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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr
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, (1602)
"The entire resort was wonderful."
Canada
Mat
The price is NZ$413
includes taxes & fees
6 Jan - 7 Jan 2026
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
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
The price is NZ$322
includes taxes & fees
8 Jan - 9 Jan 2026
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
The price is NZ$972
includes taxes & fees
9 Jan - 10 Jan 2026
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
The price is NZ$531
includes taxes & fees
6 Jan - 7 Jan 2026
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
The price is NZ$405
includes taxes & fees
11 Jan - 12 Jan 2026
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
The price is NZ$345
includes taxes & fees
11 Jan - 12 Jan 2026
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
The price is NZ$870
includes taxes & fees
4 Jan - 5 Jan 2026
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
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
The price is NZ$459
includes taxes & fees
8 Jan - 9 Jan 2026
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
The price is NZ$375
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$1,277
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$626
includes taxes & fees
8 Jan - 9 Jan 2026
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
The price is NZ$712
includes taxes & fees
24 Dec - 25 Dec
Casa Morada
Exterior
Charming Suite @Islamorada With Pool Access - Twilight Suite

Aparthotel in Matecumbe

Charming Suite @Islamorada With Pool Access - Twilight Suite
The price is NZ$4,372
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$3,539
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$3,560
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$4,135
includes taxes & fees
1 Jan - 2 Jan 2026
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
The price is NZ$2,186
includes taxes & fees
5 Jan - 6 Jan 2026
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
The price is NZ$2,177
includes taxes & fees
1 Jan - 2 Jan 2026
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great chef that made breakfast to order! Resort was calming and relaxing! "
Sue 7-night trip
Posted 2 days ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
12,005
Accommodation
1 Cabin Rentals
Lowest Price
NZ$322
Highest Price
NZ$4,372

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 NZ$322 to NZ$4,372 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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