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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,807 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is P9,628
P14,417 total
includes taxes & fees
Nov 3 - Nov 4
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, (1,500 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is P11,556
P17,662 total
includes taxes & fees
Nov 29 - Nov 30
Cheeca Lodge & Spa
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.

3. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is P4,406
P8,261 total
includes taxes & fees
Nov 3 - Nov 4
Breezy Palms Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,324 reviews)
"Great location as well."
United States
Amir
The price is P10,713
P16,714 total
includes taxes & fees
Nov 15 - Nov 16
Amara Cay Resort
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, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is P7,987
P10,778 total
includes taxes & fees
Nov 4 - Nov 5
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, (1,160 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is P14,788
P21,297 total
includes taxes & fees
Nov 3 - Nov 4
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)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is P9,121
P12,341 total
includes taxes & fees
Nov 16 - Nov 17
Hadley Resort and Marina
A beachfront property with colorful buildings, palm trees, and a sandy beach.

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 P9,853
P15,746 total
includes taxes & fees
Nov 16 - Nov 17
La Siesta Resort & Villas
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

9. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is P12,187
P17,224 total
includes taxes & fees
Nov 4 - Nov 5
Pines & Palms Resort
A two-story building with a balcony, surrounded by palm trees and a sandy ground.

10. 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 P12,238
P14,628 total
includes taxes & fees
Nov 16 - Nov 17
Sands of Islamorada
A resort with multiple buildings, a central pool, and a marina.

11. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is P15,298
P21,870 total
includes taxes & fees
Nov 3 - Nov 4
Bayside Villas by Islander Resort
A beachfront hotel with multiple-story buildings, a pool, and palm trees.

12. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is P43,598
P53,709 total
includes taxes & fees
Nov 30 - Dec 1
The Islands of Islamorada
A boat docked near a waterfront with a hammock and a chair, surrounded by greenery and palm trees.

13. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (466 reviews)
"Very helpful staff and great location"
United States
David
The price is P11,703
P13,883 total
includes taxes & fees
Nov 4 - Nov 5
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

Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Just a quick stay but was very comfortable."
Bryan 1-night trip
Posted less than an hour ago
Waterside Suites & Marina

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
4,777
Accommodation
0 Cabin Rentals
Lowest Price
P8,261
Highest Price
P53,709

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 P8,261 to P53,709 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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