A red boat on a sandy beach with a rocky hill in the background.

Villas in Windward

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windward villas

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, (27 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
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, (57 reviews)
"Always an amazing stay here at ROC e Mar! We look forward to our next trip! "
United States
Fume L.
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
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
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
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)
"Fantastic property and responsive host! We really enjoyed the week-long trip and would absolutely recommend."
United States
Chris H.
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING
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
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
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, (3 reviews)
"Great property brand new "
United Kingdom
Edoardo M.
Modern Spacious Private Villa w/ Pool & Sunrise View
Terrace/patio

Villa Yvantino beachfront ( 2 bedroom )

Villa Yvantino beachfront ( 2 bedroom )
Quartier Lorient
10.0 out of 10, Exceptional, (8 reviews)
"Great location on the water."
United States
Tzvetelina P.
Villa Yvantino beachfront ( 2 bedroom )
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)
"We really enjoyed our stay. It was a wonderful property. I would recommend to others as well. Theo the concierge is the best. Help us whenever we needed. Thank you for a wonderful space to start our vacation! "
United States
Michael G.
THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
Pool

ROYAL PALM by WIMCO St. Barth Properties

ROYAL PALM by WIMCO St. Barth Properties
Vitet
ROYAL PALM by WIMCO St. Barth Properties
Property grounds

YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN

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

SUNRISE - LUXURY VILLA AT THE HEART OF THE ISLAND

SUNRISE - LUXURY VILLA AT THE HEART OF THE ISLAND
Saint-Jean
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at Villa Sunrise! From the moment we booked, our host Peggy reached right out to us and making us feel welcomed. She was very communicative and provided helpful info about the villa and surrounding area. The views from this villa cannot be beat! We loved having so much outdoor space. The bedrooms were comfortable and cozy as well. Even though we were high up we enjoyed being able to walk down to the beach clubs in Saint Jean during the afternoon and had a taxi to drive us...
United States
Vanessa A.
SUNRISE - LUXURY VILLA AT THE HEART OF THE ISLAND
Exterior

Modern villa, a 3-minute walk from St. Jean Beach, shops, and restaurants.

Modern villa, a 3-minute walk from St. Jean Beach, shops, and restaurants.
Saint-Jean
8.6 out of 10, Excellent, (7 reviews)
"The home was as advertised, looks like it was just updated. Great location so not to spend your trip driving around the island.Happy with all aspects and look forward to staying agin in July. "
United States
Michael D.
Modern villa, a 3-minute walk from St. Jean Beach, shops, and restaurants.
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
Exterior

C'EST MA VUE by WIMCO St. Barth Properties

C'EST MA VUE by WIMCO St. Barth Properties
Saint-Jean
C'EST MA VUE by WIMCO St. Barth Properties
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
Terrace/patio

NEW! Villa Vagabond Breathtaking Panoramic View & Caribbean Charm St-Barts 3 Bdr

NEW! Villa Vagabond Breathtaking Panoramic View & Caribbean Charm St-Barts 3 Bdr
Petite Saline
NEW! Villa Vagabond Breathtaking Panoramic View & Caribbean Charm St-Barts 3 Bdr
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
Terrace/patio

Villa LAGON JAUNE – Twin Villa Estate with 7 Bedrooms & Ocean Views in Petit Cul de Sac, St. Barths

Villa LAGON JAUNE – Twin Villa Estate with 7 Bedrooms & Ocean Views in Petit Cul de Sac, St. Barths
Saint-Jean
Villa LAGON JAUNE – Twin Villa Estate with 7 Bedrooms & Ocean Views in Petit Cul de Sac, St. Barths
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
"The hotel is amazing along with the staff they cover everything you need for the trip from room and hotel service to reservations A Must stay"
vincent 6-night trip
Posted 1 day ago
Christopher Hotel

Find out more about Windward

Windward Villas information

Number of reviews
232
Accommodation
693 Villas
Lowest Price
Highest Price