Vacation Rentals in Windward

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Top Vacation Rentals in Windward

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

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

9.8 out of 10, Exceptional, (22)
"Bart has done an excellent job in preparing this little gem. Great hiking nearby and all the amenities you need. Will definitely return"
1 bedroom cottage located a step away from Saline Beach in St-Barth.

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 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

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

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

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

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)

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

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

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

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

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

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

Nice 2 bed-rooms Villa at Saint Barth

Nice 2 bed-rooms Villa at Saint Barth

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 )
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

Find out more about Windward

Discover your perfect Windward vacation rental with Expedia

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.  


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Explore a world of travel with Expedia