Windward Beach Home Rentals
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Pool
- Ocean View
US $537/Night
For 7 Nights US $3,762
753.47 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $679/Night
For 7 Nights US $4,750
US $2,287/Night
For 7 Nights US $16,012
3229 ft²
10 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $5,795/Night
For 7 Nights US $40,563
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
3000 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
US $2,411/Night
For 7 Nights US $16,874
2152.78 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Pool
- Ocean View
US $1,318/Night
For 7 Nights US $9,226
807 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- Balcony/Terrace
- View
US $288/Night
For 7 Nights US $2,016
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $191/Night
For 7 Nights US $1,334
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $538/Night
For 7 Nights US $3,766
850.89 ft²
75 Guests
31 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $1,357/Night
For 7 Nights US $9,502
2153 ft²
6 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,508/Night
For 7 Nights US $24,557
Why Choose Rent By Owner for your Windward Beach Home Rentals?
What makes our Beach Home Rentals 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 Beach Home Rentals
What's our booking process?
Our platform allows you to browse a curated selection of beach home rentals. 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 Beach Home Rentals Amenities
What amenities can you expect?
Our Beach Home Rentals 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
Windward Beach Home Rentals Frequently Asked Questions
1. What are the top Beach 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 Beach Rentals in Windward:
- Villa Yvantino beachfront (2 bedroom)
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- Villa Paradise .
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
- Villa Case et Cuisine (2 bedrooms)
- 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 Beach Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 2190 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Beach Rentals in Windward.
More Rentals You May Like Near Windward
1453.13 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
US $489/Night
For 7 Nights US $3,423
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
20451 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $939/Night
For 7 Nights US $6,575
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $2,464/Night
For 7 Nights US $17,251
2150 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $1,440/Night
For 7 Nights US $10,081
1 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
US $880/Night
For 7 Nights US $6,161
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
3767 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $1,444/Night
For 7 Nights US $10,105
2153 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
US $1,831/Night
For 7 Nights US $12,818
1615 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
US $885/Night
For 7 Nights US $6,197
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,287/Night
For 7 Nights US $23,007
