A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Find Cheap Hotels in Upper Matecumbe Key, FL

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Check availability on Upper Matecumbe Key Cheap Hotels

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Upper Matecumbe Key cheap 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 spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Jessica
￥23,704
￥38,302 total
includes taxes & fees
Sep 2 - Sep 3
Cheeca Lodge & Spa
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.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Yeniaris
￥24,030
￥35,984 total
includes taxes & fees
Aug 30 - Aug 31
Chesapeake Beach Resort
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.
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.

3. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
￥17,444
￥24,815 total
includes taxes & fees
Sep 20 - Sep 21
Hadley Resort and Marina
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 beach with wooden lounge chairs, palm trees, and a clear 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.

4. La Jolla Resort

La Jolla Resort
Matecumbe
United States
adrian
￥18,977
￥25,827 total
includes taxes & fees
Aug 27 - Aug 28
La Jolla Resort
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 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.
An aerial view of a resort with a swimming pool, palm trees, and a dock.

5. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
David A
￥24,600
￥39,309 total
includes taxes & fees
Aug 30 - Aug 31
Amara Cay Resort
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 modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.
A beach with thatched umbrellas, palm trees, and lounge chairs.

6. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
United States
Orlando
￥16,167
￥20,724 total
includes taxes & fees
Sep 15 - Sep 16
Breezy Palms Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.
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.
A beachside resort with a pool area, lounge chairs, and palm trees.

7. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Isabel
￥23,777
￥35,520 total
includes taxes & fees
Aug 31 - Sep 1
Pines & Palms Resort
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 beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

8. Islander Resort

Islander Resort
Matecumbe
United States
Sonia
￥37,653
￥53,099 total
includes taxes & fees
Sep 22 - Sep 23
Islander Resort
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.
A resort with a pool surrounded by palm trees and a view of the ocean.
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.

9. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
￥24,592
￥39,300 total
includes taxes & fees
Aug 30 - Aug 31
La Siesta Resort & Villas
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 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.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
United States
beata
￥35,875
￥51,098 total
includes taxes & fees
Sep 1 - Sep 2
Bayside Villas by Islander Resort
View all properties

Top Upper Matecumbe Key Hotel Reviews

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"We had an amazing stay at Amara Cay Resort! The property was beautiful, clean, and relaxing, with an incredible waterfront setting and a true tropical Keys atmosphere. The staff was friendly, welcoming, and attentive throughout our entire stay. The pool and outdoor areas were perfect for relaxing, and the location made it easy to enjoy everything Islamorada has to offer. Overall, we had a fantastic experience and would absolutely recommend Amara Cay to anyone visiting the Florida Keys. We’re already looking forward to coming back!"
Nicolas 1-night trip
Posted 6 hours ago
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The views were great and the location was perfect. The staff was friendly and helpful."
orlando 1-night trip
Posted 7 hours ago
Chesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Clean room and staff"
Steve 3-night trip
Posted 8 hours ago
Waterside Suites & Marina
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Service and location"
Joe 2-night trip
Posted 10 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"Property is beautiful, staff is great and overall an amazing place to stay."
Sonia 1-night trip
Posted 12 hours ago
Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Wonderfully magical place that my wife and I enjoyed immensely! The beachfront bungalows were just perfect! Can't wait to see it again soon!"
stuart 4-night trip
Posted 2 days ago
La Siesta Resort & Villas
Pines & Palms Resort

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."
Arturo 3-night trip
Posted 2 days ago
Pines & Palms Resort

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