Compare Upper Matecumbe Key Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Upper Matecumbe Key

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
$569 nightly
The price is $640 total per night
$640 total
Aug 2 - Aug 3
Total with taxes and fees
Guests of The Islands of Islamorada have access to a marina, 2 outdoor pools, and a 24-hour gym. There's free parking if you drive. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this beach villa include free WiFi in public areas, a hot tub, and free use of bicycles.
Pool
Hot Tub
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA

Duck Key FL
$550 nightly
The price is $611 total per night
$611 total
Aug 24 - Aug 25
Total with taxes and fees
At this villa, guests have access to features like laundry facilities. This beach villa also has a garden.
Kitchen
Washer
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Duck Key FL
$553 nightly
The price is $614 total per night
$614 total
Aug 12 - Aug 13
Total with taxes and fees
At this villa, guests have access to features like laundry facilities.
Kitchen
Washer
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

Marathon FL
At this villa, guests have access to features like laundry facilities.
Pool
Kitchen
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

Marathon FL
Guests staying at this villa enjoy a hot tub and laundry facilities.
Hot Tub
Kitchen
Newly upgraded Key Largo Villa W/Boat Slip

Newly upgraded Key Largo Villa W/Boat Slip

Key Largo FL
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Keys Villa

Keys Villa

Islamorada FL
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Duck Key waterfront villa with private pool, kayak, SUP

Duck Key waterfront villa with private pool, kayak, SUP

Duck Key FL
This villa is a smoke-free villa.
Pool
Kitchen
Tropical bayfront villa with sandy beach

Tropical bayfront villa with sandy beach

Key Largo FL
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Upper Matecumbe Key
View all properties
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

    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82 Islamorada FL
    $202 nightly
    The price is $227 total per night from Aug 10 to Aug 11
    $227 total
    Aug 10 - Aug 11
    Total with taxes and fees
    9.2/10 Wonderful! (1,364 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy Islamorada FL
    $223 nightly
    The price is $251 total per night from Aug 10 to Aug 11
    $251 total
    Aug 10 - Aug 11
    Total with taxes and fees
    8.8/10 Excellent! (1,313 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy Islamorada FL
    $197 nightly
    The price is $221 total per night from Aug 3 to Aug 4
    $221 total
    Aug 3 - Aug 4
    Total with taxes and fees
    9.2/10 Wonderful! (1,771 reviews)

Luxury Villas

Book luxury villas in Upper Matecumbe Key
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Upper Matecumbe Key. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Upper Matecumbe Key, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Upper Matecumbe Key
You won’t have a problem finding your own space in Upper Matecumbe Key. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Upper Matecumbe Key on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Upper Matecumbe Key rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Upper Matecumbe Key Villas essential information

Accommodation
111 Villas
Lowest Price
$221
Highest Price
$640
Popular accommodation
The Islands of Islamorada, Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA, Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA, DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included, DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl., Newly upgraded Key Largo Villa W/Boat Slip, Keys Villa, Duck Key waterfront villa with private pool, kayak, SUP, Tropical bayfront villa with sandy beach

More to Explore