Samantha

RM466

RM524 total

includes taxes & fees

26 Oct - 27 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

Chesapeake Beach Resort

10/10 Excellent

"Great location"

Bayside Inn Key Largo

8/10 Good

"The lady at the desk TJ was kind and helpful. Very nice room and area"

Lime Tree Bay Resort

10/10 Excellent

"What to say really. We had a n absolute nightmare of a day on our way down to the hotel. We were due to land at Key West at 1200 but that turned into landing in Miami and then an 8 hour delay before finally touching down. The staff at the hotel were great contacting us throughout the day and being so friendly and attentive! We arrived finally at the hotel at 2230 and Robin at the check in was so fantastic staying back for us to be able to be checked in! We even got an upgrade. The only downside was due to the mess caused by flights, we were in the room for just a few hours. The resort was beautiful. The view from The balcony to the sea. The room was just so unbelievable it was like the stuff you get in dreams. Such a beautiful resort, beautiful room and I am certain we will be back! Thank you!"

Hawks Cay Resort

8/10 Good

"We love staying at Hawks Cay we have been going for years. The Property amenities are amazing. However, the Villa we stayed at (7039) was in horrible condition. Roaches in kitchen and bathroom, Shades on windows were broken in rooms. The jacuzzi outside was dirty and we were not able to use. We were extremely disappointed to have found it in that condition. I reported to the front office when we checked out. I didn't bother saying anything while there because I am pretty sure they didn't have another one available."

Hadley Resort and Marina

8/10 Good

"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."

Waterside Suites & Marina

10/10 Excellent

"Esther was really helpful. Very nice and professional. Room was spotless!! Balcony with a beautiful view."

La Jolla Resort

10/10 Excellent

"It was quaint and right on the water"

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."

The Caribbean Resort

10/10 Excellent

"Muy bien todo excelente servicio"

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

RM286

RM321 total

28 Oct - 29 Oct

includes taxes & fees

9.2/10 Wonderful! (1,191 reviews)

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

RM348

RM392 total

26 Oct - 27 Oct

includes taxes & fees

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

RM400

RM516 total

18 Oct - 19 Oct

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

RM466

RM524 total

26 Oct - 27 Oct

includes taxes & fees

8.8/10 Excellent! (1,106 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

RM478

RM537 total

20 Oct - 21 Oct

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

RM562

RM632 total

12 Nov - 13 Nov

includes taxes & fees

Upper Matecumbe Key hotels from RM321

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. La Jolla Resort

5. Amara Cay Resort

6. Hadley Resort and Marina

7. Breezy Palms Resort

8. Pines & Palms Resort

9. La Siesta Resort & Villas

10. Sands of Islamorada

11. Bayside Villas by Islander Resort

12. The Islands of Islamorada

13. Casa Morada

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

15. Coconut Cove Resort and Marina

16. Lime Tree Bay Resort

17. Drop Anchor

18. Fisher Inn Resort & Marina

19. Atlantic Bay Resort

20. Hampton Inn Key Largo Manatee Bay

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

Chesapeake Beach Resort

Bayside Inn Key Largo

Lime Tree Bay Resort

Hawks Cay Resort

Hadley Resort and Marina

Waterside Suites & Marina

La Jolla Resort

Pines & Palms Resort

The Caribbean Resort

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

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