Windward Resorts
Resort
9.5(2 Reviews)
31 Baths
75 Guests
850.89 ft²
Private Beach
Oceanfront
Hot Tub
Spa
CA $1,887/Night
7 Nights - CA $13,209
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
CA $543/Night
7 Nights - CA $3,798
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $943/Night
7 Nights - CA $6,603
CA $3,180/Night
7 Nights - CA $22,259
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
CA $847/Night
7 Nights - CA $5,928
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $1,960/Night
7 Nights - CA $13,721
Villa
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $584/Night
7 Nights - CA $4,087
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,832/Night
7 Nights - CA $12,826
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $1,617/Night
7 Nights - CA $11,317
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,311/Night
7 Nights - CA $9,175
Villa
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
CA $1,075/Night
7 Nights - CA $7,525
Villa
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Balcony/Terrace
View
Parking
Air Conditioner
CA $1,249/Night
7 Nights - CA $8,744
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
Grand Cul-de-Sac
Barriere des Quatres Vents
Anse de Toiny
Petit Cul-de-Sac
Camaruche
Gouverneur
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
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- Blue Lagoon Villa, 4 to 7 bedrooms and 1 pool
- 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.
More Rentals You May Like Near Windward
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
CA $1,140/Night
7 Nights - CA $7,982
Apartment
9.6(19 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $363/Night
7 Nights - CA $2,540
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $2,788/Night
7 Nights - CA $19,514
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,850/Night
7 Nights - CA $33,952
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $325/Night
7 Nights - CA $2,276
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
CA $1,474/Night
7 Nights - CA $10,316
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $562/Night
7 Nights - CA $3,931
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,850/Night
7 Nights - CA $33,952
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,850/Night
7 Nights - CA $33,952
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
CA $1,217/Night
7 Nights - CA $8,518
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
CA $344/Night
7 Nights - CA $2,406
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,310/Night
7 Nights - CA $9,172
