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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

Rp2.632.681

Rp4.253.900 total

includes taxes & fees

29 Sept - 30 Sept

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

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

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.

2. Islander Resort

Matecumbe

Sonia

Rp3.919.868

Rp5.602.510 total

includes taxes & fees

27 Sept - 28 Sept

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.

3. La Jolla Resort

Matecumbe

Tamara

Rp1.931.046

Rp2.667.824 total

includes taxes & fees

22 Sept - 23 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 pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

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

4. Hadley Resort and Marina

Matecumbe

RAIBEL

Rp2.237.779

Rp3.094.041 total

includes taxes & fees

16 Sept - 17 Sept

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

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.

5. Bayside Villas by Islander Resort

Matecumbe

beata

Rp3.458.707

Rp5.083.703 total

includes taxes & fees

23 Sept - 24 Sept

A beach with palm trees and lounge chairs.

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

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.

6. Chesapeake Beach Resort

Matecumbe

Suresh

Rp2.660.142

Rp3.983.279 total

includes taxes & fees

28 Sept - 29 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.

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.

7. Amara Cay Resort

Matecumbe

Amy

Rp2.722.220

Rp4.350.389 total

includes taxes & fees

23 Sept - 24 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 modern two-story beachfront property with balconies, a pool, and a sandy beach area.

8. Pines & Palms Resort

Matecumbe

Stephen

Rp3.180.420

Rp4.552.064 total

includes taxes & fees

16 Sept - 17 Sept

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.

9. Breezy Palms Resort

Matecumbe

Lourdes

Rp1.447.444

Rp1.910.196 total

includes taxes & fees

16 Sept - 17 Sept

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 two-story building with a balcony, surrounded by palm trees and a sandy ground.

10. Sands of Islamorada

Matecumbe

Virginia

Rp3.198.089

Rp3.836.470 total

includes taxes & fees

16 Sept - 17 Sept

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 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.

11. The Islands of Islamorada

Matecumbe

Christian

Rp7.132.455

Rp9.137.467 total

includes taxes & fees

28 Sept - 29 Sept

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.

12. Casa Morada

Matecumbe

Lois

Rp2.795.908

Rp3.344.171 total

includes taxes & fees

7 Oct - 8 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 covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

A man standing next to a boat on a wooden dock with a chain barrier, palm trees, and a building in the background.

13. Fisher Inn Resort & Marina

Islamorada

Alexandra

Rp2.080.740

Rp2.915.479 total

includes taxes & fees

23 Sept - 24 Sept

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

A modern living room with a sofa, a glass coffee table, a TV, and a sliding door leading to a bedroom.

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

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

14. Drift Hotel

Key Largo

Sheily

Rp1.651.031

Rp2.055.534 total

includes taxes & fees

16 Sept - 17 Sept

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

A waterfront pier with wooden posts and a wooden walkway extending into the water.

A balcony with a view of the sea, a beach, and a thatched hut.

A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.

15. Sunset Cove Beach Resort

Key Largo

Douglas

Rp1.733.329

Rp1.950.128 total

includes taxes & fees

16 Sept - 17 Sept

A multi-story hotel with balconies, palm trees, and a view of the water.

A beachside area with palm trees, a wooden bench, and a wheelchair-accessible sign.

A spacious lobby with a reception desk, seating area, and a large aquarium display.

A marina with boats docked, surrounded by palm trees.

16. Marina Del Mar Resort and Marina

Key Largo

Francisco

Rp2.402.816

Rp3.198.608 total

includes taxes & fees

28 Sept - 29 Sept

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 sunset over a calm body of water with a dock and lounge chairs.

17. Seafarer Key Largo

Rock Harbor

Susan

Rp1.766.383

Rp2.234.837 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

18. Rock Reef Resort

Rock Harbor

Tia

Rp1.782.459

Rp2.005.266 total

includes taxes & fees

27 Sept - 28 Sept

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.

19. Hampton Inn Key Largo Manatee Bay

Key Largo

Susanna

Rp2.296.122

Rp2.583.138 total

includes taxes & fees

24 Sept - 25 Sept

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 resort with a pool, multiple buildings, and a waterfront view.

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

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

Key Largo

Omar Ahmad

Rp1.574.308

Rp2.331.380 total

includes taxes & fees

21 Sept - 22 Sept

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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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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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MoradaWay Arts & Cultural District

Enjoy an outing to MoradaWay Arts & Cultural District during your stay 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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Learn more about Upper Matecumbe Key

Venture to sights like Bud n' Mary's Dive Center and Lorelei Restaurant & Cabana Bar as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key

A beachside café with colorful chairs and tables, palm trees, and a view of the ocean.

Top Upper Matecumbe Key Hotel Reviews

Hawks Cay Resort

10/10 Excellent

"Beautiful resort"

Hadley Resort and Marina

8/10 Good

"Great location and good rates for the 2 nights that we stayed. Staff was great and helpful. Closed to shops, cafe, and restaurants."

Breezy Palms Resort

10/10 Excellent

"Great place... it is not fancy but it is comfortable, spacious, pool is clean, well located.... I can come back anytime"

Playa Largo Resort & Spa, Autograph Collection

8/10 Good

"Lovely hotel. Very expensive just to buy drinks though but good location."

Cheeca Lodge & Spa

10/10 Excellent

"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained."

Waterside Suites & Marina

10/10 Excellent

"1"

Chesapeake Beach Resort

10/10 Excellent

"/"

The Pelican Key Largo Cottages

10/10 Excellent

"It’s the perfect stay for a relaxing beach getaway."

La Jolla Resort

10/10 Excellent

"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t recommend this place more. It’s like a throwback to an earlier time, but completely updated. Plenty of restaurants to pick from nearby and the Islamorada Brewery across the street is great, and has a wonderful beer garden out back."

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

Rp1.659.667

Rp1.867.125 total

21 Sept - 22 Sept

includes taxes & fees

9/10 Wonderful! (1,003 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

Rp1.733.329

Rp1.950.128 total

16 Sept - 17 Sept

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

Rp1.782.459

Rp2.005.266 total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,185 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

Rp2.296.122

Rp2.583.138 total

24 Sept - 25 Sept

includes taxes & fees

8.8/10 Excellent! (1,087 reviews)

Creekside Inn

90611 Old Highway Tavernier FL

Rp2.326.124

Rp2.616.779 total

27 Sept - 28 Sept

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

Rp2.402.816

Rp3.198.608 total

28 Sept - 29 Sept

includes taxes & fees

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from Rp1.610.088

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. La Jolla Resort

4. Hadley Resort and Marina

5. Bayside Villas by Islander Resort

6. Chesapeake Beach Resort

7. Amara Cay Resort

8. Pines & Palms Resort

9. Breezy Palms Resort

10. Sands of Islamorada

11. The Islands of Islamorada

12. Casa Morada

13. Fisher Inn Resort & Marina

14. Drift Hotel

15. Sunset Cove Beach Resort

16. Marina Del Mar Resort and Marina

17. Seafarer Key Largo

18. Rock Reef Resort

19. Hampton Inn Key Largo Manatee Bay

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

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

MoradaWay Arts & Cultural District

beach near Islamorada

Keys History & Discovery Center

Learn more about Upper Matecumbe Key

Top Upper Matecumbe Key Hotel Reviews

Hawks Cay Resort

Hadley Resort and Marina

Breezy Palms Resort

Playa Largo Resort & Spa, Autograph Collection

Cheeca Lodge & Spa

Waterside Suites & Marina

Chesapeake Beach Resort

The Pelican Key Largo Cottages

La Jolla Resort

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Sunset Cove Beach Resort

Rock Reef Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Explore a world of travel with Expedia

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