A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Upper Matecumbe Key villas

A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

1. Key Largo Kawama villa K1, 3/3

Key Largo Kawama villa K1, 3/3
Key Largo
9.8 out of 10, Exceptional, (191 reviews)
"This was a great location, very clean and well equipped. Great stay!"
United States
Diana
The price is AU$799
includes taxes & fees
15 Oct - 16 Oct
Key Largo Kawama villa K1, 3/3
A balcony with a view of the beach and ocean, equipped with ceiling fans, outdoor furniture, and a railing.

2. Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key

Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
Matecumbe
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
Exterior Front

3. Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (15 reviews)
"Nice location "
United States
Gina W.
Seas the Keys Getaway with plunge pool/spa
A living room with a view of the sea, a ceiling fan, a TV, and a dining area with outdoor seating.

4. Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.8 out of 10, Exceptional, (8 reviews)
"Great Location! The house was beautiful and clean We had a great time!"
United States
Andres
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

5. Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (142 reviews)
"We couldn’t have asked for more! And we had the saltwater lagoon and the pool and bicycles and the ocean all right outside our door. What a beautiful place to stay!"
United States
Kara L.
The price is AU$817
includes taxes & fees
22 Oct - 23 Oct
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
A deck with outdoor seating, overlooking a marina and a body of water.

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

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (23 reviews)
"Awesome place to stay"
United States
Takuma F.
The price is AU$734
includes taxes & fees
15 Oct - 16 Oct
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor seating area with a table and chairs, overlooking a body of water and a beach.

7. Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
A resort with a central pool, multiple buildings, and a view of the ocean.

8. Beautiful Oceanside Mariner`s 3 Bedroom Townhome

Beautiful Oceanside Mariner`s 3 Bedroom Townhome
Rock Harbor
10.0 out of 10, Exceptional, (108 reviews)
"Amazing place!!"
United States
Sonal G.
The price is AU$1,261
includes taxes & fees
15 Oct - 16 Oct
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
A coastal resort with multiple bungalow-style buildings, a marina, and a large body of water.

9. Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
Marathon
9.6 out of 10, Exceptional, (5 reviews)
"Hawks Cay is a really beautiful spot. Frank’s place is nice, clean and convenient to Marathon "
United States
Morgan W.
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

10. Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered balcony with white railings, a white wicker chair, and a small table.

11. Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Duck Key
10.0 out of 10, Exceptional, (5 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
A covered outdoor area with a round table and chairs, a white railing, and a view of the ocean.

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

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (64 reviews)
"Excellent place,"
United States
MONICA A.
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor deck with a table and chairs, overlooking a body of water and a grassy area.

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

Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.8 out of 10, Excellent, (6 reviews)
"The property was as described in the VRBO site. The view was very nice. I would stay here again, when the opportunity arises."
United States
Paul E.
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
A resort with a pool, palm trees, and a view of the ocean.

14. PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key

PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
Matecumbe
10.0 out of 10, Exceptional, (1 review)
"Very nice house. Easy to communicate with host. Views just as pictured, great. Dock in front of house is too shallow for a boat but host can provide boat slip very within walking distance 30’ boat max."
United States
Jason B.
PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
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.
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Estelar propiedad muy acogedora de día y de noche."
Juan 1-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Villas information

Number of reviews
579
Accommodation
120 Villas
Lowest Price
AU$734
Highest Price
AU$1,261

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