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

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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 $364
CA $795 total
includes taxes & fees
Sep 13 - Sep 14
Key Largo Kawama villa K1, 3/3
A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

2. 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, (141 reviews)
"Had fun villa was in good condition."
United States
Michelle S.
The price is CA $386
CA $823 total
includes taxes & fees
Sep 13 - Sep 14
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
A balcony with a view of the beach and ocean, equipped with ceiling fans, outdoor furniture, and a railing.

3. 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 $2,557
CA $4,783 total
includes taxes & fees
Sep 14 - Sep 15
Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key
A coastal residential area with houses, a marina, and a clear view of the ocean.

4. Waterfront Luxe Pool, Hot Tub, Theater, Gamesandmore

Waterfront Luxe Pool, Hot Tub, Theater, Gamesandmore
Buccaneer Point
3.0 out of 10, (2 reviews)
"Canceled at 10pm the night before we were to arrive. Had to scramble to get hotel rooms for myself and all of the guests I had (10) coming in for the trip. Not a pleasant experience and very little communication other than there was a “maintenance problem”. "
United States
Timothy C.
The price is CA $3,182
CA $5,672 total
includes taxes & fees
Sep 13 - Sep 14
Waterfront Luxe Pool, Hot Tub, Theater, Gamesandmore
A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

5. Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (230 reviews)
"Love the place , only problem with out a gulf car the beach and fishing area is too far away"
United States
Dayanis
The price is CA $364
CA $795 total
includes taxes & fees
Sep 13 - Sep 14
Key Largo Kawama Villa L1, 3/3
A resort with a pool, palm trees, and a view of the ocean.

6. 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 $1,725
CA $3,404 total
includes taxes & fees
Sep 27 - Sep 28
PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key
A coastal resort with multiple bungalow-style buildings, a marina, and a large body of water.

7. 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 $577
CA $1,389 total
includes taxes & fees
Sep 16 - Sep 17
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
A covered outdoor area with a round table and chairs, a white railing, and a view of the ocean.

8. 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, (62 reviews)
"Excellent place,"
United States
MONICA A.
The price is CA $235
CA $694 total
includes taxes & fees
Sep 14 - Sep 15
Villa 5027 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.

9. 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 $262
CA $726 total
includes taxes & fees
Sep 14 - Sep 15
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

10. 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.
The price is CA $262
CA $709 total
includes taxes & fees
Sep 16 - Sep 17
Seas the Keys Getaway with plunge pool/spa
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, (4 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
The price is CA $630
CA $1,455 total
includes taxes & fees
Sep 16 - Sep 17
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
A deck with tables and chairs, overlooking a marina with boats and a body of water.

12. 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)
"Great location, well equipped unit!Worked out perfectly"
United States
David N.
The price is CA $262
CA $726 total
includes taxes & fees
Sep 15 - Sep 16
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.

13. 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 $235
CA $694 total
includes taxes & fees
Sep 16 - Sep 17
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
A living room with a view of the sea, a ceiling fan, a TV, and a dining area with outdoor seating.

14. 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, (7 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is CA $235
CA $694 total
includes taxes & fees
Sep 16 - Sep 17
Villa 5034 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.

15. 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 $235
CA $694 total
includes taxes & fees
Sep 16 - Sep 17
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

La Jolla Resort

La Jolla Resort

10/10 Excellent
"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t recommend this place more. It’s like a throwback to an earlier time, but completely updated. Plenty of restaurants to pick from nearby and the Islamorada Brewery across the street is great, and has a wonderful beer garden out back."
Michael 1-night trip
Posted 2 hours ago
La Jolla Resort

Find out more about Islamorada

Islamorada Villas information

Number of reviews
632
Accommodation
64 Villas
Lowest Price
CA $694
Highest Price
CA $5,672

Frequently asked questions

How much do villas in Islamorada cost?
Prices for villas in Islamorada range between CA $694 and CA $5,672 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.
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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