--- title: "Windward Side Vacation Home Rentals from CA $570: Search Top Private Vacation Homes for Rent | Expedia.ca" description: "Book the best Vacation Homes in Windward Side in 2026. Compare rates from CA $570, guest reviews and availability of 2 stays. Most stays are fully refundable." canonical: "https://www.expedia.ca/Windward-Side-Private-Vacation-Homes.d11638-aaPrivateVacationHomes.Travel-Guide-Accommodation" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-15T17:01:01Z --- Plan your trip - [Windward Side Travel Guide](https://www.expedia.ca/Windward-Side.dx11638) - [Hotels in Windward Side](https://www.expedia.ca/Windward-Side-Hotels.d11638.Travel-Guide-Hotels) - [Flights to Windward Side](https://www.expedia.ca/Cheap-Flights-To-Windward-Side.d11638.Travel-Guide-Flights) - [Things to do in Windward Side](https://www.expedia.ca/Things-To-Do-In-Windward-Side.d11638.Travel-Guide-Activities) - [Car Rentals in Windward Side](https://www.expedia.ca/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide) - [Windward Side Vacation Packages](https://www.expedia.ca/Windward-Side.d11638.Destination-Travel-Guides) - [Vacation Rentals in Windward Side](https://www.expedia.ca/Windward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals) # Windward Side Vacation Rentals ![A lush green mountain with a white picket fence and buildings with red roofs.](https://images.trvl-media.com/place/11638/7417c27a-6e71-4a67-bfcb-b2adf33a9159.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Find vacation rentals that suit your style [Apartments](https://www.expedia.ca/Hotel-Search?destination=Windward%20Side,%20Saba,%20Bonaire,%20Sint%20Eustatius%20and%20Saba®ionId=11638&latLong=17.628452,-63.231205&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=APARTMENT) [Condos](https://www.expedia.ca/Hotel-Search?destination=Windward%20Side,%20Saba,%20Bonaire,%20Sint%20Eustatius%20and%20Saba®ionId=11638&latLong=17.628452,-63.231205&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=CONDO) ## Check prices for these dates [Check prices for these dates, December 15–16, 2026](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-12-15&endDate=2026-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&lodging=VACATION%5FHOME) [View in a map](https://www.expedia.ca/Hotel-Search?regionId=11638&stayLength=1&daysInFuture=30&pwaOverlay=map) ## Our top choices for Windward Side vacation homes ### [1\. Home a way from home in the Unspoiled queen of the Caribbean.](https://www.expedia.ca/Windward-Side-Hotels-Home-A-Way-From-Home-In-The-Unspoiled-Queen-Of-The-Caribbean.h73234367.Hotel-Information) ![A pool with lounge chairs and a stone patio, surrounded by lush greenery and overlooking a hilly landscape.](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234367/5c40b14b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Saba - Guest rating: 10/10 (Exceptional, 4 reviews) - Price: CA $571, CA $621 total, includes taxes & fees, Dec 1 - Dec 2, for Our top choices for Windward Side vacation homes - Review: The house was amazing we will be back again… Thank you Michael!, by Tim L. 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://www.expedia.ca/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30®ionId=11638&adults=2&sort=VACATION%5FRENTAL&openPlayBack=true) ## Learn more about Windward Side Colourful cottages with red roofs dot this charming village where hikers begin their ascent of Mount Scenery. Grab a meal at Scout's Place after exploring the Saba Conservation Foundation's trail network that winds through cloud forests. [See all hotels in Windward Side](https://www.expedia.ca/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30&adults=2®ionId=11638) ![A lush green mountain with a white picket fence and buildings with red roofs.](https://images.trvl-media.com/place/11638/7417c27a-6e71-4a67-bfcb-b2adf33a9159.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top reviews in Windward Side ### [Saba Arawak Hotel](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information) ![A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Windward Side - Review: Travelling to Saba was on our "bucket list". We knew where it was but not much else. This is a small island and not a resort experience. If you like to hike then this is the place. Same with diving. Leave your expectations at home. We stayed at the Arawak Hotel for 4 nights in late October. We had a one bedroom with a partial kitchen. The location was great, the view fantastic, and the Hotel quaint. The Arawak is being upgraded constantly but supplies are hard to get on Saba, so be..., by Duane, December 11, 2023, rated 10/10 Excellent ### [Quill Gardens Boutique Hotel](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information) ![A rectangular pool with clear blue water, surrounded by a wooden deck and white railings.](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/81c0f942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Oranjestad - Review: Our stay at Quill Gardens Estate was superb. Stunning views of the island, tranquil property, and very clean rooms. There was an excellent breakfast provided every morning (with vegetarian options). Only a 20 minute walk to the trailhead for The Quill, and a 25 minute walk to downtown Oranjestad. Carol, the hotel manager, was very welcoming and made us feel right at home as soon as we arrived. It's rare to find such personable and perceptive hospitality. As a gay couple, we found this to be a..., by Matt, June 9, 2023, rated 10/10 Excellent ### [The Old Gin House](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information) ![A beach with palm trees, a stone wall, and a building in the background.](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Oranjestad - Review: Very nice suite with large sitting room containing two sofas and a separate bedroom with king size sleigh bed. Although there had obviously been some money spent on this hotel, it was probably 20 years back and is now looking a bit tired. The staff were great and the restaurant was excellent, but it is essential to book a table when you first check in. If your taste is for Marriott style hotels, this may not be for you, but if you enjoy quirky originality and local flavour, you will be..., by Meredith John, February 18, 2026, rated 8/10 Good