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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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

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

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,795 reviews)
"Great place"
United States
Richard
The price is €202
includes taxes & fees
13 Oct - 14 Oct
Chesapeake Beach Resort
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.

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (762 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is €116
includes taxes & fees
21 Oct - 22 Oct
Breezy Palms Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock.

3. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,319 reviews)
"Super clean resort."
United States
Danielle
The price is €221
includes taxes & fees
18 Oct - 19 Oct
Amara Cay Resort
A courtyard with palm trees and flower beds, surrounded by buildings with balconies and a central entrance.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,472 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
The price is €255
includes taxes & fees
13 Oct - 14 Oct
Cheeca Lodge & Spa
A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

5. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,006 reviews)
"Nice hotel."
United States
Brett
The price is €153
includes taxes & fees
13 Oct - 14 Oct
La Jolla Resort
A resort with palm trees, a white building, and a sandy ground.

6. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,134 reviews)
"Amazing place would definitely recommend"
United States
Steven
The price is €327
includes taxes & fees
20 Oct - 21 Oct
Islander Resort
A building with a green roof and a sign that reads "Hadley House Oceanfront Resort."

7. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Great place"
United States
weder
The price is €173
includes taxes & fees
9 Nov - 10 Nov
Hadley Resort and Marina
A row of colorful beach huts with palm trees in the background.

8. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
The price is €234
includes taxes & fees
8 Nov - 9 Nov
La Siesta Resort & Villas
A resort with multiple-story buildings, palm trees, and a well-maintained lawn.

9. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (81 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is €582
includes taxes & fees
14 Oct - 15 Oct
The Islands of Islamorada
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

10. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
The price is €256
includes taxes & fees
21 Oct - 22 Oct
Pines & Palms Resort
A two-story building with a balcony, surrounded by palm trees and a sandy ground.

11. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
United States
Nicolas
The price is €205
includes taxes & fees
19 Oct - 20 Oct
Sands of Islamorada
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

12. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (466 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is €325
includes taxes & fees
21 Oct - 22 Oct
Bayside Villas by Islander Resort
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

13. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (462 reviews)
"Very helpful staff and great location"
United States
David
The price is €171
includes taxes & fees
28 Oct - 29 Oct
Casa Morada
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

14. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

15. Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
Charming Suite @Islamorada With Pool Access - Twilight Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

16. Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

17. Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

18. Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

19. Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

20. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Our room was very clean. Resort staff was super nice and accommodating. Amenities were nice. Pools were clean. Resort was very peaceful."
Grayson 5-night trip
Posted 15 hours ago
Islander Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
5,093
Accommodation
2 Cabin Rentals
Lowest Price
€116
Highest Price
€582

Frequently asked questions

Are there cheap cabins in Upper Matecumbe Key?
Whether you want to stay steps from the water or on the top of a mountain, we have an awesome variety of cheap cabins in Upper Matecumbe Key to suit your budget and taste. Priced from €116 to €582 per night, your ideal cabin is waiting right here. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the highest-rated cabins in Upper Matecumbe Key?
Expedia cabin travelers just keep coming back to Cabin - Sand Is The New Snow - New 4bedroom W. This top pick features a host of handy amenities including a private pool and a deck. It won't take you very long to see why Historic, Dog - Friendly Cottage In The Heart Of Key West W is also popular with vacationers. Conveniences such as a patio and a deck will help make your stay nice and comfortable.
Why should I book a cabin in Upper Matecumbe Key?
Affordability, outdoor attractions, rustic charm — there are countless great reasons to book an Upper Matecumbe Key cabin. Escape the noisy concrete jungle and wake up to the beautiful sounds of Mother Nature. There's so much adventure just around the corner too. Whether you're taking a break with friends, family or your partner, you'll find the perfect rental cabin on Expedia.
What are the top nature cabins in Upper Matecumbe Key?
Spend a few nights at Cabin - Sand Is The New Snow - New 4bedroom W and you'll be surrounded by nature. Amenities like a private pool and a deck help make this river cabin in Upper Matecumbe Key a top option. Historic, Dog - Friendly Cottage In The Heart Of Key West W is another place where you can escape the hustle and bustle and catch a few mindful moments by the water. Some of the conveniences here include a patio and a deck.

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