Search Cabins in Upper Matecumbe Key

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Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
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Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Cabin Rentals in Upper Matecumbe Key

We don't have any properties that match your exact search

Recommended hotels in Upper Matecumbe Key

Sunset Inn
Outdoor pool, free cabanas

Sunset Inn

3.0 star property
9.4 out of 10, Exceptional, (1002)
"Favorite place to stay in Islamorda "
The price is ￥20,880
￥25,132 total
includes taxes & fees
Jun 25 - Jun 26
Sunset Inn
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1000)
"Front desk had everything ready for me and it was quick and easy check in."
The price is ￥16,619
￥23,457 total
includes taxes & fees
Jun 26 - Jun 27
Hadley Resort and Marina
La Jolla Resort
View from property

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful waterfront hotel. Large rooms and great area. "
La Jolla Resort
La Siesta Resort & Villas
Outdoor pool, sun loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1005)
"great place"
The price is ￥23,550
￥36,179 total
includes taxes & fees
Jul 10 - Jul 11
La Siesta Resort & Villas
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1116)
"This is a beautiful resort and the staff is very friendly and competent."
The price is ￥24,100
￥36,961 total
includes taxes & fees
Jul 6 - Jul 7
Cheeca Lodge & Spa
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
Breezy Palms Resort
Islander Resort
Exterior

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1008)
"We loved our stay! Room was clean, comfortable; staff was friendly and very helpful. We really like the feeling of being"
The price is ￥31,009
￥44,746 total
includes taxes & fees
Jul 6 - Jul 7
Islander Resort
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1475)
"This was a great place to stay. "
Chesapeake Beach Resort
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1222)
"Very nice place"
The price is ￥26,154
￥39,109 total
includes taxes & fees
Jul 6 - Jul 7
Amara Cay Resort
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (999)
"Great quiet spot!"
Pines & Palms Resort
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (367)
"Had another amazing stay in a gorgeous waterfront unit! The sunset was breathtaking! Beds super comfy. Love this place"
The price is ￥37,207
￥51,706 total
includes taxes & fees
Jun 25 - Jun 26
Islander Bayside Villas and Boatslips
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, (382)
"Rooms updated and modern"
The price is ￥23,637
￥31,516 total
includes taxes & fees
Jun 26 - Jun 27
Sands of Islamorada
Casa Morada
Outdoor pool, pool umbrellas, sun loungers

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (399)
"Phenomenal staff, property and amenities! We will recommend to all of our friends and will definitely go back! Thank you for a wonderful stay, Casa Morada!"
Casa Morada
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ￥74,414
￥91,760 total
includes taxes & fees
Jul 11 - Jul 12
The Islands of Islamorada
Hidden Gem Islamorada | 1st Floor
Pool

Hidden Gem Islamorada | 1st Floor

10.0 out of 10, Exceptional, (41)
"Perfect location in islamorada. Definitely recommend and will stay there again. "
The price is ￥38,228
￥81,385 total
includes taxes & fees
Jul 7 - Jul 8
Hidden Gem Islamorada | 1st Floor
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (68)
"Great tiny house, enjoyed our stay"
The price is ￥20,801
￥57,963 total
includes taxes & fees
Jun 29 - Jun 30
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Hampton Inn Key Largo Manatee Bay
Room, 1 King Bed, Bay View | Beach/ocean view

Hampton Inn Key Largo Manatee Bay

2.5 star property
8.8 out of 10, Excellent, (1011)
"Stayed at this hotel many times now Great hotel in a great location for discovering the beautiful Florida Keys "
The price is ￥17,855
￥20,087 total
includes taxes & fees
Jun 30 - Jul 1
Hampton Inn Key Largo Manatee Bay
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (55)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is ￥23,480
￥62,000 total
includes taxes & fees
Jun 30 - Jul 1
Waterfront Tiny House w Pool, Beach, and Boat Dock
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (112)
"Best sunrise site."
The price is ￥32,620
￥73,303 total
includes taxes & fees
Jul 15 - Jul 16
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Waterfront Pool, Beach, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

9.8 out of 10, Exceptional, (75)
"Loved our stay!"
The price is ￥27,735
￥66,639 total
includes taxes & fees
Jun 29 - Jun 30
Waterfront Pool, Beach, Dock, Kayaks, Paddleboards
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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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.