Windward Winter Rental
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
US $386/Night
7 Nights - US $2,700
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $1,410/Night
7 Nights - US $9,870
US $816/Night
7 Nights - US $5,709
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $605/Night
7 Nights - US $4,234
US $9,931/Night
7 Nights - US $69,517
Villa
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $420/Night
7 Nights - US $2,940
US $4,432/Night
7 Nights - US $31,024
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,149/Night
7 Nights - US $8,045
Villa
4 Bedrooms
4 Baths
8 Guests
2152.78 ft²
- Oceanfront
Fireplace/Heating- Pool
- Ocean View
US $2,855/Night
7 Nights - US $19,987
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
US $811/Night
7 Nights - US $5,674
Villa
2 Bedrooms
1 Bath
4 Guests
1076.39 ft²
- Hot Tub
- Balcony/Terrace
Breakfast- Pet Friendly
US $1,165/Night
7 Nights - US $8,155
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,982/Night
7 Nights - US $13,872
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.
Explore and book the perfect rental in Windward
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
Petit Cul-de-Sac
Gouverneur
Camaruche
Morne de Depoudre
Grand Cul de Sac
Windward Winter Rental Frequently Asked Questions
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 La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Yvantino beachfront (2 bedroom)
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
- 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
2. How many Winter Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 1281 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
9.6(23 Reviews)
7 Baths
855.73 ft²
Private Beach- Oceanfront
Spa- Fireplace/Heating
US $1,400/Night
7 Nights - US $9,800
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
View- Kitchen
US $230/Night
7 Nights - US $1,609
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,048/Night
7 Nights - US $7,334
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $399/Night
7 Nights - US $2,795
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,448/Night
7 Nights - US $24,136
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,448/Night
7 Nights - US $24,136
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $865/Night
7 Nights - US $6,055
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $932/Night
7 Nights - US $6,521
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,165/Night
7 Nights - US $8,156
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $934/Night
7 Nights - US $6,539
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
1 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $865/Night
7 Nights - US $6,055
Villa
10.0(10 Reviews)
2 Bedrooms
3 Baths
4 Guests
2153 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $859/Night
7 Nights - US $6,013
