Compare Upper Matecumbe Key Villas

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Featured Villas in Upper Matecumbe Key

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
$599 nightly
The price is $674 total per night
$674 total
Oct 21 - Oct 22
Total with taxes and fees
Guests staying at The Islands of Islamorada enjoy access to 2 outdoor pools, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach villa include a hot tub, barbecue grills, and a garden.
Pool
Hot Tub
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

At this villa, guests have access to features like laundry facilities. This beach villa also has a garden.
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

At this villa, guests have access to features like laundry facilities.
Pool
Kitchen
Seas the Keys Getaway

Seas the Keys Getaway

$408 nightly
The price is $455 total per night
$455 total
Oct 27 - Oct 28
Total with taxes and fees
This villa features a gym and laundry facilities.
Pool
Kitchen
Our place overlooks the Atlantic. Our marina is less than 50 ft from our patio

Our place overlooks the Atlantic. Our marina is less than 50 ft from our patio

Guests of this villa enjoy features like an outdoor pool, a gym, and laundry facilities. This family-friendly villa also has a garden.
Pool
Kitchen
Charming 3-Bedroom Villa Centrally Located in the Florida Keys

Charming 3-Bedroom Villa Centrally Located in the Florida Keys

At this villa, guests have access to an outdoor pool, laundry facilities, and a garden.
Pool
Kitchen
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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

$493 nightly
The price is $550 total per night
$550 total
Oct 21 - Oct 22
Total with taxes and fees
At this villa, guests have access to features like laundry facilities.
Kitchen
Washer
Crystal Waters - 2/2.5 Villa

Crystal Waters - 2/2.5 Villa

At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Kitchen
Washer
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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

    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    $199 nightly
    The price is $224 total per night from Oct 26 to Oct 27
    $224 total
    Oct 26 - Oct 27
    Total with taxes and fees
    9/10 Wonderful! (1,232 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    $208 nightly
    The price is $234 total per night from Oct 26 to Oct 27
    $234 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8.8/10 Excellent! (1,259 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    $173 nightly
    The price is $194 total per night from Oct 22 to Oct 23
    $194 total
    Oct 22 - Oct 23
    Total with taxes and fees
    9.2/10 Wonderful! (1,549 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
87 Villas
Lowest Price
$194
Highest Price
$674
Popular accommodation
The Islands of Islamorada, Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer, DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included, Seas the Keys Getaway, Our place overlooks the Atlantic. Our marina is less than 50 ft from our patio, Charming 3-Bedroom Villa Centrally Located in the Florida Keys, Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!, Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA, Crystal Waters - 2/2.5 Villa

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