Windward Vacation Rentals

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Top Vacation Rentals in in Windward

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
10.0 out of 10, Exceptional, 45 reviews
"The pictures don't do it justice! This home is spectacular and we want to come back next winter! The pool and views make this property. We also found the kitchen and bedrooms and baths to be all well appointed and very clean. The property manager and daily maid were above and beyond wonderful. Our only note for future renters is think about renting a 4 wheel drive car because the driveway is steep and our initial rear drive car skidded getting into the gate/parking but was fine after we swapped...
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
10.0 out of 10, Exceptional, 41 reviews
"The villa was perfect for our family. A tortoise family was on the property and we were greeted every day by them in the garden, my boys loved it. Nice pool and right across from the beach"
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
One bedroom cottage located a step away from Saline beach
9.8 out of 10, Exceptional, 19 reviews
"Cat's property is splendid and the bungalow is Bali chic and couldn't have been more relaxing. Saline is off the beaten path but a quick drive to almost all areas of St. Barths. We couldn't have been happier with our stay and we are already planning our return"
One bedroom cottage located a step away from Saline beach
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1 bedroom cottage located a step away from Saline Beach in St-Barth.
9.8 out of 10, Exceptional, 20 reviews
"We absolutely loved our stay at this hidden gem of a cottage!!! Loved that it was close to Saline, one of our favorite beaches on the island. Had everything we needed & the gorgeous little outdoor kitchen exceeded expectations. The pool was beautiful as well. Will definitely be back again! ❤️"
1 bedroom cottage located a step away from Saline Beach in St-Barth.
Lodge Kaz à Sucre .
10.0 out of 10, Exceptional, 3 reviews
"We had an amazing stay at the Fleur de Lune property. The villa was a wonderful mix of indoor outdoor living and our hostess and her team were very accommodating. Conveniently located near Le Tamarin, L'Esprit and Saline Beach. We would highly recommend a stay and look forward to retuning again!"
Lodge Kaz à Sucre .
Villa YVANTINO OCEAN (4 CH) or the feeling of being on the deck of a boat
10.0 out of 10, Exceptional, 2 reviews
"Thank you for a magical week in St Barth- all was exceeding expectations and as described! Can’t wait to come back and hope we can stay with you again. Merci!"
Villa YVANTINO OCEAN (4 CH) or the feeling of being on the deck of a boat
Franca Saint Jean/ 2min Walk From the Beach
10.0 out of 10, Exceptional, 1 review
"I don't think I could say enough wonderful things about our stay & the propety! Truly, Vanessa who manages the property was responsive and incredibly nice, the views are amazing, the apartment is beautiful (well decorated and tasteful and had everything you could ask for)! it is 5 minutes walking to St. Jean beach and there are lots of restaurants/bars inbetween. we loved the mix of outdoor and indoor space, the Marshall speaker, the simple and elegant bathroom, the outdoor patio besides for...
Franca Saint Jean/ 2min Walk From the Beach
Bungalow CAZ A Saline N°2
10.0 out of 10, Exceptional, 6 reviews
"Delightful bungalow steps from L’Esprit and two minute walk to Le Grain de Sel restaurants. About a five minute walk to Saline beach. Landscape is filled with wonderfully fragrant plants. Tortoises visited daily during our stay. Location was easy to find and easy to access other parts of the island. Outdoor kitchen and dining area is lovely (we appreciated the electronic mosquito swatter at dusk). Would definitely return."
Bungalow CAZ A Saline N°2
Lovely 2 bedrooms apartment, sea view and infinity pool
10.0 out of 10, Exceptional, 4 reviews
"Excellent"
Lovely 2 bedrooms apartment, sea view and infinity pool
Bungalow Oana
Bungalow Oana
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
10.0 out of 10, Exceptional, 1 review
"A+"
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms
9.4 out of 10, Exceptional, 3 reviews
"The stay is nice in the two bedroom one bath cottage attached to the owners home. The furniture, king beds, and bedding material is so comfortable and clean. TV with internet access allows vacationers to login to Netflix, Amazon Prime, etc. The kitchen is detached from the bedrooms, however, it has all the goodies to prepare almost any meal, with full size refrigerator and stove/oven and a front load LG washing machine in case clothes need to be freshened and cleaned. There were beach chairs and...
Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms
Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
10.0 out of 10, Exceptional, 38 reviews
"Beautiful villa in magnificent island, St. Barth. Ideal for a quiet relaxing get away to enjoy stunning views, clean air, nice beaches and tranquility."
Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
Villa Dreamtime ideal for Family and Friends
10.0 out of 10, Exceptional, 1 review
"The house was stunning and Sigolène made the whole process easy. The extra touches everywhere made it feel like a home away from home. It was the perfect stay for a holiday family vacation. Thank you Sigolène!!"
Villa Dreamtime ideal for Family and Friends
Welcome Aboard ! Appartement de Luxe à Quelques pas de la Plage de St Jean
10.0 out of 10, Exceptional, 3 reviews
"We ( 2 adults 1 kids) recently stayed at a wonderful place in Saint Barts that exceeded all expectations. Not only was it conveniently located near all activities, but it was impeccably clean, making for a comfortable stay. The owner's responsiveness and excellent communication made the experience even better. With plenty of restaurants nearby and access to the best beach on the island, I couldn't have asked for a better getaway. Highly recommend!"
Welcome Aboard ! Appartement de Luxe à Quelques pas de la Plage de St Jean
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
10.0 out of 10, Exceptional, 53 reviews
"Great villa and host. Property needs a little tlc but overall the stay was sublime"
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
House 2 steps from Eden Rock (3 bedrooms)
House 2 steps from Eden Rock (3 bedrooms)
Villa Moonlight .
Villa Moonlight .
Villa Yvantino beachfront
10.0 out of 10, Exceptional, 3 reviews
"Great location on the water."
Villa Yvantino beachfront
Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente
9.0 out of 10, Wonderful, 2 reviews
"The room is small but very nice with a very nice private bathroom, there’s a small kitchen and fridge, there all the equipment that you might think off, the hosts are very thoughtful and equipped the place with literally everything from towels to snorkeling equipment, there’s a car space just outside the property for guests, the hosts are very welcoming and helpful with tips on how to enjoy the island, just across the street (short walk) is a beautiful very private beach one of few where you can...
Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente
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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.

Everything you need to know about Windward 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windward vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  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!

How to find incredible deals on Windward rentals

At Expedia, we put the best Windward 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Windward Vacation Rental Travel Info

Vacation rentals
15
Popular accommodation
Windward villas
International airport
Gustavia (SBH-Gustaf III)

Recent reviews in Windward
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