Vacation Rentals in Windward

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Top Vacation Rentals 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, 42 reviews
"Staying at Francois vacation home was 11/10 excellent. I spent a lot of time looking at rental options and couldn’t have been more happy with my choice. The house is a quiet getaway in the hills, with an amazing view of the ocean cove. And a great pool. It’s also spacious with two large beds, two full bathrooms, and a large living room with plenty of seating. The house is located about 15 minutes from Eden’s rock area which is home to lively beach restaurants like Nikki beach club, and about...
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.
House 2 steps from Eden Rock (3 bedrooms)
House 2 steps from Eden Rock (3 bedrooms)
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
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)
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
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
Appartement St Jean, Saint-barthélemy
10.0 out of 10, Exceptional, 1 review
"Very comfortable apartment, well-stocked kitchen. Lovely beach (St Jean) accessed via Eden Rock property several blocks away. Great price for this expensive island. L'Oasis supermarket and Le Choisy bakery (bkfst & lunch items) 1 mile away. Very busy street, lively at night, but apartment well-insulated. Parking could be challenging. Two reasonable restaurants right downstairs (Le Piment and Irish Pub). "
Appartement St Jean, Saint-barthélemy
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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.

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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 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. 


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 is more your thing. Of course, there’s always the treat of having your own 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.  


Windward Vacation Rental Travel Info

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

Recent reviews in Windward
Expedia verified reviews