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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cabin Rentals in Upper Matecumbe Key and around

Best of Keys! Private Beach!
Beach

Best of Keys! Private Beach!

Best of Keys! Private Beach!
Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock
Enjoy stunning ocean views from the resort's thatched-roof structures, surrounded by palm trees and a sandy beach.

Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock

9.0 out of 10, Wonderful, (2)
"We loved staying here. We had 4 adults and 3 children with us so we rented both sides of the duplex. The house has everything you will need while visiting. One of the sides of the duplex was very musty when we arrived. We had to open up the windows to air it out the first night. The beach is gorgeous and there is sea grass in the water so that may deter some people. We enjoy snorkeling so the grass wasn’t an issue for us. When snorkeling in front of the house we saw a manatee, barracuda,...
Dog-Friendly, Oceanfront Duplex with Private Beach Access & Dock
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Great all around!"
Idalmis 1-night trip
Posted 19 hours ago
Cheeca Lodge & Spa

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 to 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.