Title: Windley Key Villas from CA $1,241 | 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

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-05-29&endDate=2026-05-31&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

![Exterior](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/fa352cf8.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)

![Dining](https://images.trvl-media.com/lodging/123000000/122590000/122581400/122581357/w1619h1077x0y3-6f06330b.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 $3,138

CA $4,801 total

includes taxes & fees

Feb 10 - Feb 11

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

(70 reviews)

"Amazing stay, can’t wait to stay there again!"

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

Anonymous traveller

CA $1,229

CA $1,458 total

includes taxes & fees

Feb 26 - Feb 27

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

![Exterior](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/dbe96b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/aaa95a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/2d0fd435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72660000/72653600/72653526/3c06d12a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Oceanside Mariner\`s 3 Bedroom Townhome

[](https://www.expedia.ca/Key-Largo-Hotels-Beautiful-Oceanside-Mariners-3-Bedroom-Townhome.h72653526.Hotel-Information)

Rock Harbor

10/10

Exceptional

(91 reviews)

"Great place, great hosts. We'll probably be backThank you"

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

Curt B.

CA $681

CA $1,241 total

includes taxes & fees

Mar 6 - Mar 7

[](https://www.expedia.ca/Key-Largo-Hotels-Beautiful-Oceanside-Mariners-3-Bedroom-Townhome.h72653526.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71790000/71785400/71785374/665bdff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/72000000/71790000/71785400/71785374/ef62f45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, beach towels](https://images.trvl-media.com/lodging/72000000/71790000/71785400/71785374/e91fd44d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/72000000/71790000/71785400/71785374/5652b6d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Golf Cart Free Kayaks Steps to Pool Pickleball

[](https://www.expedia.ca/Key-Largo-Hotels-Free-Golf-Cart-Free-Kayaks-Steps-To-Pool-Pickleball.h71785374.Hotel-Information)

Key Largo

9.6/10

Exceptional

(87 reviews)

"We had a great time"

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

Tania R.

CA $563

CA $1,320 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Key-Largo-Hotels-Free-Golf-Cart-Free-Kayaks-Steps-To-Pool-Pickleball.h71785374.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365461/d53ea95a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365461/e1b78cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365461/5a6840f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100370000/100365500/100365461/fc0bdc34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Lagoon Retreat | Kayaks • Paddleboard • Golf Cart

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Lagoon-Retreat-Kayaks-Paddleboard-Golf-Cart.h100365461.Hotel-Information)

Key Largo

9.8/10

Exceptional

(6 reviews)

"This is a great place to stay! This complex is full of very friendly people- cool location right on the lagoon, with a jetty a short golf cart ride or walk away!! Two pools and a wadable beach at the lagoon. Lots of great restaurants and bars nearby- twas a great vacation for us!! "

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

Kris I.

CA $543

CA $1,198 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Lagoon-Retreat-Kayaks-Paddleboard-Golf-Cart.h100365461.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/a1921f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis](https://images.trvl-media.com/lodging/100000000/99250000/99247900/99247820/99e52c87.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/100000000/99250000/99247900/99247820/971b6880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oceanview - Pool Indoor/Outdoor Pickleball September Deals

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

Rock Harbor

9.6/10

Exceptional

(20 reviews)

"We got what we were looking for a nice relaxing weekend and the place felt like home. Great views and location."

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

Alberto R.

CA $749

CA $1,799 total

includes taxes & fees

Feb 25 - Feb 26

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-18&endDate=2026-02-19&regionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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Private vacation homes

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Cottages

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Villas

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Houseboats

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## Top Windley Key Hotel Reviews

![Rock Reef Resort](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg)

### Rock Reef Resort

10/10 Excellent

"The staff are amazing; very friendly and helpful. We loved our stay and plan on coming back! "

[](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information)

![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg)

### Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"Clean room and the view was spectacular "

[](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information)

![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg)

### The Pelican Key Largo Cottages

10/10 Excellent

"Friendly staff and beautiful spot "

[](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.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

"Staff was very helpful and polite. Rooms clean. Loved our stay!"

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

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg)

### Waterside Suites & Marina

10/10 Excellent

"Our room was huge! Two floors, a bath and half and a full kitchen. Loved the view from the balcony. "

[](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information)

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg)

### Fisher Inn Resort & Marina

10/10 Excellent

"The room was so clean. I loved the whole resort. The view was amazing. The grounds were very well maintained. I will always stay at Fisher inn when I visit Islamorada "

[](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information)

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

### Chesapeake Beach Resort

10/10 Excellent

"Awesome place!!"

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

![Ocean Pointe Suites at Key Largo](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/c6c81bd5_y.jpg)

### Ocean Pointe Suites at Key Largo

10/10 Excellent

"The walls, doors, and baseboards could use a good scrub and maybe some fresh paint. Otherwise, it was very nice. "

[](https://expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.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

"Another awesome stay. Staff was very friendly and helpful, location is great and check in check out was super easy and fast!"

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

## Find out more about Windley Key

## Windley Key Villas information

| Number of reviews | 247       |
| ----------------- | --------- |
| Accommodation     | 57 Villas |
| Lowest Price      | CA $1,241 |
| Highest Price     | CA $1,458 |

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- [Vacation Homes in Upper Matecumbe Key ](https://www.expedia.ca/Upper-Matecumbe-Key-Private-Vacation-Homes.d553248635975749648-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [History of Diving Museum ](https://www.expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction)
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- [Visit Venetian Shores ](https://www.expedia.ca/Islamorada-Venetian-Shores.dx553248635976470270)
- [Visit Plantation Key ](https://www.expedia.ca/Plantation-Key.dx553248635083898347)
- [Windley Key Fossil Reef Geological State Park ](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

- [Avis Rental Cars in Plantation Key ](https://www.expedia.ca/Avis-Car-Rentals-In-Plantation-Key.d553248635083898347-c41.Car-Rental-Guide-Suppliers)
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- [Book Villas in Windley Key on Expedia.com ](https://www.expedia.com/Windley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)