Holiday Rentals in Windward

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Featured Holiday Rentals in Windward

Our top choices for Windward holiday rentals

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

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

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

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

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.

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

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

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

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

Villa Rayon de Soleil | Beach Front - Located in Beautiful Flamands with Concierge Services

Villa Rayon de Soleil | Beach Front - Located in Beautiful Flamands with Concierge Services

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

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
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

Holiday Homes in Windward

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