Best Resorts and Rentals in Windward 【 EXCLUSIVE 】Rent By Owner

Windward Resorts

Resort

Rosewood Le Guanahani St Barth

9.5

Exceptional

(2 Reviews)

31 Baths 75 Guests 850.89 ft²

R21,945/Night 7 Nights - R153,615

View Deal

Villa

Villa Whalhalla-4 bed-4 bath-POINTE MILOU

10.0

Exceptional

(36 Reviews)

4 Bedrooms 3 Baths 8 Guests 7000 ft²

R20,756/Night 7 Nights - R145,289

View Deal

Appartement Vue Mer à St-jean avec jardin privé

Apartment

Appartement Vue Mer à St-jean avec jardin privé

10.0

Exceptional

(2 Reviews)

2 Bedrooms 2 Baths 4 Guests 753.47 ft²

R10,970/Night 7 Nights - R76,791

View Deal

Highly Rated

Hotel

Hotel Les Ondines Sur La Plage

10.0

Exceptional

(87 Reviews)

1 Bath

R36,979/Night 7 Nights - R258,859

View Deal

Please Inquire Before Booking – Luxury Villa

Price Dropped

Villa

Please Inquire Before Booking – Luxury Villa

10.0

Exceptional

(1 Review)

6 Bedrooms 6 Baths 12 Guests 2691 ft²

R55,350/Night 7 Nights - R387,447

View Deal

Villa

Villa Yvantino

10.0

Exceptional

(1 Review)

8 Bedrooms 4 Baths 16 Guests 1937.51 ft²

R22,795/Night 7 Nights - R159,564

View Deal

Price Dropped

Villa

Villa Ti Rock (1 bedroom)

10.0

Exceptional

(1 Review)

1 Bedroom 4 Baths 2 Guests 1615 ft²

R22,715/Night 7 Nights - R158,998

View Deal

Villa

New ! Villa Vagabond

10.0

Exceptional

(1 Review)

3 Bedrooms 3 Baths 6 Guests 2152.78 ft²

R21,307/Night 7 Nights - R149,153

View Deal

New

Villa

Please Inquire Before Booking – Luxury Villa

10.0

Exceptional

(1 Review)

3 Bedrooms 3 Baths 6 Guests 1000 ft²

R20,287/Night 7 Nights - R142,007

View Deal

Villa

Villa La Vue - Vue panoramique sur les lagons

10.0

Exceptional

(1 Review)

4 Bedrooms 3 Baths 6 Guests 1722.23 ft²

R15,242/Night 7 Nights - R106,699

View Deal

Villa

Villa Lo d'Amour (2 bedrooms)

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 4 Guests 1615 ft²

R16,643/Night 7 Nights - R116,496

View Deal

House

Lil'Home

9.8

Exceptional

(12 Reviews)

4 Bedrooms 4 Baths 16 Guests 409.03 ft²

R12,973/Night 7 Nights - R90,807

View Deal

People Visiting Windward Also Like

More Top-Rated Resorts in Windward Area

Why Choose Rent By Owner for your Windward Resorts?

What makes our Resorts 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 Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windward

More Top-Rated Resorts in Windward Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts 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

Frequently Asked Questions About Windward Resorts

1. What are the top Resorts 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 Resorts in Windward:

2. How many Resorts are available in Windward?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windward. 