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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Upper Matecumbe Key cabin rentals

Reception

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,450 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is ￥21,739
￥35,930 total
includes taxes & fees
Sep 24 - Sep 25
Cheeca Lodge & Spa
Water view

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,782 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is ￥22,512
￥34,150 total
includes taxes & fees
Sep 28 - Sep 29
Chesapeake Beach Resort
Exterior

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,123 reviews)
"Great palace to stay at a reasonable price"
United States
John
The price is ￥30,360
￥44,744 total
includes taxes & fees
Sep 30 - Oct 1
Islander Resort
Aerial view

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,317 reviews)
"amazing clean stay."
United States
MICHAEL
The price is ￥22,553
￥36,845 total
includes taxes & fees
Sep 24 - Sep 25
Amara Cay Resort
Dock

5. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (464 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is ￥38,777
￥54,241 total
includes taxes & fees
Sep 23 - Sep 24
Bayside Villas by Islander Resort
Exterior

6. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,005 reviews)
"The room was very nice and neat !"
United States
Leslie
The price is ￥10,077
￥15,750 total
includes taxes & fees
Oct 5 - Oct 6
La Jolla Resort
Exterior

7. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
The price is ￥18,405
￥29,379 total
includes taxes & fees
Sep 24 - Sep 25
Pines & Palms Resort
Property grounds

8. 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 ￥64,948
￥83,014 total
includes taxes & fees
Oct 1 - Oct 2
The Islands of Islamorada
Exterior

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
"Great place"
United States
weder
The price is ￥18,586
￥26,042 total
includes taxes & fees
Sep 28 - Sep 29
Hadley Resort and Marina
Exterior

10. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
United States
Dionisio
The price is ￥10,990
￥14,872 total
includes taxes & fees
Sep 29 - Sep 30
Breezy Palms Resort
Exterior

11. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
United States
Nicolas
The price is ￥30,121
￥36,004 total
includes taxes & fees
Oct 1 - Oct 2
Sands of Islamorada
Exterior

12. 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 ￥24,635
￥29,485 total
includes taxes & fees
Oct 19 - Oct 20
Casa Morada
View from property

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (276 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
The price is ￥31,250
￥46,630 total
includes taxes & fees
Sep 28 - Sep 29
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Exterior

14. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
The price is ￥17,249
￥24,538 total
includes taxes & fees
Sep 23 - Sep 24
Fisher Inn Resort & Marina
Exterior

15. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (293 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
The price is ￥22,674
￥25,508 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
Premium bedding, iron/ironing board, WiFi (free), individually decorated

16. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Great location,"
United States
Marianela
The price is ￥18,828
￥26,688 total
includes taxes & fees
Sep 24 - Sep 25
Drop Anchor
Classic Room, Patio, Garden View | WiFi (free)

17. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (32 reviews)
"Very friendly staff"
United States
Maria
The price is ￥29,227
￥32,879 total
includes taxes & fees
Sep 30 - Oct 1
The Ocean View Inn & Pub
Front of property

18. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,021 reviews)
"Great place to stay for the night."
United States
Terry
The price is ￥21,262
￥23,920 total
includes taxes & fees
Sep 27 - Sep 28
Creekside Inn
Private beach, white sand

19. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (163 reviews)
"Worth the money."
United States
paul
The price is ￥19,484
￥21,920 total
includes taxes & fees
Sep 24 - Sep 25
Matecumbe Resort
Exterior

20. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (557 reviews)
"Beautiful place hidden in Tavenier Great staff and the best sunset in the keys"
United States
ED
The price is ￥29,509
￥39,376 total
includes taxes & fees
Sep 24 - Sep 25
Coconut Palm Inn
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

8/10 Good
"Very quiet and peaceful stay. Amazing water and beach views from the balcony."
Michelle 4-night trip
Posted 5 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
12,316
Accommodation
2 Cabin Rentals
Lowest Price
￥14,872
Highest Price
￥83,014

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 ￥14,872 to ￥83,014 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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