Compare Upper Matecumbe Key Villas

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Featured Villas in Upper Matecumbe Key

Free Cancellation

Reserve now, pay when you stay

$948 nightly

$1,067 total

Feb 26 - Feb 27

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, wedding services, and a garden.

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

$695 nightly

$772 total

Mar 10 - Mar 11

Total with taxes and fees

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

$639 nightly

$639 total

Mar 14 - Mar 15

Total with taxes and fees

This villa features a gym and laundry facilities.

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

$730 nightly

$811 total

Feb 23 - Feb 24

Total with taxes and fees

At this villa, guests have access to features like laundry facilities.

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

At this villa, guests have access to features like laundry facilities.

Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA

$736 nightly

$817 total

Feb 18 - Feb 19

Total with taxes and fees

At this villa, guests have access to features like laundry facilities.

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.

At this villa, guests have access to a children's pool, laundry facilities, and a picnic area. Free parking is included with your stay. A multilingual staff is on hand to help with luggage storage, and offer sightseeing advice.

Stunning Waterfront Two-Story Villa in Duck Key!

At this villa, guests have access to features like laundry facilities.

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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

83409 Overseas Hwy Islamorada FL

$463 nightly

$521 total

Mar 2 - Mar 3

Total with taxes and fees

9.2/10 Wonderful! (1,672 reviews)

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$414 nightly

$466 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (1,301 reviews)

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

$423 nightly

$476 total

Feb 25 - Feb 26

Total with taxes and fees

8.8/10 Excellent! (1,265 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	95 Villas
Lowest Price	$466
Highest Price	$1,067
Popular accommodation	The Islands of Islamorada, Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg, Seas the Keys Getaway, Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA, DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included, Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA, Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer, Waterfront House with Boat Dock, Stunning Waterfront Two-Story Villa in Duck Key!