Title: Holiday Rentals Leeward from £2,401: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Leeward Hotels](https://expedia.co.uk/Destinations-In-Leeward.d553248635975177495.Hotel-Destinations)[Leeward Car Hire](https://expedia.co.uk/Destinations-In-Leeward.d553248635975177495.Car-Hire-Destinations)[Leeward Holidays](https://expedia.co.uk/Leeward.d553248635975177495.Holidays-City-Breaks) ![Anse des Cayes featuring landscape views, general coastal views and a coastal town](https://images.trvl-media.com/place/553248635975749415/bd30699a-067f-48d5-bfe7-8ade0f817f15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635975749415/bd30699a-067f-48d5-bfe7-8ade0f817f15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Leeward holiday 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) ![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) ### Villa Vue mer Panoramique, à 5 Minute de la Plage ! [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) Anse des Cayes 9.8/10 Exceptional (10 reviews) "Wonderful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara T. £2,401 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/119000000/118070000/118061500/118061491/57c6d470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118070000/118061500/118061491/59ed2fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports court](https://images.trvl-media.com/lodging/119000000/118070000/118061500/118061491/46c244d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports court](https://images.trvl-media.com/lodging/119000000/118070000/118061500/118061491/60090b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Exclusive 5-Bed Beachfront Retreat in St. Jean [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Exclusive-5-Bed-Beachfront-Retreat-In-St-Jean.h118061491.Hotel-Information) Saint-Jean £5,684 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Exclusive-5-Bed-Beachfront-Retreat-In-St-Jean.h118061491.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/125000000/124280000/124279200/124279142/2e9d44b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/125000000/124280000/124279200/124279142/bbf26ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/125000000/124280000/124279200/124279142/3b908290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/125000000/124280000/124279200/124279142/367e70fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! Spacious Private Villa w/ Pool & Sunrise View [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Luxury-Escape-Spacious-Villa-With-Pool.h124279142.Hotel-Information) Vitet 10/10 Exceptional (1 review) £1,030 includes taxes & fees 24 Mar - 25 Mar [](https://www.expedia.co.uk/St-Barthelemy-Hotels-Luxury-Escape-Spacious-Villa-With-Pool.h124279142.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=2026-04-02&endDate=2026-04-03®ionId=553248635975177495&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Leeward%2C+St.+Barthelemy®ionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APARTMENT) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Leeward%2C+St.+Barthelemy®ionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=VILLA) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Leeward%2C+St.+Barthelemy®ionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Leeward%2C+St.+Barthelemy®ionId=553248635975177495&latLong=17.913922%2C-62.85504&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Leeward.d553248635975177495.Holiday-Rental-Destinations)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Leeward.d553248635975177495.Holiday-Rental-Destinations) ## Top Leeward Hotel Reviews ![Luxury villa with magnificent sea view](https://images.trvl-media.com/lodging/91000000/90310000/90309200/90309101/2cba3043_y.jpg) ### Luxury villa with magnificent sea view 10/10 Excellent "We are just back from another wonderful stay in this lovely villa. It's a beautifully situated place, perched just above the sea, enveloped by ocean breezes. It's also impeccably kept up and well managed (thank you Clement) and was totally comfortable for six people. This is a really warm and special place to return to each year. " [](https://expedia.co.uk/St-Barthelemy-Hotels-Luxury-Villa-Offering-A-Magnificent-Sea-View.h90309101.Hotel-Information) ![Hotel Manapany](https://images.trvl-media.com/lodging/2000000/1190000/1182300/1182278/1e7d33e0_y.jpg) ### Hotel Manapany 10/10 Excellent "365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again! " [](https://expedia.co.uk/St-Barthelemy-Hotels-Hotel-Manapany.h1182278.Hotel-Information) ![Reve de Saint Barth](https://images.trvl-media.com/lodging/89000000/88480000/88474800/88474775/w7360h4910x0y0-825faa3a_y.jpg) ### Reve de Saint Barth 10/10 Excellent "Many parking spaces to use if you rent a car which we did. The pictures are spot on for the aesthetics of the villa. Very modern which is a must for us when traveling. Indoor outdoor pool looks nice although we were out most of time so didn’t use it. Villa was very clean and had daily room cleaning " [](https://expedia.co.uk/St-Barthelemy-Hotels-REVE-DE-SAINT-BARTH.h88474775.Hotel-Information) ![Fouquet's Saint-Barth](https://images.trvl-media.com/lodging/39000000/38820000/38812000/38811961/c683c46c_y.jpg) ### Fouquet's Saint-Barth 10/10 Excellent "Amazing boutique hotel, best location. Excellent service and staff. Worth every penny!" [](https://expedia.co.uk/St-Barthelemy-Hotels-Hotel-Barriere-Le-Carl-Gustaf-St-Barth.h38811961.Hotel-Information) ![SUPERIOR WATERFRONT PRIVACY AVAILABLE MARCH AND APRIL DATES NOW](https://images.trvl-media.com/lodging/34000000/33240000/33232200/33232108/6e8a7d73_y.jpg) ### SUPERIOR WATERFRONT PRIVACY AVAILABLE MARCH AND APRIL DATES NOW 10/10 Excellent "I mean, it’s hard to describe how thrilled we were with this property…!!! It exceeded all expectations on every front!!! Byron was the perfect host, so gracious and kind and he had such patience showing us how to work his super fabulous fancy Swiss coffee maker. The pictures do not do the home justice at all!! You feel like you’re on your own private Island. You can’t see any phones or humans when you’re in this incredibly private house and the views are outrageous and the waves crashing out front have such an incredible energy and beauty and sound to them!! the breeze through the house is just magnificent and the infinity pool is perfection. There was nothing we did not love about this home!! The decor was over the top fabulous!! The beach chairs and beach towels were plentiful and fantastic and the housekeeping was superb!!! the privacy, stunning jaw-dropping views and proximity to Gustavia, st Jean and to the airport were exceptional. God willing, we will be back asap! Thank you Byron for creating such a stunning gem and for sharing it with us!! " [](https://expedia.co.uk/St-Barthelemy-Hotels-OCEAN-FRONT-PRIVATE-VILLA-ALEXI-3-MINS-WALK-TO-BEACH-5-MINS-CHECK-OUR-REVIEWS.h33232108.Hotel-Information) ![Villa Rosebud, 2BR, 2BA, Sleeps 2-4, on the beach of Anse Des Cayes](https://images.trvl-media.com/lodging/34000000/33970000/33966900/33966826/75a140b1_y.jpg) ### Villa Rosebud, 2BR, 2BA, Sleeps 2-4, on the beach of Anse Des Cayes 10/10 Excellent "Well appointed, comfortable and cozy villa close to Gustavia and shopping. Welcomed by the local property manager who helped us get settled in" [](https://expedia.co.uk/St-Barthelemy-Hotels-Villa-Rosebud.h33966826.Hotel-Information) ![Villa Vue mer Panoramique, à 5 Minute de la Plage !](https://images.trvl-media.com/lodging/94000000/93220000/93218600/93218535/4331808b_y.jpg) ### Villa Vue mer Panoramique, à 5 Minute de la Plage ! 10/10 Excellent "Morgan is amazing! He picked us up from the boat, dropped us off at the airport and make sure everything was perfect. Thank you, Morgan." [](https://expedia.co.uk/St-Barthelemy-Hotels-Villa-Vue-Mer-Panoramique.h93218535.Hotel-Information) ![Pearl Beach Hotel](https://images.trvl-media.com/lodging/1000000/60000/54000/53985/ae1c759b_y.jpg) ### Pearl Beach Hotel 6/10 Okay "Too close to Airport " [](https://expedia.co.uk/St-Barthelemy-Hotels-Pearl-Beach-Hotel.h53985.Hotel-Information) ![On the Beach, in Saint Barth... Villa Mellow Mood](https://images.trvl-media.com/lodging/75000000/74740000/74735400/74735317/40dd39a3_y.jpg) ### On the Beach, in Saint Barth... Villa Mellow Mood 10/10 Excellent "Oh my! The host, Jean, was the absolute BEST! He was so welcoming and helpful and was one of the highlights of our stay on St Barths! The home was beautiful - amazing views, comfortable beds, beautiful kitchen and living room AND a workout room and hot tub. We’d stay there again in a second. Lovely! " [](https://expedia.co.uk/St-Barthelemy-Hotels-On-The-Beach.h74735317.Hotel-Information) ## Find out more about Leeward **Everything you need to know about** **Leeward** **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 Leeward 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 Leeward holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. **Leeward holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Leeward. 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 Leeward 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 Leeward holiday rentals we have selected for you start as low as £2,401 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Leeward rentals** At Expedia, we put the best Leeward 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 Leeward 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 Leeward 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 Leeward. 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 Leeward Cities - [St. Barthelemy Holiday Rentals ](https://expedia.co.uk/St-Barthelemy-Holiday-Rentals.d6140949.Travel-Guide-HolidayRentals) ### Expedia's Latest Trends Hotels - [Beach Resorts & Hotels in Trelawny](https://expedia.co.uk/Destinations-In-Trelawny-Beach-Hotels.0-0-d6159629-tBeachHotels.Hotel-Filter-Destinations) - [All-Inclusive Hotels in Exuma](https://expedia.co.uk/Destinations-In-Exuma-All-Inclusive-Hotel.0-0-d6247365-tAllInclusiveHotel.Hotel-Filter-Destinations) - [All-Inclusive Hotels in Bonaire](https://expedia.co.uk/Destinations-In-Bonaire-All-Inclusive-Hotel.0-0-d182193-tAllInclusiveHotel.Hotel-Filter-Destinations) - [Hotels in Tortola](https://expedia.co.uk/Destinations-In-Tortola.d1116.Hotel-Destinations) - [All-Inclusive Hotels in Tobago](https://expedia.co.uk/Destinations-In-Tobago-All-Inclusive-Hotel.0-0-d602308-tAllInclusiveHotel.Hotel-Filter-Destinations) - [All-Inclusive Hotels in St. James](https://expedia.co.uk/Destinations-In-St-James-All-Inclusive-Hotel.0-0-d6050159-tAllInclusiveHotel.Hotel-Filter-Destinations) - [Luxury Hotels in Tobago](https://expedia.co.uk/Destinations-In-Tobago-Luxury-Hotel.0-0-d602308-tLuxuryHotel.Hotel-Filter-Destinations) Flights - [Flights to Tortola](https://expedia.co.uk/Destinations-In-Tortola.d1116.Flight-Destinations) - [Cheap Flights to Gustavia](https://expedia.co.uk/Cheap-Flights-To-Gustavia.d10758.Travel-Guide-Flights) - [Flights to Cat Island](https://expedia.co.uk/Destinations-In-Cat-Island.d11778.Flight-Destinations) - [Cheap Flights to Gustavia](https://expedia.co.uk/Cheap-Flights-To-Gustaf-III.d4735571.Travel-Guide-Flights) - [Flights to Bonaire](https://expedia.co.uk/Destinations-In-Bonaire.d182193.Flight-Destinations) - [Flights to Exuma](https://expedia.co.uk/Destinations-In-Exuma.d6247365.Flight-Destinations) - [Flights to Tobago](https://expedia.co.uk/Destinations-In-Tobago.d602308.Flight-Destinations) - [Flights to St. Croix Island](https://expedia.co.uk/Destinations-In-St-Croix-Island.d602171.Flight-Destinations) Activities - [Things to do in St. James](https://expedia.co.uk/Things-To-Do-In-St-James.d6050159.Travel-Guide-Activities) - [Things to do in Tortola](https://expedia.co.uk/Things-To-Do-In-Tortola.d1116.Travel-Guide-Activities) - [Things to do in Gustavia](https://expedia.co.uk/Things-To-Do-In-Gustavia.d10758.Travel-Guide-Activities) - [Things to do in Bimini Islands](https://expedia.co.uk/Things-To-Do-In-Bimini-Islands.d11777.Travel-Guide-Activities) - [Things to do in Tobago](https://expedia.co.uk/Things-To-Do-In-Tobago.d602308.Travel-Guide-Activities) Packages - [Bonaire Holidays](https://expedia.co.uk/Bonaire.d182193.Holidays-City-Breaks) - [St. Croix Island Holidays](https://expedia.co.uk/St-Croix-Island.d602171.Holidays-City-Breaks) - [Tortola Holidays](https://expedia.co.uk/Tortola.d1116.Holidays-City-Breaks) - [Exuma Holidays](https://expedia.co.uk/Exuma.d6247365.Holidays-City-Breaks) - [Bimini Islands Holidays](https://expedia.co.uk/Bimini-Islands.d11777.Holidays-City-Breaks) - [Tobago Holidays](https://expedia.co.uk/Tobago.d602308.Holidays-City-Breaks) - [Barbuda Holidays](https://expedia.co.uk/Barbuda.d506.Holidays-City-Breaks) - [Basse-Terre Island Holidays](https://expedia.co.uk/Basse-Terre-Island.d11741.Holidays-City-Breaks) Holiday Rentals - [Cayman Brac Holiday Rentals](https://expedia.co.uk/Destinations-In-Cayman-Brac.d959.Holiday-Rental-Destinations) General - [Visit Basse-Terre Island](https://expedia.co.uk/Basse-Terre-Island.dx11741)