Book Villas in Upper Matecumbe Key, FL

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Top Villas in Upper Matecumbe Key

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Free Cancellation

Reserve now, pay when you stay

$658 nightly

$740 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the playground and barbecue grills.

Pool

Hot Tub

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

Duck Key FL

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This villa features laundry facilities.

Washer

Dryer

Seas the Keys Getaway

Duck Key FL

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A gym is featured at this villa, along with laundry facilities.

Pool

Kitchen

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

Duck Key FL

$583 nightly

$647 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

This villa features laundry facilities.

Kitchen

Washer

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

Marathon FL

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This villa features laundry facilities.

Pool

Kitchen

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

Duck Key FL

$577 nightly

$641 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This villa features laundry facilities.

Kitchen

Washer

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

Duck Key FL

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This villa includes a garden and laundry facilities.

Kitchen

Washer

Waterfront House with Boat Dock

213 Aberdeen Ct Tavernier FL

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This villa features a picnic area, laundry facilities, and free self parking. Luggage storage and a virtual front desk are also provided.

Kitchen

Washer

Stunning Waterfront Two-Story Villa in Duck Key!

Duck Key FL

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This villa features laundry facilities.

Kitchen

Washer

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

Marathon FL

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A hot tub is featured at this villa, along with laundry facilities.

Hot Tub

Kitchen

4BR Key Largo Villa w/ Beach & Marriott Perks

Key Largo FL

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This villa featured laundry facilities and concierge services.

Pool

Kitchen

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Islamorada FL

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This villa features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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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.

Top hotels in Upper Matecumbe Key

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

$228 nightly

$257 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

9.2/10 Wonderful! (1,597 reviews)

Upper Matecumbe Key Villas essential information

Accommodation	95 Villas
Lowest Price	$200
Highest Price	$740
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!, DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl., 4BR Key Largo Villa w/ Beach & Marriott Perks, Serenity by the Sea!! Anglers Reef with Boat Slip Available!!