Book Holiday Homes in Windward

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Featured Holiday Homes in Windward

Bungalow CAZ A Saline N°2

Bungalow CAZ A Saline N°2

SAINT-BARTHELEMY
Stay at this vacation home in St. Barthelemy. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Gustavia Harbor and Saline Beach are located ...
Bungalow CAZ A Saline N°2
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)

Villa St Jean, 2 steps from Eden Rock (1 Bedroom)

Saint-Barthélemy
Stay at this vacation home in St. Barthelemy. Enjoy a fitness center, a garden, and patios. Popular attractions Gustavia Harbor and St. Jean Beach are located ...
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
NEW - NEW BUNGALOW, POINTE MILOU

NEW - NEW BUNGALOW, POINTE MILOU

saint barthelemy
The price is NZ$1,194 per night from 3 Jan to 4 Jan
NZ$1,194
includes taxes & fees
3 Jan - 4 Jan 2025
Stay at this vacation home in St. Barthelemy. Enjoy air conditioning. Popular attractions Gustavia Harbor and Marigot Beach are located nearby.
NEW - NEW BUNGALOW, POINTE MILOU
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One bedroom cottage located a step away from Saline beach

One bedroom cottage located a step away from Saline beach

Saline
Stay at this vacation home in St. Barthelemy. Enjoy free WiFi, private pools, and a garden. Popular attractions Gustavia Harbor and Saline Beach are located ...
One bedroom cottage located a step away from Saline beach
1 bedroom cottage located a step away from Saline Beach in St-Barth.

1 bedroom cottage located a step away from Saline Beach in St-Barth.

Saint Barthelemy
Stay at this vacation home in St. Barthelemy. Enjoy free WiFi, private pools, and a garden. Popular attractions Gustavia Harbor and Saline Beach are located ...
1 bedroom cottage located a step away from Saline Beach in St-Barth.
Lodge Kaz à Sucre  .

Lodge Kaz à Sucre .

La Grande Saline
Stay at this vacation home in St. Barthelemy. Enjoy free breakfast, an in-room coffeemaker, and air conditioning. Popular attractions Gustavia Harbor and Saline ...
Lodge Kaz à Sucre .
Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms

Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms

Saint Barthelemy
The price is NZ$1,629 per night from 6 Jan to 7 Jan
NZ$1,629
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this vacation home in St. Barthelemy. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Gustavia Harbor and Grand Cul de Sac are located ...
Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms
House 2 steps from Eden Rock (3 bedrooms)

House 2 steps from Eden Rock (3 bedrooms)

Saint-Barthélemy
Stay at this vacation home in St. Barthelemy. Enjoy a fitness center, a garden, and patios. Popular attractions Gustavia Harbor and St. Jean Beach are located ...
House 2 steps from Eden Rock (3 bedrooms)
Bungalow CAZ A Saline

Bungalow CAZ A Saline

Saint-Barthélemy
Stay at this vacation home in St. Barthelemy. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Gustavia Harbor and Saline Beach are ...
Bungalow CAZ A Saline
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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.

Windward Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windward vacation homes are the perfect way for you to wing it.

Holiday houses in Windward let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windward in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windward adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windward with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windward vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windward Holiday Homes essential information

Accommodation
28 Holiday Homes
Lowest Price
NZ$1,194
Highest Price
NZ$4,730
Popular accommodation
Bungalow CAZ A Saline N°2, Villa St Jean, 2 steps from Eden Rock (1 Bedroom), NEW - NEW BUNGALOW, POINTE MILOU , One bedroom cottage located a step away from Saline beach, 1 bedroom cottage located a step away from Saline Beach in St-Barth., Lodge Kaz à Sucre ., Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms, House 2 steps from Eden Rock (3 bedrooms), Bungalow CAZ A Saline

Top trending hotels in Windward

Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac ...
Rosewood Le Guanahani St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is NZ$2,405 per night from 12 Jan to 13 Jan
NZ$2,405
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac, St. Barthelemy
The price is NZ$4,730 per night from 14 Jan to 15 Jan
NZ$4,730
includes taxes & fees
14 Jan - 15 Jan 2025
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Grand Cul ...
Le Barthélemy Hotel & Spa
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Tropical Hotel St Barth

Tropical Hotel St Barth

Baie de St. Jean, St. Barthelemy
The price is NZ$2,973 per night from 24 Dec to 25 Dec
NZ$2,973
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this beach hotel in St. Barthelemy. Enjoy free WiFi, free valet parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
Tropical Hotel St Barth
Don't see what you're looking for?
See all available properties in Windward
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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.

More ways to explore Windward

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