Compare Upper Matecumbe Key Condo Rentals

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Featured Condo Rentals in Upper Matecumbe Key

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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.

Hotel Options in Upper Matecumbe Key

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy Islamorada FL
    $211 nightly
    The price is $238 total per night from Jan 6 to Jan 7
    $238 total
    Jan 6 - Jan 7, 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
    $319 nightly
    The price is $359 total per night from Dec 19 to Dec 20
    $359 total
    Dec 19 - Dec 20
    Total with taxes and fees
    9.2/10 Wonderful! (1,269 reviews)

Luxury Condos

Find luxury condos in Upper Matecumbe Key
Get your vacation off to a fabulous start by booking a luxury condo in Upper Matecumbe Key. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a Upper Matecumbe Key condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.  

Exploring Upper Matecumbe Key will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

Upper Matecumbe Key Condo Rentals essential information

Accommodation
390 Condo Rentals
Lowest Price
$238
Highest Price
$359
Popular accommodation
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball, Ohana Cay 4 bed & 4 bath Unit 906 @Mariners Club - Sleeps 10!!, Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico., Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!, Keys Deal w/Cafe & Pool Bar! Up to 20% Off Beachfront 1BD Sleeps 4., Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball, Oceanfront Community, Luxury,Beach,Pools, TOP AMENITIES & VALUE in FLORIDA KEYS, Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!, Condo with Pool and Beach Access

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