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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec
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, (1,761 reviews)
"Beautiful resort! Very tropical vibes! I would definitely stay here again!"
United States
Alisha
The price is Rp2.672.679
Rp4.002.052 total
includes taxes & fees
30 Aug - 31 Aug
Chesapeake Beach Resort
A courtyard with palm trees and flower beds, surrounded by buildings with balconies and a central entrance.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,417 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
The price is Rp2.644.452
Rp4.272.919 total
includes taxes & fees
2 Sept - 3 Sept
Cheeca Lodge & Spa
A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location and great staff"
United States
adrian
The price is Rp2.115.562
Rp2.879.258 total
includes taxes & fees
27 Aug - 28 Aug
La Jolla Resort
A resort with palm trees, a white building, and a sandy ground.

4. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,108 reviews)
"Staff and resort were amazing!"
United States
Chris
The price is Rp3.975.552
Rp5.670.486 total
includes taxes & fees
31 Aug - 1 Sept
Islander Resort
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

5. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"I had an excellent stay at the resort. and look forward to returning!"
United States
Isabel
The price is Rp3.109.450
Rp4.476.578 total
includes taxes & fees
30 Aug - 31 Aug
Pines & Palms 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.

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (729 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is Rp1.815.404
Rp2.324.638 total
includes taxes & fees
22 Sept - 23 Sept
Breezy Palms Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,294 reviews)
"Best place to stay !!"
United States
David A
The price is Rp2.973.920
Rp4.639.622 total
includes taxes & fees
16 Sept - 17 Sept
Amara Cay Resort
A building with a green roof and a sign that reads "Hadley House Oceanfront Resort."

8. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,013 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is Rp1.940.147
Rp2.760.020 total
includes taxes & fees
10 Sept - 11 Sept
Hadley Resort and Marina
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (457 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is Rp4.169.005
Rp5.888.120 total
includes taxes & fees
31 Aug - 1 Sept
Bayside Villas by Islander Resort
A row of colorful beach huts with palm trees in the background.

10. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,011 reviews)
"Great place to stay!"
United States
Brianne
The price is Rp2.735.051
Rp4.370.894 total
includes taxes & fees
27 Aug - 28 Aug
La Siesta Resort & Villas
A resort with multiple-story buildings, palm trees, and a well-maintained lawn.

11. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (80 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 Rp6.369.840
Rp8.268.848 total
includes taxes & fees
21 Sept - 22 Sept
The Islands of Islamorada
A two-story building with a balcony, surrounded by palm trees and a sandy ground.

12. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (414 reviews)
"Great place to stay!"
United States
Virginia
The price is Rp3.567.348
Rp4.252.953 total
includes taxes & fees
17 Sept - 18 Sept
Sands of Islamorada
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, (451 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is Rp2.930.126
Rp3.495.450 total
includes taxes & fees
31 Aug - 1 Sept
Casa Morada
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Amazing breakfast, clean room and very friendly staff."
Oleksandr 5-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
7,337
Accommodation
0 Cabin Rentals
Lowest Price
Rp2.324.638
Highest Price
Rp8.268.848

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 Rp2.324.638 to Rp8.268.848 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.