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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec
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, (1,761 reviews)
"Beautiful resort! Very tropical vibes! I would definitely stay here again!"
United States
Alisha
The price is €194
includes taxes & fees
25 Aug - 26 Aug
Chesapeake Beach Resort
Reception

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,417 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
The price is €206
includes taxes & fees
2 Sept - 3 Sept
Cheeca Lodge & Spa
Exterior

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location and great staff"
United States
adrian
The price is €139
includes taxes & fees
27 Aug - 28 Aug
La Jolla Resort
Exterior

4. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,108 reviews)
"Staff and resort were amazing!"
United States
Chris
The price is €273
includes taxes & fees
31 Aug - 1 Sept
Islander Resort
Exterior

5. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"I had an excellent stay at the resort. and look forward to returning!"
United States
Isabel
The price is €216
includes taxes & fees
30 Aug - 31 Aug
Pines & Palms Resort
Exterior

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (729 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is €112
includes taxes & fees
1 Sept - 2 Sept
Breezy Palms Resort
Aerial view

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,294 reviews)
"Best place to stay !!"
United States
David A
The price is €224
includes taxes & fees
24 Aug - 25 Aug
Amara Cay Resort
Exterior

8. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,013 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is €134
includes taxes & fees
15 Sept - 16 Sept
Hadley Resort and Marina
Dock

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (457 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is €284
includes taxes & fees
31 Aug - 1 Sept
Bayside Villas by Islander Resort
Suite, 1 King Bed with Sofa bed, Ocean View | Exterior

10. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,011 reviews)
"Great place to stay!"
United States
Brianne
The price is €211
includes taxes & fees
25 Aug - 26 Aug
La Siesta Resort & Villas
Property grounds

11. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (80 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 €400
includes taxes & fees
31 Aug - 1 Sept
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 €205
includes taxes & fees
17 Sept - 18 Sept
Sands of Islamorada
Exterior

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is €1,758
includes taxes & fees
4 Sept - 5 Sept
Terrace & Florida Bay View Suite @Islamorada - Shangri La 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 €1,096
includes taxes & fees
4 Sept - 5 Sept
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
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 €3,314
includes taxes & fees
28 Aug - 29 Aug
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Exterior

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is €1,086
includes taxes & fees
4 Sept - 5 Sept
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo 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 €1,786
includes taxes & fees
28 Aug - 29 Aug
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Exterior

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is €1,657
includes taxes & fees
28 Aug - 29 Aug
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior

19. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (451 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 €169
includes taxes & fees
31 Aug - 1 Sept
Casa Morada
Exterior

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is €2,171
includes taxes & fees
4 Sept - 5 Sept
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Amazing breakfast, clean room and very friendly staff."
Oleksandr 5-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
11,381
Accommodation
2 Cabin Rentals
Lowest Price
€93
Highest Price
€400

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 €93 to €400 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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