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 [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=11638&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=11638&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/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 four months [Jun 19 - Jun 21](https://www.expedia.com/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) ## 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) ![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) ![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) ### Palm Spring Inn [](https://www.expedia.com/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information) Oranjestad 8.6/10 Excellent (14 reviews) "Great place lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dameon $120 nightly $128 total Feb 24 - Feb 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=2026-03-09&endDate=2026-03-10®ionId=11638&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_11638) ## 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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&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 ![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/738de9aa_y.jpg) ### Saba Arawak Hotel 10/10 Excellent "Well organised very clean room, nice balcony. Good wifi. the room had more kitchen equipment than expected, very convenient." [](https://expedia.com/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information) ![ Quill Gardens Boutique Hotel](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/c6c425a2_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) ![Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/a524e520_y.jpg) ### Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away! 10/10 Excellent "My husband and I enjoyed a wonderful stay in this comfortable, well situated and historic cottage. Our host, Jeff, was extraordinary, providing an excellent orientation to beautiful Saba and informing us about everything we needed to know to maximize our brief time on the island. His referrals to restaurants and activities were perfect. We look forward to returning as soon as we can!" [](https://expedia.com/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information) ![The Old Gin House](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/e4b10408_y.jpg) ### The Old Gin House 10/10 Excellent "Very awesome hotel, great history and staff was excellent, great job." [](https://expedia.com/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information) ![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/3c3130af_y.jpg) ### Flamboyant Cottage - Spectacular View & Pool 10/10 Excellent "Lovely cabin with incredible view. " [](https://expedia.com/Windward-Side-Hotels-Beautiful-Gingerbread-Cottage-Spectacular-View-Pool.h34006194.Hotel-Information) ![Talk of the Town Inn & Suites](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/ecfb3641_y.jpg) ### Talk of the Town Inn & Suites 10/10 Excellent "The Talk of the Town is a stunning nice, cosy hotel with a small compound of summer houses and swimming pool. Most exciting and many thanks! Raymond" [](https://expedia.com/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information) ![Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/2a7adee1_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) ![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/33fcc0f7_y.jpg) ### El Momo Cottages 10/10 Excellent "The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!" [](https://expedia.com/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information) ![Peter Hytte is close to everything at great price!](https://images.trvl-media.com/lodging/90000000/89690000/89687400/89687379/465c91ea_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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