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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

Water view

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,760 reviews)
"Spectacular, beautiful view, excellent amenities, a quiet and beautiful place, very attentive staff, and the breakfast is exquisite—I’ll be back as soon as I can"
United States
alicia
The price is AU$317
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Beach Resort
Reception

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,360 reviews)
"I was an excellent vacation."
United States
Yuniel
The price is AU$344
includes taxes & fees
18 Aug - 19 Aug
Cheeca Lodge & Spa
Exterior

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,084 reviews)
"Can't wait to stay there again!"
United States
Sarah
The price is AU$495
includes taxes & fees
30 Aug - 31 Aug
Islander Resort
Exterior

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Good location and great staff"
United States
adrian
The price is AU$219
includes taxes & fees
18 Aug - 19 Aug
La Jolla Resort
Exterior

5. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Property was very kept up, room was very clean. Staff was very helpful and kind."
United States
John
The price is AU$394
includes taxes & fees
31 Aug - 1 Sept
Pines & Palms Resort
Dock

6. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (454 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is AU$482
includes taxes & fees
12 Aug - 13 Aug
Bayside Villas by Islander Resort
Suite, 1 King Bed with Sofa bed, Ocean View | Exterior

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,003 reviews)
"Great place to stay!"
United States
Brianne
The price is AU$352
includes taxes & fees
23 Aug - 24 Aug
La Siesta Resort & Villas
Aerial view

8. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,294 reviews)
"Beautiful hotel, amazing views , very friendly staff, I will definitely return to Amara cay"
United States
Estefani
The price is AU$355
includes taxes & fees
2 Sept - 3 Sept
Amara Cay Resort
Exterior

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is AU$236
includes taxes & fees
30 Aug - 31 Aug
Hadley Resort and Marina
Exterior

10. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (717 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is AU$235
includes taxes & fees
10 Aug - 11 Aug
Breezy Palms Resort
Property grounds

11. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (79 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is AU$592
includes taxes & fees
16 Aug - 17 Aug
The Islands of Islamorada
Exterior

12. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (414 reviews)
"Great place to stay!"
United States
Virginia
The price is AU$365
includes taxes & fees
18 Aug - 19 Aug
Sands of Islamorada
Exterior

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is AU$1,782
includes taxes & fees
11 Aug - 12 Aug
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Terrace/patio

14. Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
The price is AU$1,750
includes taxes & fees
12 Aug - 13 Aug
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Exterior

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is AU$2,633
includes taxes & fees
16 Aug - 17 Aug
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is AU$2,849
includes taxes & fees
16 Aug - 17 Aug
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Exterior

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is AU$2,841
includes taxes & fees
15 Aug - 16 Aug
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Exterior

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

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is AU$5,344
includes taxes & fees
11 Aug - 12 Aug
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Exterior

19. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (448 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is AU$433
includes taxes & fees
19 Aug - 20 Aug
Casa Morada
Exterior

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is AU$3,559
includes taxes & fees
11 Aug - 12 Aug
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

Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"El lugar es excelente ,bien limpio y renovado"
Jesus 2-night trip
Posted 9 hours ago
Pines & Palms Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
5,865
Accommodation
2 Cabin Rentals
Lowest Price
AU$219
Highest Price
AU$5,344

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 AU$219 to AU$5,344 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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