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

Find Cabins in Upper Matecumbe Key for Rent from CA $181

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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, (1,810 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is CA $196
CA $299 total
includes taxes & fees
Nov 10 - Nov 11
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, (1,503 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is CA $254
CA $387 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, (778 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $97
CA $181 total
includes taxes & fees
Nov 10 - Nov 11
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, (1,325 reviews)
"Great location as well."
United States
Amir
The price is CA $216
CA $346 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $175
CA $236 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, (1,161 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 CA $276
CA $413 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $188
CA $257 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $216
CA $345 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $267
CA $378 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $268
CA $321 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 CA $299
CA $438 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $897
CA $1,112 total
includes taxes & fees
Nov 23 - Nov 24
The Islands of Islamorada
A pool with a view of a bridge and umbrellas in the background.

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

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is CA $4,195
CA $5,077 total
includes taxes & fees
Nov 10 - Nov 11
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
A pool with a view of a bridge and umbrellas in the background.

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is CA $1,397
CA $1,692 total
includes taxes & fees
Nov 18 - Nov 19
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
A covered outdoor area with a white railing, a table with a straw hat, and a bench.

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is CA $2,276
CA $2,755 total
includes taxes & fees
Nov 10 - Nov 11
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
A pool with a view of a bridge and umbrellas in the background.

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is CA $2,797
CA $3,385 total
includes taxes & fees
Nov 10 - Nov 11
Charming Suite @Islamorada With Pool Access - Twilight Suite
A pool with a view of a bridge and umbrellas in the background.

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is CA $2,097
CA $2,539 total
includes taxes & fees
Nov 10 - Nov 11
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
A pool with a view of a bridge and umbrellas in the background.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is CA $2,264
CA $2,740 total
includes taxes & fees
Nov 10 - Nov 11
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
A boat docked near a waterfront with a hammock and a chair, surrounded by greenery and palm trees.

19. 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 CA $257
CA $304 total
includes taxes & fees
Dec 1 - Dec 2
Casa Morada
A pool with a view of a bridge and umbrellas in the background.

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is CA $2,794
CA $3,382 total
includes taxes & fees
Nov 10 - Nov 11
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Food was excellent and staff was extremely friendly. The room could have been a little better. The floors were sandy but the room was otherwise clean"
WILLIAM 2-night trip
Posted 19 hours ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
4,003
Accommodation
2 Cabin Rentals
Lowest Price
CA $181
Highest Price
CA $5,077

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 CA $181 to CA $5,077 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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