Windward Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Holiday Rentals Destinations in Windward

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

9.2 out of 10, Wonderful, (10)
"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!!"
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

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

Lovely 2 bedrooms apartment, sea view and infinity pool

9.4 out of 10, Exceptional, (13)
"Clean, efficient to work with property manager, appliances worked well, amazing view from shared pool"
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

One bedroom cottage located a step away from Saline beach

10.0 out of 10, Exceptional, (25)
"Quiet and private property away from the hustle and bustle but walking distance to one of the great beaches on St. Barts. Great garden setting with parking and wonderful pool."
One bedroom cottage located a step away from Saline beach

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)

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.

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

10.0 out of 10, Exceptional, (49)
"Nice villa overlooking Marigot Bay. Beach is literally across the street at the base of the steep driveway. Short walk up the hill to Grand Cul de Sac with fine dining or beach cafes. Road work at the base of the hill was not an issue, in fact made it quieter. Turtle colony and cats kept us company. Very nice pool! "
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

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

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 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

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

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

We Love View, Votre Appartement à 5 Minutes de la Baie de Saint Jean

10.0 out of 10, Exceptional, (1)
"I highly recommend staying at Valerie’s apartment! It is located in St. Jean, an excellent area on the island. You’re 5 minutes from Gustavia and walking distance to the best beach clubs: Nao, Nikki, La Guerite, etc. We really enjoyed staying here because we could take our rental car around the island to different beaches and then return for the second seating at one of the beach clubs in the afternoon. You have some nice restaurants that are walking distance and if you decide to dine in Gustavi...
We Love View, Votre Appartement à 5 Minutes de la Baie de Saint Jean

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

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

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 )

Sweet Hill Villa Alba

10.0 out of 10, Exceptional, (4)
"This was an amazing property! Very clean, beautiful view, had everything we needed, good response from the host. We have no complaints! Thank you for a wonderful stay!"
Sweet Hill Villa Alba
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windward Hotel Reviews

Find out more about Windward

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.