1319+ Luxury Vacation Rentals & Cabins in Upper Matecumbe Key |
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Upper Matecumbe Key Cabin Rentals

About Upper Matecumbe Key Vacation Rentals

There are more than 1319 incredible getaway rentals that are available in Upper Matecumbe Key. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Upper Matecumbe Key.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Upper Matecumbe Key, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Upper Matecumbe Key. Places to stay near Upper Matecumbe Key are 784.6 ft² on average, with prices averaging CA $1,031 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Upper Matecumbe Key. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Upper Matecumbe Key

Type Count
Vacation Homes 780
Villas 112
Holiday Apartments 103
Others 15
Cottages 8
Unique Vacation Rentals 6

Use these Quick Filters to Find a Vacation Rental in Upper Matecumbe Key

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Upper Matecumbe Key with Cabinns.ca.

Weather in Upper Matecumbe Key, FL

View the weather forecast for Upper Matecumbe Key before booking your Upper Matecumbe Key Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Upper Matecumbe Key Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Upper Matecumbe Key. Discover Top Attractions For Your Next Outdoor Adventure.


Bud n' Mary's Dive Center
Hurricane Monument
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
John Pennekamp Coral Reef State Park
Jimmy Johnson's Big Chill
Theater of the Sea
Dolphins Plus Bayside
Dolphin Cove
Founders Park
Anne's Beach
Caribbean Club Bar
Dolphins Plus
Harry Harris Park
Bluefin Rock Harbor Marina
Florida Keys Dive Center
Harry Harris Park
Florida Keys Flats Fishing
Islamorada County Park

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Islamorada 880 Properties
History of Diving Museum 811 Properties
Matecumbe United Methodist Church 647 Properties
Florida Keys Brewing Co. 632 Properties
Hurricane Monument 630 Properties
Coral Cove 542 Properties
Bud n' Mary's Dive Center 522 Properties

Complexes around Upper Matecumbe Key, FL


Executive Bay Club Islamorada 12 Properties
Anglers Reef Islamorada 7 Properties
Summer Sea Islamorada 6 Properties
Anglers Way Islamorada 4 Properties
Futura Yacht Club 2 Properties
Maison Matecumbe Islamorada 2 Properties
Bay Harbour Islamorada 1 Properties
Futura Yacht Club Islamorada 1 Properties

Frequently Asked Questions About Upper Matecumbe Key?

What are the top cabins, lake houses & summer homes in Upper Matecumbe Key?

We provide an array of great vacation destinations in Upper Matecumbe Key. If you are looking to stay in or around the Upper Matecumbe Key area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Upper Matecumbe Key:

How many cabin rentals and resorts have private pools in Upper Matecumbe Key?

We have 186 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Upper Matecumbe Key. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Upper Matecumbe Key is best for families?

Searching for a family-friendly cabin in Upper Matecumbe Key? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Upper Matecumbe Key?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 1319 in the Upper Matecumbe Key area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Upper Matecumbe Key.

Nearby Neighborhood (1) 
Neighborhood Property Count
Coral Cove Rental Cabins and Private Getaways in Florida 542

People Also Ask

There are 125 hotels in Upper Matecumbe Key 57 resorts, and 995 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Upper Matecumbe Key