Windward Winter Rental
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Pool
- Ocean View
US $537/Night
For 7 Nights US $3,762
1937.51 ft²
16 Guests
8 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
US $1,410/Night
For 7 Nights US $9,870
US $1,746/Night
For 7 Nights US $12,224
1399 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $677/Night
For 7 Nights US $4,739
5381.95 ft²
16 Guests
8 Bedrooms
7 Bathrooms
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $9,931/Night
For 7 Nights US $69,517
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $420/Night
For 7 Nights US $2,940
4305.56 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Hot Tub
- Pool
- Balcony/Terrace
US $4,432/Night
For 7 Nights US $31,024
7000 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $1,088/Night
For 7 Nights US $7,619
2152.78 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
US $2,855/Night
For 7 Nights US $19,987
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
US $806/Night
For 7 Nights US $5,645
1076.39 ft²
4 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
Villa
- Hot Tub
- Balcony/Terrace
- Breakfast
US $1,165/Night
For 7 Nights US $8,155
3500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $827/Night
For 7 Nights US $5,790
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
Barriere des Quatres Vents
Anse de Toiny
Grand Cul-de-Sac
Petit Cul-de-Sac
Gouverneur
Camaruche
Morne de Depoudre
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:
- THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Yvantino beachfront (2 bedroom)
- 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 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 Dreamtime ideal for Family and Friends
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
1036.92 ft²
22 Guests
22 Bedrooms
8 Bathrooms
Ocean View
Hotel
- Private Beach
- Oceanfront
- Spa
US $1,986/Night
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9 Guests
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4 Bathrooms
Ocean View
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- Private Pool
- Oceanfront
- Hot Tub
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2 Guests
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1 Bathroom
Ocean View
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- Ocean View
- Balcony/Terrace
- View
US $288/Night
For 7 Nights US $2,016
1507 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
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- Private Pool
- Hot Tub
- Pool
US $1,044/Night
For 7 Nights US $7,310
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $538/Night
For 7 Nights US $3,766
3229 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,477/Night
For 7 Nights US $24,338
2153 ft²
6 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,477/Night
For 7 Nights US $24,338
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
US $872/Night
For 7 Nights US $6,106
20451 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $939/Night
For 7 Nights US $6,575
1 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
US $872/Night
For 7 Nights US $6,106
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $844/Night
For 7 Nights US $5,909
1712 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
US $1,016/Night
For 7 Nights US $7,111
