Upper Matecumbe Key Holiday Rentals, Islamorada: Private House Rentals

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

A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Matecumbe

Jessica

฿4,934

฿7,972 total

includes taxes & fees

7 Sept - 8 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 swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

2. Chesapeake Beach Resort

Matecumbe

Yeniaris

฿4,965

฿7,435 total

includes taxes & fees

8 Sept - 9 Sept

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

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

3. Islander Resort

Matecumbe

Sonia

฿8,079

฿11,324 total

includes taxes & fees

22 Sept - 23 Sept

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 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

adrian

฿3,417

฿4,776 total

includes taxes & fees

31 Aug - 1 Sept

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 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.

5. Hadley Resort and Marina

Matecumbe

RAIBEL

฿3,844

฿5,405 total

includes taxes & fees

20 Sept - 21 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 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 resort pool with palm trees, beach chairs, and umbrellas.

6. Amara Cay Resort

Matecumbe

David A

฿4,895

฿7,928 total

includes taxes & fees

1 Sept - 2 Sept

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.

7. Bayside Villas by Islander Resort

Matecumbe

beata

฿7,510

฿10,683 total

includes taxes & fees

7 Sept - 8 Sept

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 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.

8. La Siesta Resort & Villas

Matecumbe

Brianne

฿4,448

฿7,425 total

includes taxes & fees

1 Sept - 2 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 beachside resort with a pool area, lounge chairs, and palm trees.

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

A coastal resort with a marina, clear blue water, and lush greenery.

9. Pines & Palms Resort

Matecumbe

Isabel

฿4,949

฿7,393 total

includes taxes & fees

31 Aug - 1 Sept

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 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.

10. Breezy Palms Resort

Matecumbe

Orlando

฿3,307

฿4,248 total

includes taxes & fees

1 Sept - 2 Sept

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

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.

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

11. The Islands of Islamorada

Matecumbe

Christian

฿11,920

฿15,474 total

includes taxes & fees

30 Aug - 31 Aug

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 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.

12. Sands of Islamorada

Matecumbe

Virginia

฿6,357

฿7,599 total

includes taxes & fees

31 Aug - 1 Sept

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

Lois

฿5,483

฿6,541 total

includes taxes & fees

31 Aug - 1 Sept

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

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

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.

14. Fisher Inn Resort & Marina

Islamorada

MARC

฿3,844

฿5,405 total

includes taxes & fees

21 Sept - 22 Sept

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.

An outdoor dining area with round tables and chairs, a thatched roof, and a view of the sea.

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

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

Islamorada

Ana

฿5,801

฿8,948 total

includes taxes & fees

7 Sept - 8 Sept

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.

16. Drop Anchor

Islamorada

Marianela

฿3,722

฿5,346 total

includes taxes & fees

30 Aug - 31 Aug

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

A beach with palm trees, a thatched-roof hut, and lounge chairs.

17. Coconut Cove Resort and Marina

Islamorada

Lisa C

฿4,934

฿5,550 total

includes taxes & fees

30 Aug - 31 Aug

A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

A swimming pool with a 5 ft depth marker, surrounded by palm trees and a white picket fence.

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.

18. The Ocean View Inn & Pub

Islamorada

Patrice

฿6,169

฿6,939 total

includes taxes & fees

31 Aug - 1 Sept

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

A compact kitchen with wooden cabinets, a refrigerator, and a window with curtains.

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.

19. Matecumbe Resort

Matecumbe

paul

฿4,440

฿4,995 total

includes taxes & fees

30 Aug - 31 Aug

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

A boat with a covered deck, metal railings, and a table with chairs.

A row of floating cottages with balconies and outdoor seating, docked along a waterway.

A kitchen with white cabinets, a microwave, a stove, and a refrigerator.

20. Treasure Harbor

Islamorada

Molly

฿4,142

฿9,316 total

includes taxes & fees

30 Aug - 31 Aug

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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 family-friendly 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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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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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

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

10/10 Excellent

"Nice property with great dining options and activities for the whole family."

Bayside Inn Key Largo

10/10 Excellent

"Great place! Close to everything in Key Largo. Staff was great. We will need to get a bigger room next time we visit. We will be back."

Islander Resort

10/10 Excellent

"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"

Waterside Suites & Marina

10/10 Excellent

"Me encantó la verdad. Fuimos un grupo familiar todos. Pero el echo de la cocina. El barbecue abajo. La piscina calentica. La verdad a nosotros nos encantó."

Casa Morada

8/10 Good

"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"The property was situated to make you feel like you were in a tropical paradise tucked away from the rest of the key. Very clean and nice. The staff was amazing and the private beach was one of the best."

The Caribbean Resort

10/10 Excellent

"Excellent place to stay!"

Pines & Palms Resort

8/10 Good

"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

฿3,034

฿3,414 total

1 Sept - 2 Sept

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

฿3,307

฿4,248 total

1 Sept - 2 Sept

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

฿4,112

฿4,626 total

8 Sept - 9 Sept

includes taxes & fees

Drift Hotel

95320 Overseas Hwy Key Largo FL

฿3,852

฿4,706 total

14 Sept - 15 Sept

includes taxes & fees

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

฿4,286

฿4,822 total

7 Sept - 8 Sept

includes taxes & fees

8.8/10 Excellent! (1,071 reviews)

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

฿4,602

฿6,109 total

30 Aug - 31 Aug

includes taxes & fees

8.6/10 Excellent! (1,873 reviews)

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from ฿2,603

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. La Jolla Resort

5. Hadley Resort and Marina

6. Amara Cay Resort

7. Bayside Villas by Islander Resort

8. La Siesta Resort & Villas

9. Pines & Palms Resort

10. Breezy Palms Resort

11. The Islands of Islamorada

12. Sands of Islamorada

13. Casa Morada

14. Fisher Inn Resort & Marina

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

16. Drop Anchor

17. Coconut Cove Resort and Marina

18. The Ocean View Inn & Pub

19. Matecumbe Resort

20. Treasure Harbor

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

beach near Islamorada

Keys History & Discovery Center

MoradaWay Arts & Cultural District

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Bayside Inn Key Largo

Islander Resort

Waterside Suites & Marina

Casa Morada

Playa Largo Resort & Spa, Autograph Collection

The Caribbean Resort

Pines & Palms Resort

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Breezy Palms Resort

Creekside Inn

Drift Hotel

Hampton Inn Key Largo Manatee Bay

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

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