1463+ Private Villas and Holiday Rentals in Upper Matecumbe Key |
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Upper Matecumbe Key Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Upper Matecumbe Key

Discover more than 1463 vacation rentals available in Upper Matecumbe Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upper Matecumbe Key.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upper Matecumbe Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upper Matecumbe Key. On average, places to stay near Upper Matecumbe Key offer 969.56 ft², with nightly prices averaging $745.

With Casai, finding and comparing holiday rentals in Upper Matecumbe Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Upper Matecumbe Key

Type Count
Vacation Homes 932
Villas 129
Holiday Apartments 128
Cottages 11

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Upper Matecumbe Key.

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

Top Attractions Around Upper Matecumbe Key, FL

Casai offers a large selection of top attractions around Upper Matecumbe Key . Research things to do on your vacation before you visit Upper Matecumbe Key.


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

Other Places to Stay in Upper Matecumbe Key, FL


Islamorada 976 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

Frequently Asked Questions About Upper Matecumbe Key?

What are the top holiday rentals in Upper Matecumbe Key?

With numerous options available in Upper Matecumbe Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upper Matecumbe Key:

How many holiday rentals have private pools in Upper Matecumbe Key?

Discover a selection of holiday rentals with private pools near Upper Matecumbe Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Upper Matecumbe Key are best for families?

If you're searching for a family-friendly holiday home in Upper Matecumbe Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upper Matecumbe Key:

How many Casai.com holiday rentals are available in Upper Matecumbe Key?

As of 2025, Casai boasts over 1463 properties listed in the Upper Matecumbe Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upper Matecumbe Key.

Nearby Neighborhood (1) 
Neighborhood Property Count
Coral Cove Vacation Rentals in Florida 542

People Also Ask

There are 1463 Upper Matecumbe Key, FL Holiday Rentals

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