Title: Holiday Rentals Windward : Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Windward Hotels](https://expedia.co.uk/Destinations-In-Windward.d553248635975177497.Hotel-Destinations)[Windward Car Hire](https://expedia.co.uk/Destinations-In-Windward.d553248635975177497.Car-Hire-Destinations)[Windward Holidays](https://expedia.co.uk/Windward.d553248635975177497.Holidays-City-Breaks) ![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 # Search Holiday Rentals in Windward - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Our top choices for Windward holiday rentals ![43-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/123000000/122350000/122343000/122342907/17f3fe43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Bungalow, Ocean View | Living area | 43-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/123000000/122350000/122343000/122342907/70c06ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Bungalow, Non Smoking, Sea View | Beach/ocean view](https://images.trvl-media.com/lodging/123000000/122350000/122343000/122342907/2417ddd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/123000000/122350000/122343000/122342907/91663094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in St. Barthelemy [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Lil-Home.h122342907.Hotel-Information) £900 includes taxes & fees 25 Dec - 26 Dec [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Lil-Home.h122342907.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/100000000/99770000/99762100/99762022/5bb30dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99770000/99762100/99762022/54f96cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99770000/99762100/99762022/bc43a16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99770000/99762100/99762022/fc0fd8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in ST. JEAN [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Welcome-Aboard-Appartement-De-Luxe-A-Quelques-Pas-De-La-Plage-De-St-Jean.h99762022.Hotel-Information) 9.6/10 Exceptional (4) "Great apartment, just wished there was a balcony to enjoy the outdoors and designated parking. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Giuseppina K. £1,208 includes taxes & fees 27 Dec - 28 Dec [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Welcome-Aboard-Appartement-De-Luxe-A-Quelques-Pas-De-La-Plage-De-St-Jean.h99762022.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1598h1067x0y0-bb575516.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) ![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/w1599h1066x1y1-c7417c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Anse des Cayes [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) 9.8/10 Exceptional (6) "Wonderful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara T. £1,879 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007983/cedc2f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007983/1f3947c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007983/c509d31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007983/49a4d209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Anse des Cayes [](https://www.expedia.co.uk/St-Barthelemy-Hotels-REAL-BEACH-VILLA-ON-THE-BEACH-CLOSE-TO-FLAMANS-ST-JEAN-BEACH-CITYRESTBARS.h19007983.Hotel-Information) 9.8/10 Exceptional (84) "Great villa in an amazing location on the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve S. £2,134 includes taxes & fees 2 Jan - 3 Jan 2026 [](https://www.expedia.co.uk/St-Barthelemy-Hotels-REAL-BEACH-VILLA-ON-THE-BEACH-CLOSE-TO-FLAMANS-ST-JEAN-BEACH-CITYRESTBARS.h19007983.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.co.uk/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05®ionId=553248635975177497&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windward.d553248635975177497.Holiday-Rental-Destinations)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windward.d553248635975177497.Holiday-Rental-Destinations) ## Top Windward Hotel Reviews ![Le Barthélemy Hotel & Spa](https://images.trvl-media.com/lodging/15000000/14910000/14909600/14909517/291e5741_y.jpg) ### Le Barthélemy Hotel & Spa 10/10 Excellent "Staff-10/10 Food-10/10 Amenities-10/10 Only thing Le Barthelemy - wish they use cooling bedsheets. Or comforters - that are less warm. " [](https://expedia.co.uk/St-Barthelemy-Hotels-Le-Barthelemy-Hotel-Spa.h14909517.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’re recently stayed at Amnio’s and overall had a very pleasant experience! The room was clean, comfortable and well maintained, with all the basic amenities provided. The staff were friendly and responsive, and during breakfast service ( especially Edwidge. Thanks!). I would recommend this Hotel to travelers looking for great location and comfort." [](https://expedia.co.uk/St-Barthelemy-Hotels-Hotel-Villa-Lodge-4-Epices.h8818026.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 "Great service and communication " [](https://expedia.co.uk/St-Barthelemy-Hotels-Tropical-Hotel-St-Barth.h6956.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 "Great apartment. Good location and the views are beautiful. Really enjoyed the stay!" [](https://expedia.co.uk/St-Barthelemy-Hotels-Luxury-Apartment-Stunning-Views-5-Minutes-From-Saint-Jean-Beach-Swimming-Pool.h82811963.Hotel-Information) ![Christopher Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9481/4be4cba9_y.jpg) ### Christopher Hotel 10/10 Excellent "We love the St Christopher. It has a beautiful location and very friendly staff!! " [](https://expedia.co.uk/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 "The property was amazing and the staff were super kind and helpful. We will be back soon!" [](https://expedia.co.uk/St-Barthelemy-Hotels-La-Reserve-Des-Salines.h102896193.Hotel-Information) ![Le Toiny Hôtel & Beach Club](https://images.trvl-media.com/lodging/1000000/530000/528500/528429/372f985f_y.jpg) ### Le Toiny Hôtel & Beach Club 10/10 Excellent "Room for was " [](https://expedia.co.uk/St-Barthelemy-Hotels-Hotel-Le-Toiny.h528429.Hotel-Information) ![Rosewood Le Guanahani St Barth](https://images.trvl-media.com/lodging/60000000/59450000/59449600/59449501/6e3dd0d6_y.jpg) ### Rosewood Le Guanahani St Barth 10/10 Excellent "DID NOT GO TO SPA/ UPSET WE WERE NOT ABLE TO USE POOL ONE AFTERNOON DUE TO A CHILD WAS IN POOL WITHOUT ANY SWIM DIAPERS AND HAD AN ACCIDENT " [](https://expedia.co.uk/St-Barthelemy-Hotels-Rosewood-Le-Guanahani-St-Barth.h59449501.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 "The staff took incredible care of us! So nice to be cared for in such a personalized way. The hotel, pool, common areas, beach and guest suite were beautiful and clean. Highly recommend!!" [](https://expedia.co.uk/St-Barthelemy-Hotels-Hotel-Les-Ondines-Sur-La-Plage.h10658309.Hotel-Information) ## Find out more about Windward **Everything you need to know about** **Windward** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windward holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. **Windward holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windward. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windward holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windward holiday 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! **How to find incredible deals on Windward rentals** At Expedia, we put the best Windward holiday 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 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 holiday. 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. 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 - Popular Windward Cities - [St. Barthelemy Holiday Rentals ](https://expedia.co.uk/St-Barthelemy-Holiday-Rentals.d6140949.Travel-Guide-HolidayRentals)