Title: Windley Key Villas from CA $1,455 | Expedia.ca

[Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)

![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windley Key villas

![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67390000/67389700/67389654/1e3af2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67390000/67389700/67389654/b484f538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/68000000/67390000/67389700/67389654/3d66974c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67390000/67389700/67389654/782de557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Overlooking Saltwater Lagoon Free Kayaks Renovated

[](https://www.expedia.ca/Key-Largo-Hotels-Overlooking-Saltwater-Lagoon-Free-Kayaks-Renovated.h67389654.Hotel-Information)

Key Largo

9.6/10

Exceptional

(46 reviews)

"Absolutely perfect trip. The house was clean and had everything we needed. Its a great location too!"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Jill D.

CA $464

CA $1,192 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Key-Largo-Hotels-Overlooking-Saltwater-Lagoon-Free-Kayaks-Renovated.h67389654.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365464/4b2d06b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365464/7a574d2d_edited_1904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365464/1d9bf301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365464/d435eb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lagoon View Free Kayaks Pool Playground Pickle Ball

[](https://www.expedia.ca/Key-Largo-Hotels-Lagoon-View-Free-Kayaks-Pool-Playground-Pickle-Ball.h100365464.Hotel-Information)

Key Largo

9.2/10

Wonderful

(14 reviews)

"Thanks for a wonderful stay!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tracey D.

CA $449

CA $1,079 total

includes taxes & fees

Mar 14 - Mar 15

[](https://www.expedia.ca/Key-Largo-Hotels-Lagoon-View-Free-Kayaks-Pool-Playground-Pickle-Ball.h100365464.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74740000/74730800/74730716/e0e30a1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74740000/74730800/74730716/bcddc29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/75000000/74740000/74730800/74730716/3a9b4174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74740000/74730800/74730716/caabd78e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Overlooking Pool Free Golf Cart Free Kayaks Pickleball

[](https://www.expedia.ca/Key-Largo-Hotels-Overlooking-Pool-Free-Golf-Cart-Free-Kayaks-Pickleball.h74730716.Hotel-Information)

Key Largo

9.4/10

Exceptional

(38 reviews)

"The house was perfect to accommodate all of us and the location was great! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly H.

CA $567

CA $1,402 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Key-Largo-Hotels-Overlooking-Pool-Free-Golf-Cart-Free-Kayaks-Pickleball.h74730716.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365457/a684661a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365457/2d3324ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365457/618e021c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365457/5b2b8810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanview Marinaview Free Golf Cart Pool Pickleball

[](https://www.expedia.ca/Key-Largo-Hotels-Oceanview-Marinaview-Free-Golf-Cart-Pool-Pickleball.h100365457.Hotel-Information)

Key Largo

10/10

Exceptional

(65 reviews)

"Beautiful views and great location! Enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathy A.

CA $689

CA $1,556 total

includes taxes & fees

Mar 20 - Mar 21

[](https://www.expedia.ca/Key-Largo-Hotels-Oceanview-Marinaview-Free-Golf-Cart-Pool-Pickleball.h100365457.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99250000/99247900/99247820/ca82991c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/100000000/99250000/99247900/99247820/c5792774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99250000/99247900/99247820/b993de83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99247900/99247820/32389b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanview • Pool View • Indoor/Outdoor Pickleball

[](https://www.expedia.ca/Key-Largo-Hotels-Oceanview-Pool-IndoorOutdoor-Pickleball-September-Deals.h99247820.Hotel-Information)

Rock Harbor

9.6/10

Exceptional

(23 reviews)

"Great place to stay! View was great, place was clean, pools were awesome! Definitely worth booking!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert F.

CA $615

CA $1,627 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Key-Largo-Hotels-Oceanview-Pool-IndoorOutdoor-Pickleball-September-Deals.h99247820.Hotel-Information)

![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Islands of Islamorada

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

Matecumbe

9.8/10

Exceptional

(71 reviews)

"Beautiful accommodations and location, very clean, many activities available at resort"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janet

CA $1,226

CA $1,455 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/fa352cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/66c9cec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/08e34661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/863e0ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Luxe Pool, Hot Tub, Theater, Gamesandmore

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Luxe-Pool.h122581357.Hotel-Information)

Buccaneer Point

CA $3,137

CA $4,800 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Luxe-Pool.h122581357.Hotel-Information)

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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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Private vacation homes

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Condos

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Cottages

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Villas

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Houseboats

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## Top Windley Key Hotel Reviews

![Sunset Cove Beach Resort](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae_y.jpg)

### Sunset Cove Beach Resort

10/10 Excellent

"We stayed in Cottage 3, and absolutely loved it. It was well kept, clean, and comfortable. The property is very convenient, with the beach, office, and cottages all easy to walk to from any point on the property within a minute. The staff was kind and helpful, and the light breakfast was a nice touch. Highly recommend staying here. "

[](https://expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information)

![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg)

### Chesapeake Beach Resort

10/10 Excellent

"Very comfortable with nice rooms. Attentive on site management."

[](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information)

![Holiday Inn Key Largo by IHG](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg)

### Holiday Inn Key Largo by IHG

10/10 Excellent

"Room was updated and clean. We loved the pool area and tiki bar atmosphere. Clean facility!"

[](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information)

![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg)

### Amara Cay Resort

10/10 Excellent

"Staff excellent. Clean room and surroundings "

[](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)

![Playa Largo Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg)

### Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"The resort is very relaxing and beautiful. The welcome mojito set the vibe. We traveled with our 10 month old infant who had a wonderful time in the pool and beach. The rooms were large and clean. Requested a first floor patio and was assigned one. It really helped not having to do an elevator with our stroller, and having easy access to the pool "

[](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information)

![Bayside Inn Key Largo](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg)

### Bayside Inn Key Largo

10/10 Excellent

"Clean and comfortable. Said bay view but no view from room of bay. Super short walk to bay with a beautiful view and nice place to chill though. Great to have Snooks right next door for good food. "

[](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information)

![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg)

### Marina Del Mar Resort and Marina

10/10 Excellent

"This was beautiful. We loved it here we loved how close everything was to town. Staff was friendly and nice. Love the little gift shop on property. "

[](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information)

![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg)

### Drop Anchor

10/10 Excellent

"My stay at Drop Harbor was excellent. The room was spotless and the location couldn’t have been better. I opened my door and the water was right there — absolutely beautiful. The front desk staff was very friendly and welcoming. Overall, a fantastic experience!"

[](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information)

![Lime Tree Bay Resort](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8_y.jpg)

### Lime Tree Bay Resort

10/10 Excellent

"The room was clean, small but very usable with nice updating of tile and bath. It is right on the bay, with beautiful sunsets! The pool area is very nice with a great view of the bay!! "

[](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information)

## Find out more about Windley Key

## Windley Key Villas information

| Number of reviews | 71        |
| ----------------- | --------- |
| Accommodation     | 57 Villas |
| Lowest Price      | CA $1,455 |
| Highest Price     | CA $1,455 |

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