Compare Upper Matecumbe Key Resorts

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Hotel Options in Upper Matecumbe Key

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy Islamorada FL
    $213 nightly
    The price is $240 total per night from Jan 14 to Jan 15
    $240 total
    Jan 14 - Jan 15, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (1,598 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy Islamorada FL
    $271 nightly
    The price is $305 total per night from Jan 8 to Jan 9
    $305 total
    Jan 8 - Jan 9, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,268 reviews)
    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82 Islamorada FL
    $504 nightly
    The price is $568 total per night from Jan 3 to Jan 4
    $568 total
    Jan 3 - Jan 4, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (1,269 reviews)

Resort Hotels

Resort hotels in Upper Matecumbe Key
Find your next great getaway when you book at a resort hotel in Upper Matecumbe Key. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Upper Matecumbe Key at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Upper Matecumbe Key is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Upper Matecumbe Key
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Upper Matecumbe Key resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Upper Matecumbe Key Resorts essential information

Accommodation
Resorts
Lowest Price
$240
Highest Price
$568
Popular accommodation
Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa

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