Upper Matecumbe Key Hotel & Accommodation Deals 2026 from AU$124 - Compare prices by date

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 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.

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

1. Islander Resort

Matecumbe

Bryan

AU$421

includes taxes & fees

15 Nov - 16 Nov

A beach with palm trees and lounge chairs.

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.

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

2. Chesapeake Beach Resort

Matecumbe

Dianne

AU$306

includes taxes & fees

26 Oct - 27 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 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.

3. La Jolla Resort

Matecumbe

Brett

AU$272

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.

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

4. Amara Cay Resort

Matecumbe

Ronald

AU$348

includes taxes & fees

21 Oct - 22 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 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.

5. Cheeca Lodge & Spa

Matecumbe

James

AU$379

includes taxes & fees

21 Oct - 22 Oct

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

6. Breezy Palms Resort

Matecumbe

Gavin

AU$224

includes taxes & fees

2 Nov - 3 Nov

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.

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

7. Hadley Resort and Marina

Matecumbe

weder

AU$279

includes taxes & fees

9 Nov - 10 Nov

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 beach with colorful buildings, kayaks, and lounge chairs.

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

8. La Siesta Resort & Villas

Matecumbe

Brianne

AU$356

includes taxes & fees

15 Nov - 16 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 coastal resort with a marina, clear blue water, and lush greenery.

9. Pines & Palms Resort

Matecumbe

Michael

AU$389

includes taxes & fees

1 Nov - 2 Nov

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.

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

10. Bayside Villas by Islander Resort

Matecumbe

Brian

AU$457

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

11. Sands of Islamorada

Matecumbe

Nicolas

AU$329

includes taxes & fees

22 Oct - 23 Oct

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

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

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

A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

12. The Islands of Islamorada

Matecumbe

Christian

AU$871

includes taxes & fees

29 Oct - 30 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.

13. Casa Morada

Matecumbe

David

AU$270

includes taxes & fees

26 Oct - 27 Oct

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 spacious living area with a large island, wooden furniture, and a ceiling fan.

14. Lime Tree Bay Resort

Long Key

Christopher Michael

AU$265

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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

AU$179

includes taxes & fees

21 Oct - 22 Oct

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

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

A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

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

16. Rock Reef Resort

Rock Harbor

Jared

AU$124

includes taxes & fees

27 Oct - 28 Oct

A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

A pathway lined with palm trees and a speed limit sign of 5 MPH.

A bakery display case with various muffins and frittatas labeled with flavors like blueberry, cranberry orange, banana walnut, chocolate, egg cheese vegetable fritta, egg sausage fritta, and egg cheese fritta.

17. Seafarer Key Largo

Rock Harbor

Soraya

AU$204

includes taxes & fees

20 Oct - 21 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 resort with a pool, multiple buildings, and a waterfront view.

A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.

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

Key Largo

Omar Ahmad

AU$219

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 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.

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

19. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

AU$241

includes taxes & fees

26 Oct - 27 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.

20. Atlantic Bay Resort

Tavernier

Annette

AU$253

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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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

Recent Reviews in Upper Matecumbe Key

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 accommodation in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

AU$124

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

AU$150

26 Oct - 27 Oct

includes taxes & fees

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

AU$169

4 Nov - 5 Nov

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

AU$193

25 Oct - 26 Oct

includes taxes & fees

8.8/10 Excellent! (1,111 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

AU$216

18 Nov - 19 Nov

includes taxes & fees

7.8/10 Good! (1,025 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

AU$224

2 Nov - 3 Nov

includes taxes & fees

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Car hire near Kendall

Book Hotels in Upper Matecumbe Key on Expedia.com

Search Upper Matecumbe Key hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upper Matecumbe Key

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Upper Matecumbe Key hotels

1. Islander Resort

2. Chesapeake Beach Resort

3. La Jolla Resort

4. Amara Cay Resort

5. Cheeca Lodge & Spa

6. Breezy Palms Resort

7. Hadley Resort and Marina

8. La Siesta Resort & Villas

9. Pines & Palms Resort

10. Bayside Villas by Islander Resort

11. Sands of Islamorada

12. The Islands of Islamorada

13. Casa Morada

14. Lime Tree Bay Resort

15. Drift Hotel

16. Rock Reef Resort

17. Seafarer Key Largo

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

19. Coconut Cove Resort and Marina

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

MoradaWay Arts & Cultural District

Lorelei Restaurant & Cabana Bar

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Recent Reviews in Upper Matecumbe Key

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 accommodation in Upper Matecumbe Key

Rock Reef Resort

The Pelican Key Largo Cottages

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Breezy Palms Resort

Explore a world of travel with Expedia

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