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Our top choices for Islamorada villas

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is NZ$1,278
includes taxes & fees
5 Jan - 6 Jan 2026
The Islands of Islamorada
2.0 star property
Waterfront Luxe Pool, Hot Tub, Theater, Gamesandmore
8.6 out of 10, Excellent, (25)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is NZ$1,037
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
9.2 out of 10, Wonderful, (30)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is NZ$1,082
includes taxes & fees
13 Jan - 14 Jan 2026
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
10.0 out of 10, Exceptional, (4)
"Everything about the stay was nice. "
United States
Mario S.
The price is NZ$1,101
includes taxes & fees
8 Jan - 9 Jan 2026
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
10.0 out of 10, Exceptional, (1)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is NZ$1,255
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
The price is NZ$1,990
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
10.0 out of 10, Exceptional, (13)
"We enjoyed our stay here! It was perfect for a family of 4!"
United States
Amy S.
The price is NZ$1,286
includes taxes & fees
4 Jan - 5 Jan 2026
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
9.6 out of 10, Exceptional, (57)
"Great location for our family.We love the Keys. Beautiful sunsets from balconies."
United States
Debbie A.
The price is NZ$1,093
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
The price is NZ$1,884
includes taxes & fees
14 Jan - 15 Jan 2026
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
9.2 out of 10, Wonderful, (18)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
The price is NZ$1,105
includes taxes & fees
11 Jan - 12 Jan 2026
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
9.0 out of 10, Wonderful, (8)
"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
10.0 out of 10, Exceptional, (1)
"The host was extremely communicative and welcoming. What ever we needed he provided"
United States
Amy G.
The price is NZ$1,094
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
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 Islamorada Hotel Reviews

Find out more about Islamorada

Islamorada Villas information

Number of reviews
215
Accommodation
64 Villas
Lowest Price
NZ$1,037
Highest Price
NZ$1,990

Frequently asked questions

How much do villas in Islamorada cost?
Prices for villas in Islamorada range between NZ$1,037 and NZ$1,990 per night. Whatever your budget, you'll find a place that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Islamorada?
Choose from 64 villas in Islamorada. Whether you're taking a trip with the family or planning a getaway with some friends, Expedia can help you find the perfect space for your whole crew.
What is there to do near my villa in Islamorada?
Whatever you're into, Islamorada has tons of things to keep you entertained. Florida Keys Brewing Co., History of Diving Museum and Bud n' Mary's Dive Centre are on most visitors' agendas. Don't head home without exploring Windley Key Fossil Reef Geological State Park, Theatre of the Sea and Anne's Beach either. With Expedia's hotel deals in Islamorada, you'll be able to discover more wonderful attractions like these with the cash you save.

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