Title: Leeward Vacation Rentals from CA $3,918: Short-Term Rentals for 2026 | Expedia.ca

[Leeward Hotels](https://expedia.ca/Destinations-In-Leeward.d553248635975177495.Hotel-Destinations)[Leeward Car Rentals](https://expedia.ca/Destinations-In-Leeward.d553248635975177495.Car-Rental-Destinations)[Leeward Vacations](https://expedia.ca/Leeward.d553248635975177495.Destination-Travel-Guides)

![Anse des Cayes featuring landscape views, general coastal views and a coastal town](https://images.trvl-media.com/place/553248635975749415/bd30699a-067f-48d5-bfe7-8ade0f817f15.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635975749415/bd30699a-067f-48d5-bfe7-8ade0f817f15.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Our top choices for Leeward vacation rentals

![A heated pool](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/4331808b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1598h1067x0y0-bb575516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/a8a87f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1599h1066x1y1-c7417c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Vue mer Panoramique, à 5 Minute de la Plage !

[](https://www.expedia.ca/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information)

Anse des Cayes

9.8/10

Exceptional

(7 reviews)

"Wonderful stay! "

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

Tara T.

CA $3,910

CA $4,905 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.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=2026-02-21&endDate=2026-02-22&regionId=553248635975177495&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Leeward%2C+St.+Barthelemy&regionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Leeward%2C+St.+Barthelemy&regionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Leeward%2C+St.+Barthelemy&regionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Leeward%2C+St.+Barthelemy&regionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

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## Top Leeward Hotel Reviews

![Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool](https://images.trvl-media.com/lodging/91000000/90990000/90980500/90980438/96c5a83a_y.jpg)

### Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool

10/10 Excellent

"The location was great, the villa spotless and well equipped. The garden is charming."

[](https://expedia.ca/St-Barthelemy-Hotels-Rose-Des-Cayes-In-Saint-Barthelemy-With-Parking-And-Private-Pool.h90980438.Hotel-Information)

![Hotel Barrière Le Carl Gustaf St Barth](https://images.trvl-media.com/lodging/39000000/38820000/38812000/38811961/dc57b858_y.jpg)

### Hotel Barrière Le Carl Gustaf St Barth

10/10 Excellent

"Great property and staff.."

[](https://expedia.ca/St-Barthelemy-Hotels-Hotel-Barriere-Le-Carl-Gustaf-St-Barth.h38811961.Hotel-Information)

![Pearl Beach Hotel](https://images.trvl-media.com/lodging/1000000/60000/54000/53985/a3e17900_y.jpg)

### Pearl Beach Hotel

10/10 Excellent

"Our pickup and drop off at the ferry was perfect. The room was very clean. The restaurant served wonderful meals and the beach location was great. The whole staff were very friendly and helpful. We will be back!"

[](https://expedia.ca/St-Barthelemy-Hotels-Pearl-Beach-Hotel.h53985.Hotel-Information)

![GYP SEA Saint Barth](https://images.trvl-media.com/lodging/16000000/15990000/15981000/15980957/355efd8e_y.jpg)

### GYP SEA Saint Barth

10/10 Excellent

"Beautiful property, good food. Loved the decor. Having dedicated beach chairs at Gyp sea Beach club was a huge plus. The best beach in my opinion! Staff was so friendly and responsive. Would definitely stay here again."

[](https://expedia.ca/St-Barthelemy-Hotels-Hotel-Villa-Marie-Saint-Barth.h15980957.Hotel-Information)

![Reve de Saint Barth](https://images.trvl-media.com/lodging/89000000/88480000/88474800/88474775/57f48ebb_y.jpg)

### Reve de Saint Barth

10/10 Excellent

"If you’re looking for tranquility, elegance, and an authentic St. Barts escape, Le Rêve de Saint Barth is absolutely exceptional. A place you’ll want to return to again and again ✨"

[](https://expedia.ca/St-Barthelemy-Hotels-REVE-DE-SAINT-BARTH.h88474775.Hotel-Information)

![Villa Vue mer Panoramique, à 5 Minute de la Plage !](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1600h1066x0y1-f6b080e6_y.jpg)

### Villa Vue mer Panoramique, à 5 Minute de la Plage !

10/10 Excellent

"The property has an amazing view and the staff was so friendly and helpful. Highly recommend!"

[](https://expedia.ca/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information)

![On the Beach, in Saint Barth... Villa Mellow Mood](https://images.trvl-media.com/lodging/75000000/74740000/74735400/74735317/23bc1617_y.jpg)

### On the Beach, in Saint Barth... Villa Mellow Mood

10/10 Excellent

"Oh my! The host, Jean, was the absolute BEST! He was so welcoming and helpful and was one of the highlights of our stay on St Barths! The home was beautiful - amazing views, comfortable beds, beautiful kitchen and living room AND a workout room and hot tub. We’d stay there again in a second. Lovely! "

[](https://expedia.ca/St-Barthelemy-Hotels-On-The-Beach.h74735317.Hotel-Information)

![SUNSET VILLA ANGEL ****](https://images.trvl-media.com/lodging/47000000/46380000/46376300/46376295/c65b3662_y.jpg)

### SUNSET VILLA ANGEL \*\*\*\*

10/10 Excellent

"Great spot for a romantic stay for two! Right next to Petite Colombe bakery and Bananiers, so close they’re walkable. 5 minute drive to Gustavia. Beautiful views! Definitely would book again! "

[](https://expedia.ca/St-Barthelemy-Hotels-SUNSET-VILLA-ANGEL.h46376295.Hotel-Information)

![Luxury villa with magnificent sea view](https://images.trvl-media.com/lodging/91000000/90310000/90309200/90309101/4190ffda_y.jpg)

### Luxury villa with magnificent sea view

10/10 Excellent

"The villa was so beautiful. Surrounded by water and had everything we could possibly ever need. Didn’t want to leave. The cleaning ladies were so friendly and enjoyable to talk too. Great place to relax and just de-stress from everyday life. "

[](https://expedia.ca/St-Barthelemy-Hotels-Luxury-Villa-Offering-A-Magnificent-Sea-View.h90309101.Hotel-Information)

## Find out more about Leeward

**Everything you need to know about** **Leeward** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leeward vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leeward vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Leeward vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Leeward. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leeward vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Leeward vacation rentals we have selected for you start as low as CA $3,918 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Leeward rentals**

At Expedia, we put the best Leeward vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leeward rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leeward vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leeward. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Popular Leeward Cities

- [St. Barthelemy Vacation Rentals ](https://expedia.ca/St-Barthelemy-Vacation-Rentals.d6140949.Travel-Guide-VacationRentals)