Windward Vacation Rentals

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Top Vacation Rentals in in Windward

Enjoy unobstructed ocean views from the comfort of your room, with access to the pool area and lounge seating.

"For small groups , like family of 4 or two couples, this is a great place. Nice view, close to a number of beaches and great restaurants and at nights it has its own sense. I would recommend it highly. "

Enjoy a scenic coastal view from the comfort of this stylish living room, featuring a sofa, wicker chair, and large mirror.

"The apartment was perfect for our short trip to St. Barths. Thankfully my wife and I are in good shape because those views come with a cost: lots of stairs!! We loved our stay... the only thing that would have been nice would be pool furniture... we made the best without it though. Great apartment and would recommend it for sure!!"

Enjoy meals with a stunning view of the sea and surrounding landscape from this spacious dining area.

"Great house and team. Amazing views. House manger Francois will take care of your every need. We have been coming to the island for 25 years and one of the best acccomodations ever!"

Enjoy a serene beach experience with clear waters and a sandy shore.

Relax in a spacious living room with a sofa, wicker chair, and glass coffee table, leading to a balcony with ocean views.

Relax by the serene pool surrounded by lush tropical plants and a modern building.

"The villa was a delight! Everything we needed for an incredible stay. Perfect for our family of four- having two bathrooms was such a plus. The outside area is lush with a sumptuous plunge pool. The interior is refreshing, immaculate and well-stocked. "

Relax in this spacious living area with a high ceiling, sofa, and dining table.

"Great place. Great location. Very happy to have taken the place "

Escape to a serene tropical oasis with a charming thatched-roof structure and lush greenery.

"I thoroughly enjoyed my stay at Cats bungalow on her very private, quiet but well located enclosed property near Saline beach. The tropical setting and thoughtfully and very attractively furnished room made for a wonderful retreat after exploring and enjoying beautiful St Bart. I loved the sounds of the night which the seclusion of the property made lushly audible. My favorite beach and the city of Gustavia are only a very short but beautiful drive over a ridge offering wonderful views. Cat is...

Relax by the serene pool surrounded by lush greenery and palm trees, with a shaded gazebo and comfortable lounge seating.

"Bart has done an excellent job in preparing this little gem. Great hiking nearby and all the amenities you need. Will definitely return"

Enjoy a meal on the balcony with a view of the sea and surrounding mountains.

"Nice front Beach property "

Enjoy a refreshing swim with breathtaking ocean views from our pool area.

Relax in this serene bedroom with a large bed, dresser, and TV, surrounded by natural light and decorative touches.

"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). "

Relax by the ocean with a clear view from our pool area, surrounded by lush greenery and comfortable lounge chairs.

"Great villa and host. Property needs a little tlc but overall the stay was sublime"

Relax in the serene garden with a covered patio and lounge chairs.

"I had a wonderful stay: a modern space with great AC, a beautiful garden (you’ll probably see a turtle or two), and a lovely, helpful host. The beach is truly a 5 minute walk — an incredible amenity — and it’s location near the middle of the island made every trip a short drive."

Relax by the serene pool surrounded by lush greenery and a stunning coastal view.

"Clean, efficient to work with property manager, appliances worked well, amazing view from shared pool"

Relax in a spacious outdoor area with a deck and lounge chairs.

"The home is lovely plenty of room and space for the entire family Isabel and Stephen go above and beyond in every way, possible to make the stay memorable experience"

Relax on the oceanfront deck with a hot tub and modern sofas, taking in the breathtaking views of the sea and distant islands.

"Wonderful property right on the beach. The villa had everything we needed and the location can't be beat. There is a fantastic bakery a short walk away that we visited every day. It was the perfect spot for our family getaway."

Cozy retreat with a leaf-patterned bedspread, dark wood headboard, and a shelf for personal treasures.

"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...

Relax on the deck overlooking the sea with comfortable seating and a stunning view.

Relax in a serene outdoor space with a stone pathway, wooden bench, and dining table, surrounded by lush greenery and a clear sky.

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Top Windward Hotel Reviews

La Maison Fleur de Lune

10/10 Excellent

"This property was excellent. The staff there were absolutely superb. The host were so gracious kind & accommodating & Knowledgeable . Great cozy intimate property!! "

1 bedroom cottage located a step away from Saline Beach in St-Barth.

10/10 Excellent

"Cat's villa is exactly what we were looking for - close to Saline beach and away from the busy crowds. We enjoyed waking up early morning to make coffee in the outdoor kitchen and taking a walk along the beach. Joelle was an amazing host, assisting us with everything we needed but giving us privacy to enjoy the space. We left with fond memories and would love to return again!"

Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

10/10 Excellent

"Loved the property and property manager! Everyone was so pleasant and helpful! Was very clean and nice. Loved the experience. I will add there are a lot of steps so could see that being challenging to some. "

Find out more about Windward

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.

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Popular Windward Cities

St. Barthelemy Vacation Rentals

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Windward Vacation Rentals

Change your mind

Treat yourself

Be picky

Top Vacation Rentals in in Windward

BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

Nice 2 bed-rooms Villa at Saint Barth

Indigo cosy seaside apartment 5 mn from saint jean beach swimming pool sea view

NEW, INTIMATE BUNGALOW WITH POOL

Villa St Jean, 2 steps from Eden Rock (1 Bedroom)

One bedroom cottage located a step away from Saline beach

1 bedroom cottage located a step away from Saline Beach in St-Barth.

Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

An exceptional beachfront villa with a heated infinity pool

Appartement St Jean, Saint-barthélemy

ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

Bungalow CAZ A Saline N°2

Lovely 2 bedrooms apartment, sea view and infinity pool

Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

Villa Yvantino beachfront ( 2 bedroom )

Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente

YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN

House 2 steps from Eden Rock (3 bedrooms)

Top Windward Hotel Reviews

La Maison Fleur de Lune

Tropical Hotel St Barth

Hotel Les Ondines Sur La Plage

1 bedroom cottage located a step away from Saline Beach in St-Barth.

Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

Le Barthélemy Hotel & Spa

One bedroom cottage located a step away from Saline beach

Le Toiny Hôtel & Beach Club

Find out more about Windward

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