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Search cabins in Upper Matecumbe Key

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

Water view
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
9.2 out of 10, Wonderful, (1589)
"Great breakfast, great location, friendly staff, nice extras."
United States
Gary
$221 nightly
The price is $249
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chesapeake Beach Resort
Exterior
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
9.0 out of 10, Wonderful, (1003)
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
$125 nightly
The price is $141
Dec 18 - Dec 19
Total with taxes and fees
La Jolla Resort
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
9.2 out of 10, Wonderful, (1002)
"This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike. "
United States
Suzanne
$311 nightly
The price is $350
Jan 6 - Jan 7, 2026
Total with taxes and fees
Islander Resort
Reception
Cheeca Lodge & Spa

Resort in Matecumbe

Cheeca Lodge & Spa
5.0 star property
9.2 out of 10, Wonderful, (1268)
"It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!"
United States
Sami
$245 nightly
The price is $276
Dec 16 - Dec 17
Total with taxes and fees
Cheeca Lodge & Spa
Exterior
Breezy Palms Resort

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (584)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
$146 nightly
The price is $164
Dec 17 - Dec 18
Total with taxes and fees
Breezy Palms Resort
Property grounds
Sunset Inn

Sunset Inn

Sunset Inn
3.0 star property
9.4 out of 10, Exceptional, (1000)
"Room was clean and staff was helpful"
United States
Robert
$148 nightly
The price is $166
Dec 16 - Dec 17
Total with taxes and fees
Sunset Inn
Aerial view
Amara Cay Resort

Resort in Matecumbe

Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1262)
"very nice staff, quiet and comfortable"
United States
Dana
$226 nightly
The price is $255
Dec 18 - Dec 19
Total with taxes and fees
Amara Cay Resort
Suite, 1 King Bed with Sofa bed, Ocean View | Exterior
La Siesta Resort & Villas

Resort in Matecumbe

La Siesta Resort & Villas
4.0 star property
8.8 out of 10, Excellent, (1000)
"Great stay and beautiful space"
United States
Amir
$218 nightly
The price is $246
Dec 17 - Dec 18
Total with taxes and fees
La Siesta Resort & Villas
Exterior
Hadley Resort and Marina

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
7.6 out of 10, Good, (1000)
"Comfortable stay. Great location. "
United States
Anand
$160 nightly
The price is $180
Dec 16 - Dec 17
Total with taxes and fees
Hadley Resort and Marina
Exterior
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (1001)
"Very nice place to stay "
United States
Joan
$248 nightly
The price is $279
Dec 15 - Dec 16
Total with taxes and fees
Pines & Palms Resort
Dock
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
8.8 out of 10, Excellent, (400)
"I loved the property, the staff and all the amenities."
United States
Janeth
$321 nightly
The price is $362
Dec 15 - Dec 16
Total with taxes and fees
Bayside Villas by Islander Resort
Aerial view
The Islands of Islamorada

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
United States
Dixania
$593 nightly
The price is $667
Dec 15 - Dec 16
Total with taxes and fees
The Islands of Islamorada
Exterior
Casa Morada

Casa Morada

Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (413)
"always a pleasant stay."
United States
robert
$398 nightly
The price is $448
Dec 15 - Dec 16
Total with taxes and fees
Casa Morada
Exterior
Sands of Islamorada

Sands of Islamorada

Sands of Islamorada
2.5 star property
8.8 out of 10, Excellent, (391)
"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
$195 nightly
The price is $219
Dec 14 - Dec 15
Total with taxes and fees
Sands of Islamorada
Exterior
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Aparthotel in Matecumbe

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
$1,142 nightly
The price is $1,267
Dec 20 - Dec 21
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Terrace/patio
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Aparthotel in Matecumbe

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
$1,142 nightly
The price is $1,267
Dec 20 - Dec 21
Total with taxes and fees
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Exterior
Charming Suite @Islamorada With Pool Access - Twilight Suite

Aparthotel in Matecumbe

Charming Suite @Islamorada With Pool Access - Twilight Suite
$2,284 nightly
The price is $2,534
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite
Exterior
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Aparthotel in Matecumbe

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
$2,160 nightly
The price is $2,397
Dec 20 - Dec 21
Total with taxes and fees
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Exterior
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Aparthotel in Matecumbe

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
$1,706 nightly
The price is $1,894
Dec 20 - Dec 21
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Aparthotel in Matecumbe

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
$1,841 nightly
The price is $2,043
Dec 20 - Dec 21
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee 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

Casa Morada

Casa Morada

10/10 Excellent
"Room was clean. Facility beautiful. Staff wonderful!"
Michael 3-night trip
Posted 2 days ago
Casa Morada

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
11,977
Accommodation
1 Cabin Rentals
Lowest Price
$141
Highest Price
$2,534

Frequently asked questions

Are there cheap cabins in Upper Matecumbe Key?
For a nicely priced getaway in Mother Nature, have a look at our cheap cabins in Upper Matecumbe Key. Awake to the sound of birds chirping from one of our cozy cabins priced from $141 to $2,534 a night. 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 best weekend cabin rentals in Upper Matecumbe Key?
If you can't wait to spend two or so restful days surrounded by Mother Nature, Cabin - Sand Is The New Snow - New 4bedroom W will check all your boxes. Stay here for a weekend and make use of amenities such as a private pool and a deck. Another terrific escape is Historic, Dog - Friendly Cottage In The Heart Of Key West W. Offering a patio, a deck and lots of peace and quiet, you'll go home feeling refreshed and energized.
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?
For a nature-filled getaway at the perfect price, you can't go past a cabin. Picture yourself waking up to the sound of birds outside and having breakfast on your deck surrounded by dreamy views. Choose a cabin in Upper Matecumbe Key and say goodbye to the busyness of the city. Whether they're by a lake, river, beach or mountain, cabins offer a rustic and relaxing experience for those who need a break.
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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