Book The Best Hotels in Upper Matecumbe Key, FL for 2026 from CA $145 - Fully Refundable Options

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

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

1. Cheeca Lodge & Spa

Matecumbe

RAIBEL

CA $180

CA $306 total

includes taxes & fees

Oct 4 - Oct 5

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A beach with wooden lounge chairs, 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 bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

2. La Jolla Resort

Matecumbe

CA $136

CA $193 total

includes taxes & fees

Sep 28 - Sep 29

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 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

Suresh

CA $202

CA $306 total

includes taxes & fees

Sep 29 - Sep 30

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 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.

4. Islander Resort

Matecumbe

John

CA $275

CA $405 total

includes taxes & fees

Sep 30 - Oct 1

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

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

5. Pines & Palms Resort

Matecumbe

Colt

CA $165

CA $263 total

includes taxes & fees

Sep 24 - Sep 25

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.

6. Amara Cay Resort

Matecumbe

MICHAEL

CA $204

CA $333 total

includes taxes & fees

Sep 27 - Sep 28

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.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

7. Hadley Resort and Marina

Matecumbe

CA $166

CA $233 total

includes taxes & fees

Sep 28 - Sep 29

A beach with palm trees, thatched-roof huts, and lounge 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.

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

8. Breezy Palms Resort

Matecumbe

Debra

CA $115

CA $152 total

includes taxes & fees

Oct 4 - Oct 5

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.

9. Bayside Villas by Islander Resort

Matecumbe

beata

CA $312

CA $446 total

includes taxes & fees

Sep 30 - Oct 1

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.

10. Casa Morada

Matecumbe

David

CA $220

CA $263 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

11. Sands of Islamorada

Matecumbe

Nicolas

CA $269

CA $322 total

includes taxes & fees

Oct 14 - Oct 15

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

A pool area with clear blue water, white lounge chairs, and palm trees.

12. The Islands of Islamorada

Matecumbe

Christian

CA $570

CA $730 total

includes taxes & fees

Oct 1 - Oct 2

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

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

13. Fisher Inn Resort & Marina

Islamorada

Alexandra

CA $166

CA $233 total

includes taxes & fees

Sep 24 - Sep 25

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.

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

Eslita

CA $280

CA $418 total

includes taxes & fees

Sep 29 - Sep 30

A beachside patio with white furniture, palm trees, and a thatched umbrella.

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.

A beach with palm trees, a thatched umbrella, and lounge chairs.

15. Drop Anchor

Islamorada

Marianela

CA $168

CA $238 total

includes taxes & fees

Sep 24 - Sep 25

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

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

A resort with thatched-roof structures, palm trees, and a sandy beach area.

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

16. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

CA $203

CA $229 total

includes taxes & fees

Sep 29 - Sep 30

A beach with rows of sun loungers and palm trees.

Three Adirondack chairs facing a sunset over a body of water.

A spacious room with a high ceiling, a ceiling fan, a dining table with chairs, a sofa, and a television mounted on the wall.

A clear blue swimming pool with a metal railing, surrounded by palm trees and a view of the ocean.

17. Ragged Edge Resort & Marina

Islamorada

Nathalie

CA $189

CA $213 total

includes taxes & fees

Sep 27 - Sep 28

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

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

18. Rock Reef Resort

Rock Harbor

Tia

CA $130

CA $147 total

includes taxes & fees

Sep 24 - Sep 25

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.

19. Lime Tree Bay Resort

Long Key

milayda

CA $162

CA $246 total

includes taxes & fees

Oct 6 - Oct 7

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

A sign for Matecumbe Resort with a full kitchen and heated pool.

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

A compact kitchen with modern appliances, a dining area with a sofa, and a large window providing natural light.

20. Matecumbe Resort

Matecumbe

paul

CA $175

CA $197 total

includes taxes & fees

Sep 24 - Sep 25

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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 exploring the galleries in Keys History & Discovery Center during your trip to Islamorada.

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Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Lorelei Restaurant & Cabana Bar.

See all hotels in Upper Matecumbe Key

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

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."

Breezy Palms Resort

10/10 Excellent

"Fantastic place, so clean and the room is beautiful. Gorgeous view!! Love this place!"

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"

Islander Resort

10/10 Excellent

"Loved the property!!! So quiet and relaxing! Great bar, pools, beaches!!!! Would absolutely stay again!"

Amara Cay Resort

8/10 Good

"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"

Lime Tree Bay Resort

8/10 Good

"Breakfast at on-site restaurant, average and overpriced. When we checked in our room, garbage left in cans from previous tenants."

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"Todo perfecto solo q en los Restaurantes no hay desayuno incluido, y los Plato’s están por en ima de la media de sus precios y en realidad no vale la pens pagarlos en ima de eso se demoran mucho"

Casa Morada

10/10 Excellent

"Very helpful staff and great location"

The Pelican Key Largo Cottages

10/10 Excellent

"The Pelican is a darling spot! Lots of space, convenient parking right next to our door, beautiful sandy beach area, well maintained dock, plenty of comfy Adirondack chairs in multiple spots to watch the water - the boats, fish, birds, and manatees. We really enjoyed the use of kayaks as well. Just a lovely property and stay."

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL

CA $129

CA $145 total

Oct 1 - Oct 2

includes taxes & fees

9/10 Wonderful! (1,002 reviews)

Rock Reef Resort

97850 Overseas Hwy Key Largo FL

CA $130

CA $147 total

Sep 24 - Sep 25

includes taxes & fees

9.2/10 Wonderful! (1,187 reviews)

Sunset Cove Beach Resort

MM 99.5 Key Largo FL

CA $164

CA $185 total

Oct 12 - Oct 13

includes taxes & fees

9.2/10 Wonderful! (1,009 reviews)

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL

CA $183

CA $206 total

Oct 11 - Oct 12

includes taxes & fees

Creekside Inn

90611 Old Highway Tavernier FL

CA $201

CA $226 total

Oct 8 - Oct 9

includes taxes & fees

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL

CA $191

CA $254 total

Sep 26 - Sep 27

includes taxes & fees

8.6/10 Excellent! (1,870 reviews)

Hotels in Upper Matecumbe Key with star rating

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Book Hotels in Upper Matecumbe Key on Expedia.com

Find hotels in Upper Matecumbe Key, FL from CA $145

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. La Jolla Resort

3. Chesapeake Beach Resort

4. Islander Resort

5. Pines & Palms Resort

6. Amara Cay Resort

7. Hadley Resort and Marina

8. Breezy Palms Resort

9. Bayside Villas by Islander Resort

10. Casa Morada

11. Sands of Islamorada

12. The Islands of Islamorada

13. Fisher Inn Resort & Marina

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

15. Drop Anchor

16. Coconut Cove Resort and Marina

17. Ragged Edge Resort & Marina

18. Rock Reef Resort

19. Lime Tree Bay Resort

20. Matecumbe Resort

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

Chesapeake Beach Resort

Breezy Palms Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Islander Resort

Amara Cay Resort

Lime Tree Bay Resort

Playa Largo Resort & Spa, Autograph Collection

Casa Morada

The Pelican Key Largo Cottages

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

Rock Reef Resort

Sunset Cove Beach Resort

Hampton Inn Key Largo Manatee Bay

Creekside Inn

Marina Del Mar Resort and Marina

Hotels in Upper Matecumbe Key with star rating

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