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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Featured Cabin Rentals in Upper Matecumbe Key

Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1216)
"This is a beautiful resort in a perfect location in the Keys. They have lots of amenities right on the beach. We would definitely stay here again! "
The price is AU$730
includes taxes & fees
4 Feb - 5 Feb
Amara Cay Resort
Chesapeake Beach Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1393)
"Went to a weeding in Islamorada and the option of the hotel was ideal "
The price is AU$603
includes taxes & fees
3 Feb - 4 Feb
Chesapeake Beach Resort
Cheeca Lodge & Spa
Private beach, sun-loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1033)
"The resort was beautiful, clean, and well managed. We had a beautiful room with stylish furniture. Fun things to do at the resort (fish, swim, pitch and putt golf), within walking distance to other fun restaurants and stores. "
The price is AU$830
includes taxes & fees
6 Feb - 7 Feb
Cheeca Lodge & Spa
La Siesta Resort & Villas
Outdoor pool, pool loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1004)
"It’s very relaxing with tropical feel. It feels like a private quiet island. Noel at the tiki bar was great. "
The price is AU$648
includes taxes & fees
5 Feb - 6 Feb
La Siesta Resort & Villas
Islander Resort
Exterior

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1009)
"Beautiful property and very accommodating. "
The price is AU$693
includes taxes & fees
9 Feb - 10 Feb
Islander Resort
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
8.0 out of 10, Very good, (1002)
"When we arrived our room was ready and the staff was very friendley."
The price is AU$433
includes taxes & fees
3 Feb - 4 Feb
Hadley Resort and Marina
Sunset Inn
Outdoor pool, free pool cabanas

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1003)
"Outstanding. Friendly staff. Simple, spacious, immaculately clean room. Grounds were well kept and the pool warm and deck area inviting. Absolutely will be back."
The price is AU$424
includes taxes & fees
3 Feb - 4 Feb
Sunset Inn
La Jolla Resort
View from property

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Friendly and helpful staff. Nice room"
The price is AU$405
includes taxes & fees
3 Feb - 4 Feb
La Jolla Resort
The Caribbean Resort
Exterior

The Caribbean Resort

3.5 star property
10.0 out of 10, Exceptional, (150)
"Staff is always great. Rooms are beautiful & clean. Feels like I am at home"
The Caribbean Resort
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, pool loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (358)
"We booked here because of the full kitchen plus living areas; the kitchen was pretty sparse regarding cookware/appliances, but the front desk bent over backwards to get us the missing items we requested. One of the selling points was access to their resort property, just up the street. However, that property was almost deserted due to a lot of construction work. The resort pool was closed (the Bayside Villas pool was open). Overall this was a pleasant stay for us."
The price is AU$652
includes taxes & fees
9 Feb - 10 Feb
Islander Bayside Villas and Boatslips
Casa Morada
Outdoor pool, pool umbrellas, pool loungers

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (378)
"Stayed overnight while attending a wedding on Islamorada. Room was comfortable and the property was beautiful! Wish we were able to stay for more than one night. Was pleasantly surprised to learn of the morning yoga class on Sunday mornings! Felt great to stretch and practice mindfulness. Will definitely stay at Casa Morada again in the future!"
The price is AU$662
includes taxes & fees
3 Feb - 4 Feb
Casa Morada
Sands of Islamorada
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (355)
"Loved the location of our room-we could easily get coffee and head out to sit and watch the sunrise. Ice machine broken so that was a bummer but the staff was phenomenal especially when allowing us to check in early."
The price is AU$487
includes taxes & fees
9 Feb - 10 Feb
Sands of Islamorada
Pines & Palms Resort
Poolside bar

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (975)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
The price is AU$593
includes taxes & fees
3 Feb - 4 Feb
Pines & Palms Resort
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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Other property types in Upper Matecumbe Key

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"nice warm pool, nice ocean views."
The price is AU$348
includes taxes & fees
13 Feb - 14 Feb
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (47)
"Beautiful property with great staff! "
The price is AU$1,164
includes taxes & fees
2 Mar - 3 Mar
The Islands of Islamorada
Key Largo Cottages
Beach/ocean view

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is AU$732
includes taxes & fees
6 Feb - 7 Feb
Key Largo Cottages
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.

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.
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.