Title: Windward Vacation Rentals : Search Short-Term Rentals | Expedia.com [Windward Hotels](https://expedia.com/Destinations-In-Windward.d553248635975177497.Hotel-Destinations)[Windward Flights](https://expedia.com/Destinations-In-Windward.d553248635975177497.Flight-Destinations)[Car Rentals in Windward](https://expedia.com/Destinations-In-Windward.d553248635975177497.Car-Rental-Destinations)[Windward Vacations](https://expedia.com/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_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 ## Our top choices for Windward vacation rentals ![A heated pool](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/4331808b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1600h1066x0y1-15516b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/a8a87f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1598h1067x0y0-bb575516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Anse des Cayes [](https://www.expedia.com/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) 9.8/10 Exceptional (9 reviews) "Wonderful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara T. $3,265 nightly $3,579 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/32000000/31370000/31368900/31368803/a9b509e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31370000/31368900/31368803/b1ec72b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31370000/31368900/31368803/cd9b964e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, stereo, computer monitors](https://images.trvl-media.com/lodging/32000000/31370000/31368900/31368803/b1f4c28d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Anse des Cayes [](https://www.expedia.com/St-Barthelemy-Hotels-BEACH-VILLA-CENTRAL-LOCATION-BETW-ST-JEAN-FLAMMANS-BEACH-4-Min-TO-CITY.h31368803.Hotel-Information) 10/10 Exceptional (10 reviews) "We had a wonderful stay at this beautiful place on the beach. Joce was very friendly and helpful - he even drove some of us to the airport when we couldn't fit all of our bags in the car. The place is so relaxing and beautiful, we had trouble leaving even to see other parts of the island." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd G. $2,627 nightly $2,747 total Mar 7 - Mar 8 Total with taxes and fees [](https://www.expedia.com/St-Barthelemy-Hotels-BEACH-VILLA-CENTRAL-LOCATION-BETW-ST-JEAN-FLAMMANS-BEACH-4-Min-TO-CITY.h31368803.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=2026-03-10&endDate=2026-03-11®ionId=553248635975177497&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_553248635975177497) ## Find vacation rentals that suit your style Villas [](https://www.expedia.com/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Windward%2C+St.+Barthelemy®ionId=553248635975177497&latLong=17.898425%2C-62.816958&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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%2FDestinations-In-Windward.d553248635975177497.Vacation-Rental-Destinations)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windward.d553248635975177497.Vacation-Rental-Destinations) ## Top Windward Hotel Reviews ![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 "The house was beautiful with fabulous views!! It was clean and the beds were super comfortable. The kitchen was well equipped with everything we needed. The host was very kind and attentive. " [](https://expedia.com/St-Barthelemy-Hotels-St-Barts-New-Luxury-Villa-Roc-E-Mar.h18992616.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 "The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone! " [](https://expedia.com/St-Barthelemy-Hotels-Tropical-Hotel-St-Barth.h6956.Hotel-Information) ![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.com/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.com/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.com/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.com/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.com/St-Barthelemy-Hotels-Christopher-Hotel.h9481.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.com/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.com/St-Barthelemy-Hotels-Bougainvilliers-Very-Private-And-Charming-Villa-With-Sea-View-Close-To-The-Beach.h29621328.Hotel-Information) ## Find out more about Windward ## Discover your perfect Windward vacation rental with Expedia #### How many vacation rentals are available in Windward? Expedia has plenty of vacation rentals to choose from in and around Windward, so you’re guaranteed to find the right one for you. #### How much is a vacation rental in Windward? 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! #### What type of vacation rental can I get in Windward? Vacation rentals in Windward come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windward vacation rentals to suit everyone. #### Why should I choose a vacation rental in Windward? Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windward vacation rental often works out to be a fantastic, cost-effective option for [groups](https://www.expedia.com/lp/b/vr/large) and [families](https://www.expedia.com/lp/b/vr/family) 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. #### How do I find the best deal on a vacation rental in Windward? Find vacation rentals in Windward by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windward. #### What amenities are available in a vacation rental in Windward? The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a [swimming pool](https://www.expedia.com/lp/b/vr/private-pool) is more your thing. Of course, there’s always the treat of having [your own hot tub](https://www.expedia.com/lp/b/vr/hot-tub). Expedia has a vast range of amenities in Windward vacation rentals designed to suit every budget and trip type. #### When is the best time to stay in a vacation rental in Windward? Everytime is a great time to head to Windward! Staying in a Windward vacation rentals you will always find lots going on to keep you entertained. #### Why book a vacation rental with Expedia? Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windward. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windward vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windward, you can save even more. #### Can I cancel my vacation rental through Expedia? Yes, you can cancel or change your Windward vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted. ## Explore a world of travel with Expedia - Popular Windward Cities - [St. Barthelemy Vacation Rentals ](https://expedia.com/St-Barthelemy-Vacation-Rentals.d6140949.Travel-Guide-VacationRentals)