Cottage
10.0(103 Reviews)
1 Bedroom
2 Guests
Private Pool
Oceanfront
Parking
Pool
£331/Night
7 Nights - £2,318
Windward, BL Winter Rentals & Holiday Homes
Discover winter rentals Windward - We found 1292 exact matches
- Up-front pricing
- No markup
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Compare Winter Rental in Windward
10.0
£839/Night
7 Nights - £5,874
£843/Night
7 Nights - £5,900
Villa
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
Balcony/Terrace
£562/Night
7 Nights - £3,936
£3,309/Night
7 Nights - £23,166
Villa
10.0(28 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
£611/Night
7 Nights - £4,278
£2,132/Night
7 Nights - £14,924
Villa
10.0(27 Reviews)
4 Bedrooms
9 Guests
- Private Pool
Hot Tub
Breakfast- Parking
£1,341/Night
7 Nights - £9,385
£870/Night
7 Nights - £6,089
Apartment
10.0(25 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
View
Kitchen
£199/Night
7 Nights - £1,396
Apartment
8 Bedrooms
17 Guests
- Parking
- Balcony/Terrace
- View
Air Conditioner
Unlock the Best Price
Villa
10.0(21 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£847/Night
7 Nights - £5,930
£1,040/Night
7 Nights - £7,280
Villa
10.0(16 Reviews)
7 Bedrooms
14 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£2,775/Night
7 Nights - £19,422
Villa
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
Ocean View
£765/Night
7 Nights - £5,355
Villa
10.0(11 Reviews)
1 Bedroom
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£709/Night
7 Nights - £4,960
Villa
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Breakfast
- Parking
£1,086/Night
7 Nights - £7,601
Villa
10.0(10 Reviews)
5 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
£924/Night
7 Nights - £6,470
Villa
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£735/Night
7 Nights - £5,144
Villa
10.0(9 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Hot Tub
- Breakfast
- Parking
£1,450/Night
7 Nights - £10,151
Villa
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
£1,003/Night
7 Nights - £7,018
£1,196/Night
7 Nights - £8,373
Villa
10.0(5 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£599/Night
7 Nights - £4,195
Villa
10.0(4 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£1,366/Night
7 Nights - £9,560
About Windward Winter Rental on Casai.uk
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 1292 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Frequently Asked Questions About Windward Winter Rentals
What are the top rated Winter Rentals in Windward?
There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Windward:
- Villa Costa Nova | Ocean View - Located in Stunning Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Exquisite Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Stunning Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Fabulous Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Wonderful Gouverneur with Private Pool
- Villa Kyody | Ocean View - Located in Beautiful Marigot with Private Pool
- Villa Kyody | Ocean View - Located in Magnificent Marigot with Private Pool
- VILLA LEO St jean St barthélemy
- Villa Alphane | Ocean View - Located in Beautiful Mont Jean with Private Pool
- Wine Note - Elegant Villa in St Barts - Ocean Views
How much does it cost to rent a place to stay near Windward in the wintertime?
The average cost for winter rentals in Windward is $5,108 per night. Casai has a wide list of great winter places to stay near Windward that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Windward that allow pets?
Yes, here are the top cottage/chalet rentals in Windward that allow you to bring your pet or dog:
- Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Villa Yvantino
- Tropical Hotel St Barth
- BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
See all pet-friendly vacation rentals in Windward on Casai.uk
Do you have any winter rentals in Windward that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Windward to find what works for you.
Are there winter accommodations in Windward that have indoor swimming pools?
As of 2026, the data from Casai.uk shows that there are over 1292 private swimming pools or indoor pools accommodations near Windward along with other great amenities.
Do any winter holiday rentals in Windward have hot tubs?
About 1292 holiday rentals in Windward boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Windward?
Yes, there are many luxury places to stay in Windward for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Windward with all the best amenities for your next trip.
