A beach with white lounge chairs, a covered pavilion, and palm trees.

Search Islamorada Villa Rentals from CA $712

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Check prices for these dates

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

Our top choices for Islamorada 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 CA $410
CA $863 total
includes taxes & fees
Oct 18 - Oct 19
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
The price is CA $4,301
CA $6,951 total
includes taxes & fees
Nov 8 - Nov 9
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

3. 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 CA $373
CA $814 total
includes taxes & fees
Oct 17 - Oct 18
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
A resort with a central pool, multiple buildings, and a view of the ocean.

4. 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 CA $708
CA $1,290 total
includes taxes & fees
Oct 17 - Oct 18
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
A resort with a pool, palm trees, and a view of the ocean.

5. 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.
The price is CA $2,370
CA $4,376 total
includes taxes & fees
Nov 8 - Nov 9
PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
A coastal resort with multiple bungalow-style buildings, a marina, and a large body of water.

6. 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.
The price is CA $396
CA $1,176 total
includes taxes & fees
Oct 26 - Oct 27
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A living room with a view of the sea, a ceiling fan, a TV, and a dining area with outdoor seating.

7. 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
The price is CA $255
CA $728 total
includes taxes & fees
Oct 20 - Oct 21
Villa 5034 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.

8. 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.
The price is CA $309
CA $796 total
includes taxes & fees
Oct 18 - Oct 19
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
A covered balcony with white railings, a white wicker chair, and a small table.

9. 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.
The price is CA $578
CA $1,408 total
includes taxes & fees
Oct 19 - Oct 20
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
A deck with outdoor seating, overlooking a marina and a body of water.

10. 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 CA $268
CA $745 total
includes taxes & fees
Oct 19 - Oct 20
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
A covered outdoor patio with a table and chairs, a ceiling fan, and a view of trees and a white building.

11. 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.
The price is CA $241
CA $712 total
includes taxes & fees
Oct 19 - Oct 20
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
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.
The price is CA $255
CA $730 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $241
CA $712 total
includes taxes & fees
Oct 19 - Oct 20
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great location"
Dianne 5-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada Villas information

Number of reviews
564
Accommodation
82 Villas
Lowest Price
CA $712
Highest Price
CA $6,951

Frequently asked questions

How much do villas in Islamorada cost?
Prices for villas in Islamorada range between CA $712 and CA $6,951 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 82 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.
Are there any family-friendly villas in Islamorada?
If you're on your way to Islamorada and searching for a family-friendly villa, you can't pass up Anglers Reef Villa 1. This 3.5-star stay features amenities like a barbecue grill and an oven. After checking in and chilling together in your cozy digs, it's time to hit the road and discover some of the local sights. Theatre of the Sea and Anne's Beach are just two family-friendly attractions in Islamorada.
Why book your villa in Islamorada with Expedia?
Booking a villa in Islamorada is as simple as entering your travel dates and picking an option that has what you need. Looking for something low cost or luxurious, or a stay that also features a kitchen? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Islamorada?
Expedia can help you track down cheap villas in Islamorada. Simply use the filter tool to select star rating, amenities and budget to refine your search and find a great place to stay in a few quick clicks.
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 Center are on most visitors' agendas. Don't head home without exploring Windley Key Fossil Reef Geological State Park, Theater 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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