1319+ Vacation Rentals & Holiday Homes in Upper Matecumbe Key |
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Upper Matecumbe Key Accommodations - Hotels & Rentals

About Upper Matecumbe Key Vacation Rentals

Discover More than 1319 Incredible Getaway Rentals Available in Upper Matecumbe Key. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Upper Matecumbe Key.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Upper Matecumbe Key, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Upper Matecumbe Key. The Average Size of Places to Stay Near Upper Matecumbe Key is 784.6 ft², with Prices Averaging US $738 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Upper Matecumbe Key. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Upper Matecumbe Key

Type Count
Vacation Homes 780
Villas 112
Holiday Apartments 103
Cottages 8

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Upper Matecumbe Key with Online Reservations.

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 KeyGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Upper Matecumbe KeyGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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 Hotels & Vacation Rentals in these Cities and 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

Frequently Asked Questions About Upper Matecumbe Key?

What are the top hotels, lake houses & vacation rentals 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 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 Hotels & Vacation Rentals have private pools in Upper Matecumbe Key?

We have 185 Hotels & Vacation 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 hotel, lake house, or vacation rental in Upper Matecumbe Key is best for families?

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

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

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ 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, Online Reservations™ 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 Vacation Rentals in Florida 542

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