Windward Luxury Rental
Villa
5 Bedrooms
4 Baths
10 Guests
Private Pool
Oceanfront
Hot Tub
Parking
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Villa
6 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
Pool
Ocean View
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Villa
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Villa
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Villa
5 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Villa
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Villa
6 Bedrooms
3 Baths
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Why Choose Rent By Owner for your Windward Luxury Rental?
What makes our Luxury 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 Luxury Rental
What's our booking process?
Our platform allows you to browse a curated selection of luxury 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 Luxury Rental Amenities
What amenities can you expect?
Our Luxury 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
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Luxury Rentals
1. What are the top Luxury 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 Luxury Rentals in Windward:
- Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Hotel Les Ondines Sur La Plage
- BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
- Villa Whalhalla-4 bed-4 bath-POINTE MILOU
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- grand appartement, vue ocean
- Amazing swimming pool. La Roche dans l'Eau.
- Lagon Jaune, amazing sea view, direct owner, credit card, 3 or 4 bedrooms rate
- Bungalow CAZ A Saline N°2
2. How many Luxury Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3594 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Luxury Rentals in Windward.
More Rentals You May Like Near Windward
Villa
10 Bedrooms
10 Baths
20 Guests
13455 ft²
- Private Pool
- Parking
- Pool
Balcony/Terrace
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7 Bedrooms
4 Baths
14 Guests
- Private Pool
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3 Bedrooms
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7 Bedrooms
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3 Bedrooms
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6 Guests
- Private Pool
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5 Bedrooms
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10 Guests
- Private Pool
- Oceanfront
- Parking
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Villa
4 Bedrooms
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8 Guests
- Private Pool
- Oceanfront
- Parking
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New
Villa
6 Bedrooms
6 Baths
12 Guests
17000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
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Villa
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
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Villa
9 Bedrooms
9 Baths
20 Guests
Child Friendly
Security/Safety
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