Villas in Windward

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Windward villas

Outdoor pool, a heated pool

Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
Saint-Jean
10.0 out of 10, Exceptional, (10 reviews)
"Amazing Villa and best views"
Canada
Eric
Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
Outdoor dining

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

BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
Marigot
10.0 out of 10, Exceptional, (55 reviews)
"The view and pool were great!"
United States
Tom W.
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
Pool

Beautiful 4-bedroom bohemian-style villa with sea view, perfect for sunset lover

Beautiful 4-bedroom bohemian-style villa with sea view, perfect for sunset lover
Pointe Milou
Beautiful 4-bedroom bohemian-style villa with sea view, perfect for sunset lover
Exterior

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
Toiny
9.8 out of 10, Exceptional, (56 reviews)
"The house was beautiful with fabulous views!! It was clean and the beds were super comfortable. The kitchen was well equipped with everything we needed. The host was very kind and attentive. "
United States
mylene p.
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
Outdoor pool

Modern Spacious Private Villa w/ Pool & Sunrise View

Modern Spacious Private Villa w/ Pool & Sunrise View
Vitet
10.0 out of 10, Exceptional, (2 reviews)
"Great property brand new "
United Kingdom
Edoardo M.
Modern Spacious Private Villa w/ Pool & Sunrise View
An infinity pool

ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
Pointe Milou
9.8 out of 10, Exceptional, (58 reviews)
"Villa Skrutten was very nice, very clean, good sleeping arrangements, quite location, nice to have a pool, easy drives to beaches, house has everything you would need, very good location, easy walk to Christopher hotel for drinks or dinner, most importantly is that the owner Goran is extremely easy to communicate with and he is 100% on top of his game! He's likely the most quickly responsive VRBO host I've ever dealt with! "
United States
tom s.
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
Outdoor dining

Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

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

Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
Pointe Milou
10.0 out of 10, Exceptional, (26 reviews)
"I really loved Isabell she was an amazing host, she was there for us from the beginning until the end. amazing beautiful property I would come here AGAIN AND AGAIN! "
United States
Anonymous traveller
Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
Terrace/patio

Villa Yvantino beachfront ( 2 bedroom )

Villa Yvantino beachfront ( 2 bedroom )
Quartier Lorient
10.0 out of 10, Exceptional, (7 reviews)
"Great location on the water."
United States
Tzvetelina P.
Villa Yvantino beachfront ( 2 bedroom )
Outdoor dining

Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View

Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
Vitet
10.0 out of 10, Exceptional, (39 reviews)
"Villa Kali is a great spot. My husband and I stayed for just over a week. The location was fantastic, and had all the amenities. Comfortable king size bed, clean and well stocked. Everything you need to enjoy your time on the island! "
United States
Julianne N.
Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
Property grounds

THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !

THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
Grand Cul-de-Sac
10.0 out of 10, Exceptional, (10 reviews)
"Les propriétaires sont charmants, il nous répondait même tard le soir à cause du décalage horaire pour nous conseiller sur une plage ou des lieux à visiter. Et même lui dire ce que normalement les touristes n’ont pas eu l’occasion de voir , La maison est magnifique très bien équipée, très propre, rien à dire merci encore infiniment."
France
Cyril d.
THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
Terrace/patio

Villa OCEAN – Serene Oceanview Escape Near Hotel Christopher, Pointe Milou

Villa OCEAN – Serene Oceanview Escape Near Hotel Christopher, Pointe Milou
Pointe Milou
Villa OCEAN – Serene Oceanview Escape Near Hotel Christopher, Pointe Milou
Property grounds

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

Villa Rayon de Soleil | Beach Front - Located in Stunning Flamands with Concierge Services
Saint-Jean
10.0 out of 10, Exceptional, (1 review)
"La villa est impeccable et très bon service."
Canada
Pierre
Villa Rayon de Soleil | Beach Front - Located in Stunning Flamands with Concierge Services
Outdoor dining

Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room

Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room
Vitet
10.0 out of 10, Exceptional, (10 reviews)
"Absolutely gorgeous and amazing stay. Highly recommend "
United States
Sandra
Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room
Property grounds

YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN

YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN
Quartier Lorient
YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN
Pool

Villa RIVA, luxury villa, magnificent sea view, 5 min from the beach, 2 swimming pools

Villa RIVA, luxury villa, magnificent sea view, 5 min from the beach, 2 swimming pools
Marigot
10.0 out of 10, Exceptional, (1 review)
"The best place I would rent it again"
United States
nicholas d.
Villa RIVA, luxury villa, magnificent sea view, 5 min from the beach, 2 swimming pools
Outdoor dining

Villa Roy - Lagoon & Ocean Breathtaking View

Villa Roy - Lagoon & Ocean Breathtaking View
Petite Saline
10.0 out of 10, Exceptional, (12 reviews)
"We loved every moment at this beautiful Villa! What a special place. We will definitely be back! "
United States
Fume L.
Villa Roy - Lagoon & Ocean Breathtaking View
On the beach

Beach 2 minutes' walk, private deck, tranquility

Beach 2 minutes' walk, private deck, tranquility
Quartier Lorient
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location. Great amenities. "
United States
David
Beach 2 minutes' walk, private deck, tranquility
Pool

A fancy 3 bedroom property that offers a lifestyle of exceptional modern comfort

A fancy 3 bedroom property that offers a lifestyle of exceptional modern comfort
Grand Cul-de-Sac
A fancy 3 bedroom property that offers a lifestyle of exceptional modern comfort
Terrace/patio

Villa in St Jean - Spectacular view of the bay - Very private - 4 bedrooms

Villa in St Jean - Spectacular view of the bay - Very private - 4 bedrooms
Saint-Jean
10.0 out of 10, Exceptional, (2 reviews)
"This villa was an amazing stay for our family. It was spacious with a great kitchen and lots of areas to hang out together. Each bedroom was nice with a great bathroom. The pool & hot tub were a treat. Our host was responsive and super helpful when needed. Also the location was very convenient for restaurants, grocery stores, shopping & exercising. We will happily come back very soon. "
United States
Selena M.
Villa in St Jean - Spectacular view of the bay - Very private - 4 bedrooms
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

Christopher Hotel

Christopher Hotel

10/10 Excellent
"Awesome property , peaceful and beautiful views"
karl 3-night trip
Posted 5 hours ago
Christopher Hotel

Find out more about Windward

Windward Villas information

Number of reviews
283
Accommodation
723 Villas
Lowest Price
Highest Price