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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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 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.

1. Islander Resort

Matecumbe

Steven

฿6,996

฿10,330 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 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.

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

2. Cheeca Lodge & Spa

Matecumbe

Morgan

฿6,693

฿9,990 total

includes taxes & fees

19 Oct - 20 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 hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

3. Chesapeake Beach Resort

Matecumbe

Phelicia

฿5,081

฿7,608 total

includes taxes & fees

18 Oct - 19 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 resort pool with palm trees, beach chairs, and umbrellas.

4. Amara Cay Resort

Matecumbe

Danielle

฿5,199

฿8,309 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 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.

5. La Jolla Resort

Matecumbe

Brett

฿4,813

฿6,361 total

includes taxes & fees

22 Oct - 23 Oct

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

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.

A beach scene with two yellow beach chairs and a person lying on one.

6. Hadley Resort and Marina

Matecumbe

weder

฿4,813

฿6,512 total

includes taxes & fees

9 Nov - 10 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 beach with palm trees, a wooden pier, and beach chairs.

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.

7. Pines & Palms Resort

Matecumbe

Colt

฿6,932

฿9,653 total

includes taxes & fees

21 Oct - 22 Oct

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

A resort with a pool surrounded by palm trees and a view of the ocean.

8. La Siesta Resort & Villas

Matecumbe

Brianne

฿5,199

฿8,309 total

includes taxes & fees

15 Nov - 16 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 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.

9. Breezy Palms Resort

Matecumbe

Gavin

฿3,300

฿4,249 total

includes taxes & fees

18 Oct - 19 Oct

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.

10. The Islands of Islamorada

Matecumbe

Christian

฿17,522

฿21,913 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

11. Bayside Villas by Islander Resort

Matecumbe

Brian

฿8,701

฿12,243 total

includes taxes & fees

27 Oct - 28 Oct

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

12. Sands of Islamorada

Matecumbe

Nicolas

฿6,411

฿7,666 total

includes taxes & fees

22 Oct - 23 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

David

฿5,257

฿6,291 total

includes taxes & fees

27 Oct - 28 Oct

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

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

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

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

Islamorada

Liosbel

฿8,046

฿11,511 total

includes taxes & fees

3 Nov - 4 Nov

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

A tropical garden with palm trees, various colorful plants, and a seating area with chairs.

A hotel room with a kitchenette, two beds, a desk, a television, and a ceiling fan.

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

15. Hampton Inn Key Largo Manatee Bay

Key Largo

Samantha

฿4,386

฿4,934 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

A paved pathway leading to a body of water, surrounded by lush greenery and palm trees.

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

Key Largo

Omar Ahmad

฿3,595

฿5,109 total

includes taxes & fees

27 Oct - 28 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.

17. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

฿5,001

฿5,627 total

includes taxes & fees

27 Oct - 28 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 spacious living area with a large island, wooden furniture, and a ceiling fan.

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

18. Lime Tree Bay Resort

Long Key

Michael

฿4,158

฿6,188 total

includes taxes & fees

1 Nov - 2 Nov

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

฿4,186

฿5,466 total

includes taxes & fees

25 Oct - 26 Oct

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

20. Fisher Inn Resort & Marina

Islamorada

Siobhan

฿5,348

฿7,114 total

includes taxes & fees

19 Oct - 20 Oct

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Hotels recommended for families in Upper Matecumbe Key

Islander Resort

Matecumbe

฿6,996

฿10,330 total

includes taxes & fees

18 Oct - 19 Oct

Amara Cay Resort

Matecumbe

฿5,199

฿8,309 total

includes taxes & fees

18 Oct - 19 Oct

La Jolla Resort

Matecumbe

฿4,813

฿6,361 total

includes taxes & fees

22 Oct - 23 Oct

Cheeca Lodge & Spa

Matecumbe

฿6,693

฿9,990 total

includes taxes & fees

19 Oct - 20 Oct

Breezy Palms Resort

Matecumbe

฿3,300

฿4,249 total

includes taxes & fees

18 Oct - 19 Oct

Hadley Resort and Marina

Matecumbe

฿4,813

฿6,512 total

includes taxes & fees

9 Nov - 10 Nov

Pines & Palms Resort

Matecumbe

฿6,932

฿9,653 total

includes taxes & fees

21 Oct - 22 Oct

La Siesta Resort & Villas

Matecumbe

฿5,199

฿8,309 total

includes taxes & fees

15 Nov - 16 Nov

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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

Waterside Suites & Marina

10/10 Excellent

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

Breezy Palms Resort

8/10 Good

"The property was clean and extremely well lit. The parking was great. The room had a full kitchen which was a huge plus. The layout of the room and the furnishings were beautiful and up to date. The room was spacious and comfortable. The staff were friendly and hospitable. I didnt pay much attention when booking but free kayaks or bikes would have been a great additional amenity. I thought it was extra convenient to have boats for rent on property. This was also an added benefit. I will definitely stay here again in the future."

Bayside Inn Key Largo

10/10 Excellent

"Fabulous resort, great arrangement with Snook bar next door. The bantams were intriguing. Room good, but, dirty pair of underpants left in a draw by a previous guest."