Title: Windward Side Vacation Rentals from $128: Search Short-Term Rentals | Expedia.com [Windward Side Travel Guide](https://expedia.com/Windward-Side.dx11638)[Hotels in Windward Side](https://expedia.com/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Flights to Windward Side](https://expedia.com/Cheap-Flights-To-Windward-Side.d11638.Travel-Guide-Flights)[Car Rentals in Windward Side](https://expedia.com/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide)[Windward Side Vacation Packages](https://expedia.com/Windward-Side.d11638.Destination-Travel-Guides) ![The beautiful island of Saba](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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=11638&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 two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=11638&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=11638&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=11638&startDate=2026-07-10&endDate=2026-07-12&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 ![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) ![Suite, 2 Bedrooms | Private kitchenette | Full-size fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/2c07626c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Individually decorated, individually furnished, soundproofing](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/288f1499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Oranjestad [](https://www.expedia.com/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) 8.4/10 Very Good (15 reviews) "Great place lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dameon $120 nightly $128 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.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.com/Hotel-Search?startDate=2026-04-04&endDate=2026-04-05®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.com/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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=APARTMENT) Cottages [](https://www.expedia.com/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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals) ## Top Windward Side Hotel Reviews ![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.com/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.com/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.com/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.com/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information) ![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0_y.jpg) ### Saba Arawak Hotel 8/10 Good "It's on the windward side of the island...realize that!!!! Staff is really nice, the hike to "town" (no shops, few restaurants) is easy.." [](https://expedia.com/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.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.com/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.com/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.com/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.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 "It's safe to say I could absolutely live here!!! This cottage is in the heart! Jeffery is amazing. He's helpful, laid back and kind LIKE EVERYONE here! I'm booking again soon. Where else can you sleep with all your doors and windows open in nature and be safe?" [](https://expedia.com/Windward-Side-Hotels-Peter-Hytte-Is-Close-To-Everything-At-Great-Price.h89687379.Hotel-Information) ## Find out more about Windward Side **Everything you need to know about Windward Side 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 Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Windward Side vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windward Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windward Side in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Windward Side rentals** At Expedia, we put the best Windward Side 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 Side 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 Side 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 Side. 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 - Trending destinations on Expedia.com ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) ## Frequently asked questions ### Are there vacation rentals in Windward Side? 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