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

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

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

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

1. Cheeca Lodge & Spa

Matecumbe

Morgan

5.148.528 ₫

7.684.112 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

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

2. Islander Resort

Matecumbe

Steven

5.671.142 ₫

8.271.797 ₫ total

includes taxes & fees

14 Oct - 15 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 beach with palm trees, a dock, and lounge chairs.

A resort pool with palm trees, beach chairs, and umbrellas.

3. Amara Cay Resort

Matecumbe

Danielle

3.999.164 ₫

6.391.078 ₫ 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 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.

4. Chesapeake Beach Resort

Matecumbe

Richard

3.907.966 ₫

5.851.762 ₫ total

includes taxes & fees

14 Oct - 15 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 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.

5. La Jolla Resort

Matecumbe

Brett

3.290.918 ₫

4.430.062 ₫ total

includes taxes & fees

13 Oct - 14 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 resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.

6. The Islands of Islamorada

Matecumbe

Christian

13.505.184 ₫

16.889.631 ₫ total

includes taxes & fees

13 Oct - 14 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 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.

7. Pines & Palms Resort

Matecumbe

Colt

4.424.112 ₫

6.403.450 ₫ total

includes taxes & fees

13 Oct - 14 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 beach scene with two yellow beach chairs and a person lying on one.

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

8. Hadley Resort and Marina

Matecumbe

weder

3.702.283 ₫

5.009.271 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

A row of colorful beach huts with palm trees in the background.

A beach with colorful buildings, kayaks, and lounge chairs.

9. La Siesta Resort & Villas

Matecumbe

Brianne

4.348.436 ₫

6.784.009 ₫ total

includes taxes & fees

8 Nov - 9 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 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.

10. Breezy Palms Resort

Matecumbe

Gavin

2.592.116 ₫

3.328.691 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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.

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

11. Bayside Villas by Islander Resort

Matecumbe

Brian

6.706.022 ₫

9.436.036 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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 beach with an American flag, palm trees, and a barbecue area.

12. Sands of Islamorada

Matecumbe

Nicolas

4.967.424 ₫

5.937.624 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

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

13. Casa Morada

Matecumbe

David

4.138.175 ₫

4.946.507 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

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

Islamorada

Liosbel

5.915.633 ₫

8.547.107 ₫ total

includes taxes & fees

18 Oct - 19 Oct

An aerial view of a resort with a large pool, palm trees, and a beach.

A beach with clear water, a wooden pier, and lounge chairs under a tree.

A beachside patio with lounge chairs, a table, and a view of the ocean.

A restaurant with wooden tables and chairs, a bar area, and a view of the sea.

15. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Tania

6.804.336 ₫

9.081.201 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

16. Lime Tree Bay Resort

Long Key

Michael

3.204.454 ₫

4.769.251 ₫ total

includes taxes & fees

13 Oct - 14 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 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.

17. Fisher Inn Resort & Marina

Islamorada

Siobhan

4.167.979 ₫

5.533.180 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

18. Atlantic Bay Resort

Tavernier

Annette

3.604.695 ₫

4.637.402 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

A hotel room with a bed, a TV, a sofa, and a balcony with a view.

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.

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

Key Largo

Omar Ahmad

2.538.043 ₫

3.675.699 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

A clear blue pool with lounge chairs and palm trees.

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

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

20. Hampton Inn Key Largo Manatee Bay

Key Largo

Samantha

3.351.976 ₫

3.770.974 ₫ total

includes taxes & fees

20 Oct - 21 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)

You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.

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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)

Learn about the local history of Islamorada when you take a trip to Hurricane Monument. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

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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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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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beach near Islamorada

Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?

See properties

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

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

10/10 Excellent

"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"

Hawks Cay Resort

10/10 Excellent

"Clean villas and very nice. Pool was great and the breakfast and tiki bar were nice. Staff were solid, but not amazing or over the top by any means which is fine for me but maybe not others. For example, took an hour and a second call to get towels because we were short one for someone to take a shower. Lots of cones on the roads and work going on but it is the off-season so they have to get it done at one point! Overall we had a great time!"

The Pelican Key Largo Cottages

8/10 Good

"Friendly, helpful staff. Great views of the sunset in Key Largo. Cute room & facility."

Breezy Palms Resort

10/10 Excellent

"Clean and spacious. Good location for what I wanted. Loved the mini kitchen inside."

Chesapeake Beach Resort

8/10 Good

"Great place"

Bayside Inn Key Largo

8/10 Good

"I stay at the Bayside Inn once a year while doing landscape photography in the Keys. Two issues bother me and will have me looking for a different place to stay next year. One, rooms aren't cleaned unless the guest asks / I stayed 9 days and no one had the professional courtesy to ask if I needed fresh towels or cleaning / I emptied my own trash. New policy or not about entering rooms, at these prices the front desk should pro actively call / text guests about needs. The second issue has to do with an additional amenity fee that is charged, other than my room, I use nothing else. I've asked about this but have never gotten a clear answer."

Lime Tree Bay Resort

10/10 Excellent

"Excellent"

Waterside Suites & Marina

10/10 Excellent

"It was a good value for the cost of the rental! It was comfortable and close to all of the restaurants and things that we like to do! We would definitely rent again!"

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."

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

1.974.033 ₫

2.220.787 ₫ total

27 Oct - 28 Oct

includes taxes & fees

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

2.460.056 ₫

2.767.563 ₫ total

13 Oct - 14 Oct

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

2.592.116 ₫

3.328.691 ₫ total

21 Oct - 22 Oct

includes taxes & fees

9/10 Wonderful! (767 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

3.027.024 ₫

3.405.531 ₫ total

20 Oct - 21 Oct

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

3.351.976 ₫

3.770.974 ₫ total

20 Oct - 21 Oct

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

3.559.211 ₫

4.003.951 ₫ total

12 Nov - 13 Nov

includes taxes & fees

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from 2.220.787 ₫

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. Amara Cay Resort

4. Chesapeake Beach Resort

5. La Jolla Resort

6. The Islands of Islamorada

7. Pines & Palms Resort

8. Hadley Resort and Marina

9. La Siesta Resort & Villas

10. Breezy Palms Resort

11. Bayside Villas by Islander Resort

12. Sands of Islamorada

13. Casa Morada

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

15. Playa Largo Resort & Spa, Autograph Collection

16. Lime Tree Bay Resort

17. Fisher Inn Resort & Marina

18. Atlantic Bay Resort

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

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

MoradaWay Arts & Cultural District

Lorelei Restaurant & Cabana Bar

beach near Islamorada

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

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

Hawks Cay Resort

The Pelican Key Largo Cottages

Breezy Palms Resort

Chesapeake Beach Resort

Bayside Inn Key Largo

Lime Tree Bay Resort

Waterside Suites & Marina

Pines & Palms Resort

More cheap stays in Upper Matecumbe Key

Rock Reef Resort

The Pelican Key Largo Cottages

Breezy Palms Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Explore a world of travel with Expedia

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