Windward Resorts
850.89 ft²
75 Guests
66 Bedrooms
31 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Hot Tub
CA $1,879/Night
For 7 Nights CA $13,154
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Pool
- Ocean View
CA $744/Night
For 7 Nights CA $5,208
1937.51 ft²
16 Guests
8 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
CA $1,952/Night
For 7 Nights CA $13,664
1 Bedroom
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
CA $3,167/Night
For 7 Nights CA $22,166
1399 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $937/Night
For 7 Nights CA $6,560
753.47 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $939/Night
For 7 Nights CA $6,576
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $581/Night
For 7 Nights CA $4,070
2152.78 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Pool
- Ocean View
CA $1,825/Night
For 7 Nights CA $12,772
7000 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
CA $1,507/Night
For 7 Nights CA $10,547
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $264/Night
For 7 Nights CA $1,847
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
CA $1,116/Night
For 7 Nights CA $7,815
64.58 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Pool
- Balcony/Terrace
- View
CA $361/Night
For 7 Nights CA $2,529
People Visiting Windward Also Like
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
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 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
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 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:
- 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 Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
- Villa Whalhalla-4 bed-4 bath-POINTE MILOU
- Sea view, very private
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Blue Lagoon Villa, 4 to 7 bedrooms and 1 pool
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- grand appartement, vue ocean
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.
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3500 ft²
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1507 ft²
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3229 ft²
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Ocean View
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2153 ft²
6 Guests
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CA $4,813/Night
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6 Guests
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CA $1,208/Night
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2 Guests
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1 Bathroom
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CA $343/Night
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20451 ft²
6 Guests
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Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,300/Night
For 7 Nights CA $9,102
