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Search cabins in Upper Matecumbe Key

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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, (1602)
"The entire resort was wonderful."
Canada
Mat
$231 nightly
The price is $260
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, (1000)
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
$147 nightly
The price is $165
Jan 14 - Jan 15, 2026
Total with taxes and fees
La Jolla 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
$156 nightly
The price is $175
Jan 8 - Jan 9, 2026
Total with taxes and fees
Sunset Inn
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
9.2 out of 10, Wonderful, (1002)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
$346 nightly
The price is $390
Jan 6 - Jan 7, 2026
Total with taxes and fees
Islander Resort
Aerial view
Amara Cay Resort

Resort in Matecumbe

Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1267)
"Friendly staff and beautiful property !"
United States
ron
$271 nightly
The price is $305
Jan 5 - Jan 6, 2026
Total with taxes and fees
Amara Cay Resort
Exterior
Breezy Palms Resort

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (590)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
$204 nightly
The price is $230
Dec 24 - Dec 25
Total with taxes and fees
Breezy Palms Resort
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
$178 nightly
The price is $200
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hadley Resort and Marina
Reception
Cheeca Lodge & Spa

Resort in Matecumbe

Cheeca Lodge & Spa
5.0 star property
9.2 out of 10, Wonderful, (1278)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
$361 nightly
The price is $407
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cheeca Lodge & Spa
Exterior
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (1001)
"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."
Canada
scott
$308 nightly
The price is $347
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pines & Palms 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, (1001)
"Great stay and beautiful space"
United States
Amir
$243 nightly
The price is $274
Jan 14 - Jan 15, 2026
Total with taxes and fees
La Siesta Resort & Villas
Exterior
Sands of Islamorada

Sands of Islamorada

Sands of Islamorada
2.5 star property
8.8 out of 10, Excellent, (392)
"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
$193 nightly
The price is $217
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sands of Islamorada
Aerial view
The Islands of Islamorada

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
$658 nightly
The price is $740
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Islands of Islamorada
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, (401)
"Beautiful stay!!!"
United States
Lakyne
$342 nightly
The price is $385
Jan 7 - Jan 8, 2026
Total with taxes and fees
Bayside Villas by Islander Resort
Exterior
Casa Morada

Casa Morada

Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (415)
"always a pleasant stay."
United States
robert
$389 nightly
The price is $438
Dec 24 - Dec 25
Total with taxes and fees
Casa Morada
Exterior
Charming Suite @Islamorada With Pool Access - Twilight Suite

Aparthotel in Matecumbe

Charming Suite @Islamorada With Pool Access - Twilight Suite
$2,274 nightly
The price is $2,524
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite
Exterior
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Aparthotel in Matecumbe

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
$1,843 nightly
The price is $2,045
Dec 30 - Dec 31
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Exterior
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Aparthotel in Matecumbe

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
$1,860 nightly
The price is $2,064
Dec 30 - Dec 31
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Exterior
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Aparthotel in Matecumbe

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
$2,165 nightly
The price is $2,402
Dec 30 - Dec 31
Total with taxes and fees
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
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 30 - Dec 31
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 30 - Dec 31
Total with taxes and fees
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"Beautiful chilled out hotel"
Jacqueline 2-night trip
Posted 8 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
12,001
Accommodation
1 Cabin Rentals
Lowest Price
$165
Highest Price
$2,524

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 $165 to $2,524 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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