Title: Windward Side Vacation Rentals from CA $177: Short-Term Rentals for 2026 | Expedia.ca [Hotels in Windward Side](https://expedia.ca/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Things to do in Windward Side](https://expedia.ca/Things-To-Do-In-Windward-Side.d11638.Travel-Guide-Activities)[Windward Side Car Rentals](https://expedia.ca/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide)[Windward Side Vacation Packages](https://expedia.ca/Windward-Side.d11638.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Stills 'n' stories ![](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.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 ## Check prices for these dates In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=11638&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 three months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=11638&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) In four months [Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windward Side vacation rentals ![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/23cae97a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/adf0d71b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/d5b575ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/416dcc8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad [](https://www.expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information) Oranjestad 7.0/10 Good (2 reviews) "The appartment is spacious and has everything you need. It was very neat and clean and the host Davon fast in response. The location is a quiet neighbourhood, not far away from the center. Thanks for having us. " ![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg) sytske m. CA $188 CA $223 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/1d1cb7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/f67596c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/4c62066a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/288f1499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm Spring Inn [](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) Oranjestad 8.4/10 Very good (15 reviews) "Great place lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dameon CA $160 CA $177 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/c6a9a19c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/8a35946a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/9e2c7c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/a91d2951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad [](https://www.expedia.ca/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information) Oranjestad CA $188 CA $223 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/112b37fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/c0dd92a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/268182e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/f1a67479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views [](https://www.expedia.ca/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.Hotel-Information) Sint Eustatius CA $184 CA $267 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.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=2026-04-12&endDate=2026-04-13®ionId=11638&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=Windward+Side%2C+Saba%2C+Bonaire%2C+Sint+Eustatius+and+Saba®ionId=11638&latLong=17.628452%2C-63.231205&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windward+Side%2C+Saba%2C+Bonaire%2C+Sint+Eustatius+and+Saba®ionId=11638&latLong=17.628452%2C-63.231205&adults=2&startDate=2026-06-27&d1=2026-06-27&endDate=2026-06-30&d2=2026-06-30&lodging=COTTAGE) ![](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%2FWindward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals) ## Top Windward Side Hotel Reviews ![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0_y.jpg) ### Saba Arawak Hotel 6/10 Okay "Nice view, room clean (floor could be cleaner) and good, daily housekeeping. Connection with village is poor: although it is on short distance, as pedestrian it is very dangerous to walk roadside to restaurants and shops. A shuttle should be the best solution. " [](https://expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information) ![Peter Hytte is close to everything at great price!](https://images.trvl-media.com/lodging/90000000/89690000/89687400/89687379/c3956cf7_y.jpg) ### Peter Hytte is close to everything at great price! 10/10 Excellent "Our trip started with a cab pick up at the airport arranged by Jeff. He then met us at the property, showed us around and gave us some very good meal recommendations. We decided to venture up Mt Scenery the next day and unfortunately for me, I tripped 5 steps before finishing at the bottom and severely sprained both of my ankles. I texted Jeff and he came and picked us up and took us to the hospital. Jeff also came back to the hospital to pick us up and dropped us off again two days later for follow up. I can honestly say Jeff was the kindest VRBO host whose property we have stayed at. He is very knowledgeable about the island and seemingly knows everyone. Next time we go back, we will definitely stay at either Peter Hytte or Jeff’s even larger property next door! " [](https://expedia.ca/Windward-Side-Hotels-Peter-Hytte-Is-Close-To-Everything-At-Great-Price.h89687379.Hotel-Information) ![Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/43320e37_y.jpg) ### Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away! 10/10 Excellent "Althea Cottage was absolutely amazing! It is a historic chattel cottage located centrally within Windwardside village. It is a short walk away from the Busy Bee Bakery, which is a phenomenal place to enjoy breakfast, a snack, or lunch. It is also in close proximity to the grocery store and restaurants. The cottage overlooks the village, and you can also view the sea in the distance from both the right and left. The kitchen is very well equipped with everything you need to cook. The living room is very spacious and comfortable. The bedroom and bathroom are very well furnished. The cottage has the most wonderful patio area with table and chairs and is framed with a beautiful rock garden.Jeff was aa wonderful host! He was there to meet us when we arrived. He provided us a tour of the cottage and answered any questions that we had. He was available during our stay for any additional information that we requested. The people who live on Saba are very environmentally conscious. Jeff upholds and supports this vision and has set up his rental cottage to conserve water and recycle. It was refreshing in my opinion and made me really think about resources such as water and disposables.Saba is an amazing island and it's beauty surpasses much I have seen in the Caribbean. The hiking trails are phenomenal. I highly recommend staying at Althea cottage!" [](https://expedia.ca/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information) ![Palm Spring Inn](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/1d1cb7e6_y.jpg) ### Palm Spring Inn 6/10 Okay "Really convenient for the airport ... But slightly further from town than expect.. Some upgrading work happening so roof top barbeque area not accessible and some noise . However room clean and large kitchen area if needed. Everyone really helpful. " [](https://expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) ![The Old Gin House](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63_y.jpg) ### The Old Gin House 8/10 Good "There is no shuttle. Someone at the airport got us a taxi. The hotel did not help in any way in us getting to the hotel. Important to know.....you are on your own to and from the hotel. Heads up hotel.com would not let me post this" [](https://expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information) ![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/59c43c6c_y.jpg) ### El Momo Cottages 10/10 Excellent "Loved this place as so simply beautiful and relaxed. Not suitable if struggle with mobility as located up a steep hill / steps ... But worth the view. " [](https://expedia.ca/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information) ![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/cbfa65db_y.jpg) ### Flamboyant Cottage - Spectacular View & Pool 10/10 Excellent "We had a wonderful stay at Flamboyant Cottage. From the start communication was well defined and instant. The house manager Cece was so helpful and her assistant Marc was available to review the house and answer questions. Cece arranged a taxi to and from the airport. It made our travel very easy." [](https://expedia.ca/Windward-Side-Hotels-Beautiful-Gingerbread-Cottage-Spectacular-View-Pool.h34006194.Hotel-Information) ![ Quill Gardens Boutique Hotel](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb_y.jpg) ### Quill Gardens Boutique Hotel 10/10 Excellent "Great space and wonderful staff " [](https://expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information) ![Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/23cae97a_y.jpg) ### Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad 6/10 Okay "The staff was ok but they came late to open for me. While the property was generally up to standards there was not toilet tissue neither bathing soap. Did not.know i had to provide these myself." [](https://expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information) ## Find out more about Windward Side You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windward Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) ## Frequently asked questions ### Are there vacation rentals in Windward Side? ### What are some of the best vacation rentals that Windward Side has to offer? ### How many vacation rentals are there in Windward Side? ### What’s there to see and do in Windward Side? ### What’s a vacation rental in Windward Side like?