Cottage
10.0(103 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Oceanfront
Parking
Pool
AU $644/Night
7 Nights - AU $4,511
Windward Winter Rental
10.0
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
Hot Tub- Parking
Balcony/Terrace
Kitchen
AU $1,619/Night
7 Nights - AU $11,331
AU $1,171/Night
7 Nights - AU $8,198
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $867/Night
7 Nights - AU $6,067
AU $6,383/Night
7 Nights - AU $44,684
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
Skiing- Balcony/Terrace
AU $1,170/Night
7 Nights - AU $8,192
AU $4,112/Night
7 Nights - AU $28,787
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
Breakfast
AU $2,458/Night
7 Nights - AU $17,204
Villa
2 Bedrooms
1 Bath
4 Guests
1076.39 ft²
- Hot Tub
- Balcony/Terrace
Air Conditioner
Pet Friendly
AU $1,678/Night
7 Nights - AU $11,746
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Parking
Ocean View- Balcony/Terrace
View
AU $367/Night
7 Nights - AU $2,568
Apartment
10 Bedrooms
10 Baths
21 Guests
896.99 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
AU $2,006/Night
7 Nights - AU $14,041
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,597/Night
7 Nights - AU $11,181
Why Choose Rent By Owner for your Windward Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward
How to Book Your Windward Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward
Quartier Lorient
Morne Criquet
Pointe Milou
Grand Cul-de-Sac
Anse de Toiny
Barriere des Quatres Vents
Gouverneur
Camaruche
Petit Cul-de-Sac
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Winter Rentals
1. What are the top 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
2. How many Winter Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 1284 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Windward.
More Rentals You May Like Near Windward
Hotel
9.7(22 Reviews)
7 Baths
855.73 ft²
Private Beach- Oceanfront
- Breakfast
EV Charge Station
AU $1,996/Night
7 Nights - AU $13,971
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Breakfast
- Parking
- Pool
AU $1,557/Night
7 Nights - AU $10,902
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Parking
- Pool
- Ocean View
AU $1,478/Night
7 Nights - AU $10,349
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,387/Night
7 Nights - AU $9,709
Villa
10.0(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
1981 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
AU $1,927/Night
7 Nights - AU $13,486
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $1,750/Night
7 Nights - AU $12,253
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $1,329/Night
7 Nights - AU $9,301
Villa
10.0(9 Reviews)
3 Bedrooms
3 Baths
7 Guests
2153 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
AU $2,710/Night
7 Nights - AU $18,967
Villa
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
AU $1,856/Night
7 Nights - AU $12,993
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1561 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $1,826/Night
7 Nights - AU $12,778
Villa
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
AU $1,142/Night
7 Nights - AU $7,994
Villa
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $1,608/Night
7 Nights - AU $11,257
