Windward Holiday Rentals

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Top Holiday Rentals Destinations in Windward

1 bedroom cottage located a step away from Saline Beach in St-Barth.
9.8 out of 10, Exceptional, (22)
"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!"
1 bedroom cottage located a step away from Saline Beach in St-Barth.
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
9.2 out of 10, Wonderful, (10)
"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. "
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
9.8 out of 10, Exceptional, (52)
"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!"
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
NEW, INTIMATE BUNGALOW WITH POOL
10.0 out of 10, Exceptional, (3)
"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. "
NEW, INTIMATE BUNGALOW WITH POOL
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
10.0 out of 10, Exceptional, (55)
"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
Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
10.0 out of 10, Exceptional, (6)
"Had a great time staying in the villa. It’s pristine clean, great location and gorgeous views. If u come back to St Barth again, I’ll stay at the villa again! "
Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
10.0 out of 10, Exceptional, (49)
"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. "
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
Appartement St Jean, Saint-barthélemy
10.0 out of 10, Exceptional, (3)
"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
Indigo cosy seaside apartment 5 mn from saint jean beach swimming pool sea view
Indigo cosy seaside apartment 5 mn from saint jean beach swimming pool sea view
One bedroom cottage located a step away from Saline beach
10.0 out of 10, Exceptional, (25)
"Cat's cabin is cozy, safe and incredibly peaceful! Located super close to the amazing Saline beach! Perfect getaway on St. Barth's!"
One bedroom cottage located a step away from Saline beach
Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente
9.2 out of 10, Wonderful, (5)
"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
Bungalow CAZ A Saline
9.0 out of 10, Wonderful, (4)
"Beautiful, peaceful , cozy cottage in a great location. Only a short walk to Saline beach and 2 nearby restaurants. Cottage was perfect for a couple and immaculate. Host is great, highly recommend for St Barthes getaway. "
Bungalow CAZ A Saline
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
10.0 out of 10, Exceptional, (3)
"Great place. Great location. Very happy to have taken the place "
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
Wild Blue Estate (7 bedrooms)
10.0 out of 10, Exceptional, (1)
"This property was perfect for our group of 8 people. There was plenty of room and the villas were better than in the pictures. Jean Charles our host was perfect. He created a group chat to meet our needs and be in touch with us throughout our stay. We will definitely stay in the villas for our next trip!! Simply Outstanding!!!"
Wild Blue Estate (7 bedrooms)
Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat
9.6 out of 10, Exceptional, (8)
"Nice front Beach property "
Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat
Villa Yvantino beachfront ( 2 bedroom )
10.0 out of 10, Exceptional, (5)
"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."
Villa Yvantino beachfront ( 2 bedroom )
Beach 2 minutes' walk, private deck, tranquility
10.0 out of 10, Exceptional, (1)
"Excellent séjour Maison confortable, bien agencée avec un jardin très beauSituation impeccable proche du Monoprix et d une boulangerie Et surtout des hôtes super gentils"
Beach 2 minutes' walk, private deck, tranquility
Traditional Caribbean Style house with breathtaking views
10.0 out of 10, Exceptional, (1)
Traditional Caribbean Style house with breathtaking views
Bungalow CAZ A Saline N°2
10.0 out of 10, Exceptional, (13)
"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."
Bungalow CAZ A Saline N°2
Lovely 2 bedrooms apartment, sea view and infinity pool
9.4 out of 10, Exceptional, (13)
"A wonderful June week in not so busy St Barth. This house has a great view and is in a good location to get back to main town or out to the cul de sac beaches in short order. House had two nice rooms two baths and a very attentive manager who checked in a lot. Would be good for a family or two couples. Pool on site for use by the 10 or so apartments was great and clean and more wonderful views "
Lovely 2 bedrooms apartment, sea view and infinity pool
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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Top Windward Hotel Reviews

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, 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 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 depend 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 chosen 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.