Search Cabins in Upper Matecumbe Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Cabin Rentals in Upper Matecumbe Key

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"This was our first time here. The property is beautiful! The kids LOVED playing at the main pool, lagoon & other pool w/ pirate ship splash pad. Our only complaint is the water in all these areas is very warm except the pool by the pirate ship. Maybe when they build the new water slide area they will include a system that keeps the water cool & refreshing. Food & drinks were delicious but also expensive. We mostly ordered from the main pool tiki bar/grill. Jacob & Tomas from Turkey were so friendly & provided excellent service! We tried Salt & Ash for a nice fancy dinner & were not disappointed. Breakfast in the cafe always had a long line so be prepared. They accidentally had us listed as taking our food to go even though we did not request that. They gave us a number to place on our table but the food never came out & sat at the counter forever until we finally inquired as to the wait. We assumed it was taking long bc they were so busy. So that was a bit disappointing. We had the family oasis room w/ bunk beds which was perfect for us. There isn’t a view (looks out to the back of a building), but that didn’t bother us since we were barely in our room. Beds were comfortable, the AC was cold & the shower hot. We spent 3 nights there & didn’t leave the property except for one time to have dinner at Lazy Days in Islamorada which was so good. Though there are some areas that can be improved, overall we had a wonderful trip & look forward to coming back."
Siobhan 3-night trip
Posted 3 days ago
Hawks Cay Resort

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.