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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

Exterior

1. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
United States
Tamara
The price is AU$142
includes taxes & fees
5 Oct - 6 Oct
La Jolla Resort
Reception

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,431 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is AU$321
includes taxes & fees
30 Sept - 1 Oct
Cheeca Lodge & Spa
Exterior

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,119 reviews)
"Property is beautiful, staff is great and overall an amazing place to stay."
United States
Sonia
The price is AU$406
includes taxes & fees
30 Sept - 1 Oct
Islander Resort
Water view

4. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,776 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is AU$306
includes taxes & fees
28 Sept - 29 Sept
Chesapeake Beach Resort
Exterior

5. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (748 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is AU$139
includes taxes & fees
30 Sept - 1 Oct
Breezy Palms Resort
Aerial view

6. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,310 reviews)
"amazing clean stay."
United States
MICHAEL
The price is AU$325
includes taxes & fees
24 Sept - 25 Sept
Amara Cay Resort
Exterior

7. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."
United States
Stephen
The price is AU$389
includes taxes & fees
21 Sept - 22 Sept
Pines & Palms Resort
Dock

8. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (462 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is AU$446
includes taxes & fees
28 Sept - 29 Sept
Bayside Villas by Islander Resort
Exterior

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Great location and good rates for the 2 nights that we stayed. Staff was great and helpful. Closed to shops, cafe, and restaurants."
United States
Pang
The price is AU$233
includes taxes & fees
28 Sept - 29 Sept
Hadley Resort and Marina
Exterior

10. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (415 reviews)
"Great place to stay!"
United States
Virginia
The price is AU$323
includes taxes & fees
12 Oct - 13 Oct
Sands of Islamorada
Property grounds

11. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (81 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$747
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
Exterior

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is AU$1,715
includes taxes & fees
25 Sept - 26 Sept
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Terrace/patio

13. 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$1,715
includes taxes & fees
25 Sept - 26 Sept
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Exterior

14. 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$2,573
includes taxes & fees
25 Sept - 26 Sept
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior

15. 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$5,181
includes taxes & fees
18 Oct - 19 Oct
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm 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$2,793
includes taxes & fees
25 Sept - 26 Sept
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$2,777
includes taxes & fees
25 Sept - 26 Sept
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Exterior

18. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (457 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$264
includes taxes & fees
19 Oct - 20 Oct
Casa Morada
Exterior

19. Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is AU$3,257
includes taxes & fees
25 Sept - 26 Sept
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Exterior

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is AU$3,429
includes taxes & fees
25 Sept - 26 Sept
Charming Suite @Islamorada With Pool Access - Twilight 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

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

8/10 Good
"The hotel category and food quality should be better, given the price."
Juan 1-night trip
Posted 1 hour ago
Playa Largo Resort & Spa, Autograph Collection

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
11,578
Accommodation
2 Cabin Rentals
Lowest Price
AU$139
Highest Price
AU$747

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$139 to AU$747 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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