Title: Windward Vacation Rentals : Short-Term Rentals for 2026 | Expedia.ca [Windward Hotels](https://expedia.ca/Destinations-In-Windward.d553248635975177497.Hotel-Destinations)[Windward Car Rentals](https://expedia.ca/Destinations-In-Windward.d553248635975177497.Car-Rental-Destinations)[Windward Vacations](https://expedia.ca/Windward.d553248635975177497.Destination-Travel-Guides) ![If ever around Eden Rock, make sure you walk all the way up for the best views!](https://images.trvl-media.com/place/6140949/35944ccf-824c-46b1-b4d5-faf1b8c89567.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Levente Láng ![](https://images.trvl-media.com/place/6140949/35944ccf-824c-46b1-b4d5-faf1b8c89567.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windward.d553248635975177497.Vacation-Rental-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windward.d553248635975177497.Vacation-Rental-Destinations) ## Top Windward Hotel Reviews ![Amnios St Barth](https://images.trvl-media.com/lodging/9000000/8820000/8818100/8818026/ad15bad2_y.jpg) ### Amnios St Barth 10/10 Excellent "We had a great experience in Saint " [](https://expedia.ca/St-Barthelemy-Hotels-Hotel-Villa-Lodge-4-Epices.h8818026.Hotel-Information) ![Hotel Les Ondines Sur La Plage](https://images.trvl-media.com/lodging/11000000/10660000/10658400/10658309/a3c346b1_y.jpg) ### Hotel Les Ondines Sur La Plage 10/10 Excellent "This was a wonderful stay, the attentive staff, cleanliness, breakfast and overall experience was just perfect! I would highly recommend this hotel & would gladly return!" [](https://expedia.ca/St-Barthelemy-Hotels-Hotel-Les-Ondines-Sur-La-Plage.h10658309.Hotel-Information) ![Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool](https://images.trvl-media.com/lodging/83000000/82820000/82812000/82811963/89dbb3cc_y.jpg) ### Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool 10/10 Excellent "This immaculate apartment is a marvel of design, function, and good taste. There is but one caveat - from the reserved parking spot, one must climb 60 stone steps to reach the front door. My husband and I are 81 years old and by the 3rd day we had mastered the climb, but it is worth noting. Once inside, the views of the bay are glorious. The apartment has two levels — be careful going up and down. The bedroom and full bath are upstairs — the bed is very comfortable and the open bathroom with its modern shower and double sinks comes with thick towels. Downstairs, there is a half bath and a washer and dryer. the kitchen is furnished with nice dishes and silverware and plentiful pots & pans. We especially appreciated the full jar of Nescafe and the bouilloire. The living area has a great view and is comfortable with a tv mounted across from the sofa. Wifi is excellent. The owner was available via WhatsApp and reached out several times to make sure all was ok. This is a wonderful unit — one we would definitely book again." [](https://expedia.ca/St-Barthelemy-Hotels-Luxury-Apartment-Stunning-Views-5-Minutes-From-Saint-Jean-Beach-Swimming-Pool.h82811963.Hotel-Information) ![Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente](https://images.trvl-media.com/lodging/101000000/100050000/100046400/100046394/34cc7bca_y.jpg) ### Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente 10/10 Excellent "I had a wonderful stay at Indigold. The room was very clean, comfortable, and well organized, with a great sense of privacy. The location is perfect—just a short walk from the beach—which made everything very convenient. The relaxation area was a lovely bonus and added to the overall calm and pleasant atmosphere. Everything was smooth and easy, and I truly felt at home. I would definitely recommend this place and would happily stay again." [](https://expedia.ca/St-Barthelemy-Hotels-Indigold-A-Deux-Pas-De-La-Plage-Chambre-Independante-Avec-Espace-Detente.h100046394.Hotel-Information) ![Christopher Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9481/4be4cba9_y.jpg) ### Christopher Hotel 10/10 Excellent "Great rooms, service and amenities! " [](https://expedia.ca/St-Barthelemy-Hotels-Christopher-Hotel.h9481.Hotel-Information) ![Tropical Hotel St Barth](https://images.trvl-media.com/lodging/1000000/10000/7000/6956/c0efe738_y.jpg) ### Tropical Hotel St Barth 10/10 Excellent "Great hotel! This is our second year in a row coming and it continues to get better every time. The staff is so warm and welcoming. Whether assisting with reservations on the island or helping you get a steamer the staff is quick and attentive. The food here is so underrated!! The burger was excellent. The location can’t be beat as your steps away from Eden rock, Nikki beach, le geurite and more! Must stay !" [](https://expedia.ca/St-Barthelemy-Hotels-Tropical-Hotel-St-Barth.h6956.Hotel-Information) ![La Maison Fleur de Lune](https://images.trvl-media.com/lodging/103000000/102900000/102896200/102896193/6b9d585e_y.jpg) ### La Maison Fleur de Lune 10/10 Excellent "Amazing little villa! Excellent location and shper friendly owners and staff. Almost feels more like a retreat with community breakfast and family like feel. Loved my room with an outdoor but private kitchette and lounge area. Absolutely fantastic!!!" [](https://expedia.ca/St-Barthelemy-Hotels-La-Reserve-Des-Salines.h102896193.Hotel-Information) ![BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach](https://images.trvl-media.com/lodging/30000000/29630000/29621400/29621328/40a11738_y.jpg) ### BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach 10/10 Excellent "Beautiful home" [](https://expedia.ca/St-Barthelemy-Hotels-Bougainvilliers-Very-Private-And-Charming-Villa-With-Sea-View-Close-To-The-Beach.h29621328.Hotel-Information) ![St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive](https://images.trvl-media.com/lodging/19000000/19000000/18992700/18992616/43fa03f4_y.jpg) ### St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive 10/10 Excellent "Always a memorable stay at Villa Roc e Mar! Can’t wait for our return in April! Thank you Goran!" [](https://expedia.ca/St-Barthelemy-Hotels-St-Barts-New-Luxury-Villa-Roc-E-Mar.h18992616.Hotel-Information) ## Find out more about Windward **Everything you need to know about** **Windward** **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 Windward 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 Windward vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Windward vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windward. 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 Windward 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 Windward vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Windward rentals** At Expedia, we put the best Windward 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 Windward 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 Windward 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 Windward. 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 Windward Cities - [St. Barthelemy Vacation Rentals ](https://expedia.ca/St-Barthelemy-Vacation-Rentals.d6140949.Travel-Guide-VacationRentals)