Top Windward Villa Rates

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Featured Villas in Windward

Sweet Hill Villa Alba

Sweet Hill Villa Alba

saint barthelemy saint barthelemy
With a stay at this villa in St. Barthelemy, you'll be in the mountains, within a 15-minute drive of Gustavia Harbor and Lorient Beach.
Opens in a new windowSweet Hill Villa Alba
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

Anse de Marigot
With a stay at this villa in St. Barthelemy, you'll be by the ocean, within a 15-minute drive of Gustavia Harbor and Marigot Beach.
Opens in a new windowBOUGAINVILLIERS 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

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

Saint-Barthélemy St Barthélémy
With a stay at this villa in St. Barthelemy, you'll be on the beach, within a 15-minute drive of Gustavia Harbor and Lorient Beach.
Opens in a new windowVilla YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat
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Jelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room

Jelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room

SAINT BARTHELEMY
With a stay at this villa in St. Barthelemy, you'll be within a 5-minute drive of Marigot Beach and Lorient Beach.
Opens in a new windowJelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room
Wild Blue Estate (7 bedrooms)

Wild Blue Estate (7 bedrooms)

Saint Barthélemy San Bartolomé
With a stay at this villa in St. Barthelemy, you'll be within a 15-minute drive of Gustavia Harbor and Petit Cul de Sac Beach.
Opens in a new windowWild Blue Estate (7 bedrooms)
Villa Dreamtime ideal Family and Friends / 2 BDR

Villa Dreamtime ideal Family and Friends / 2 BDR

Vitet
With a stay at this villa in St. Barthelemy, you'll be by the sea, within a 15-minute drive of Gustavia Harbor and Lorient Beach.
Opens in a new windowVilla Dreamtime ideal Family and Friends / 2 BDR
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 Windward
When you stay at this villa in St. Barthelemy, you'll be on the beach, within a 5-minute drive of Petit Cul de Sac Beach and Marigot Beach.
Opens in a new windowSt Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive
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
With a stay at this villa in St. Barthelemy, you'll be within a 10-minute drive of Gustavia Harbor and Lorient Beach.
Opens in a new windowBoutique villa in les Hauts de Saint Jean with stunning Eden Rock view
Beach 2 minutes' walk, private deck, tranquility

Beach 2 minutes' walk, private deck, tranquility

SAINT-BARTHELEMY (ILE)
With a stay at this villa in St. Barthelemy, you'll be on the beach, within a 15-minute drive of Gustavia Harbor and Lorient Beach.
Opens in a new windowBeach 2 minutes' walk, private deck, tranquility
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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 Luxury Villas

It’s time to plan your next getaway, and this time, you want it to be amazing. You just want a holiday where you’ll come away with humble brags like “I just couldn’t choose between the pool or the hot tub” and “It was so hard for the whole family to pick their rooms in such a big house”. OK, maybe those aren’t so humble. And that’s exactly the point when you’ve got Windward villa accommodation from lastminute.com.au.

You know what else you might get with that villa? A gourmet kitchen. What does one do in a gourmet kitchen? Why, craft delicious meals that are bound to impress your significant other, kiddos, mum, or whoever else you count among your travelling companions. Nothing says “clan getaway” like a tasty dinner in luxey surroundings, after all. But who says you even have to cook? Conjuring up gastronomic delights takes effort, and you ask us, cheap villa holidays are all about relaxing—and enjoying the fact you’re getting so much bang for your buck. Windward has plenty of ways to delight your taste buds, and don’t get us started on the scenery. No filter, indeed.

Yes, this holiday will give you plenty of humble brags, but there’s nothing humble at all about our awesome deals. Put in for some annual leave and grab some pocket change, because we’ve got Windward villas that will have you wondering “How is that even possible?” Anything is possible—well, almost anything—when you’ve got lastminute.com.au on your side.

Windward Villas essential information

Accommodation
1024 Villas
Lowest Price
AU$3,409
Highest Price
AU$4,414
Popular accommodation
Sweet Hill Villa Alba, 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, Jelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room, Wild Blue Estate (7 bedrooms), Villa Dreamtime ideal Family and Friends / 2 BDR, St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive, Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view, Beach 2 minutes' walk, private deck, tranquility

Top trending hotels in Windward

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is AU$3,409 per night from 11 Jan to 12 Jan
AU$3,409
11 Jan - 12 Jan 2026
includes taxes & fees
Located in St. Barthelemy, Christopher Hotel is by the ocean, a 4-minute drive from Lorient Beach and 9 minutes from St. Jean Beach.
Opens in a new windowChristopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
With a stay at Tropical Hotel St Barth in St. Barthelemy, you'll be near the bay, just a 4-minute walk from St. Jean Beach and a 4-minute drive from Lorient ...
Opens in a new windowTropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
Located in St. Barthelemy, Rosewood Le Guanahani St Barth is a 2-minute drive from Grand Cul de Sac and 6 minutes from Petit Cul de Sac Beach.
Opens in a new windowRosewood Le Guanahani St Barth
Save an average of 15% on thousands of hotels when you're signed in
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is AU$4,414 per night from 26 Jan to 27 Jan
AU$4,414
26 Jan - 27 Jan 2026
includes taxes & fees
With a stay at Le Barthélemy Hotel & Spa in St. Barthelemy, you'll be within a 15-minute drive of Gustavia Harbor and Marigot Beach.
Opens in a new windowLe Barthélemy Hotel & Spa
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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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