Windward Holiday Rentals

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Top Holiday Rentals Destinations in Windward

Villa in Anse de Marigot

10.0 out of 10, Exceptional, (49)
"We enjoyed staying at the villa. It was perfect for our needs."
United States
D T D.
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

Apartment in Saint Jean

9.2 out of 10, Wonderful, (12)
"The room was clean, the views spectacular!"
United States
Milton
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

Villa in saint barthelemy

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!"
United States
Haley T.
Sweet Hill Villa Alba

Holiday Home in Saline

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!"
United States
Kristina G.
One bedroom cottage located a step away from Saline beach

Villa in SAINT BARTHELEMY

10.0 out of 10, Exceptional, (7)
"Our family really enjoyed our stay at Jelo! It is a wonderful place, decorated nicely with all the amenities a family would need. Patrice is an excellent concierge. "
United States
Vesna C.
Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room

Holiday Home in Marigot

10.0 out of 10, Exceptional, (3)
"Even more beautiful than photos. Great location "
United States
Jeffrey A.
NEW, INTIMATE BUNGALOW WITH POOL

Villa in TOINY

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!"
United States
Brian M.
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

Holiday Home in Grande 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. "
United States
Russell G.
Bungalow CAZ A Saline

Apartment in St Jean

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). "
United States
Mara
Appartement St Jean, Saint-barthélemy

Apartment in Marigot

9.2 out of 10, Wonderful, (5)
"Had such an amazing experience at indigo - the host was super accommodating and helpful. She went above and beyond to make sure that everything ran super smoothly. Will absolutely be coming back and staying with them again. "
United States
Kendall M.
Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente

Holiday Home in Saint Barthelemy

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!"
United States
Manu M.
1 bedroom cottage located a step away from Saline Beach in St-Barth.

Apartment in St Jean

9.4 out of 10, Exceptional, (13)
"A wonderful spot that i would highly recommend. And the host was fantastic. "
United States
kathleen t.
Lovely 2 bedrooms apartment, sea view and infinity pool

Villa in Saint-Barthélemy

9.4 out of 10, Exceptional, (9)
"Nice front Beach property "
United States
Mariem
Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

Holiday Home in Gustavia

Nice 2 bed-rooms Villa at Saint Barth

Villa in Saint-Jean

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! "
United States
Dinara S.
Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

Apartment in St Barthélemy

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

Villa in SAINT-BARTHELEMY (ILE)

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"
France
valérie p.
Beach 2 minutes' walk, private deck, tranquility

Villa in Pointe Milou

10.0 out of 10, Exceptional, (55)
"Great villa and host. Property needs a little tlc but overall the stay was sublime"
United States
chris s.
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

Holiday Home in Grande Saline

10.0 out of 10, Exceptional, (13)
"Beautiful home and perfectly located. We loved the garden setting. We really enjoyed staying here and will be back!"
France
Alexis P.
Bungalow CAZ A Saline N°2

Villa in Saint-Barthélemy

10.0 out of 10, Exceptional, (5)
"Great location on the water."
United States
Tzvetelina P.
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

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.