Windward Resorts
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R6,391/Night
For 7 Nights R44,739
2002.09 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Pool
- Ocean View
- Balcony/Terrace
R3,035/Night
For 7 Nights R21,244
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
R4,862/Night
For 7 Nights R34,036
2000 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R12,208/Night
For 7 Nights R85,448
1711.46 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Pool
- Pet Friendly
- Parking
R4,453/Night
For 7 Nights R31,180
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R12,043/Night
For 7 Nights R84,306
1345.49 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
R3,834/Night
For 7 Nights R26,840
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Fireplace/Heating
- Air Conditioner
- Internet
R8,619/Night
For 7 Nights R60,337
1496.18 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Air Conditioner
R8,468/Night
For 7 Nights R59,277
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
R7,294/Night
For 7 Nights R51,053
1636.11 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Pool
R3,859/Night
For 7 Nights R27,020
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R4,296/Night
For 7 Nights R30,071
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
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:
- Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
- Waterfront, Gulf view ,1 pet, tennis/pickleball Pool is closed at this time
- Waterside 2BR lagoon retreat. Beach, dock, pool, dog-friendly. Incommunicado!
- Your serene escape - Modern, cozy, and close to the beach.
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- Don Pedro's Cottage
- 3 bed/3 bath with Stunning Lakeview from private pool
- Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
- Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo!
- Cloud 9 on LGI Beach! No Roads. No Cars. Just Island Life w/Beach to Bay Views.
2. How many Resorts are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 1172 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
812.67 ft²
10 Guests
3 Bedrooms
2 Bathrooms
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,133/Night
For 7 Nights R21,929
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R2,782/Night
For 7 Nights R19,482
1350 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,424/Night
For 7 Nights R51,967
1150 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,584/Night
For 7 Nights R53,093
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,132/Night
For 7 Nights R56,927
980 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R5,071/Night
For 7 Nights R35,504
1138 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R3,959/Night
For 7 Nights R27,721
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,231/Night
For 7 Nights R50,613
980 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R4,950/Night
For 7 Nights R34,656
1500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,071/Night
For 7 Nights R56,503
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,610/Night
For 7 Nights R39,273
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R4,766/Night
For 7 Nights R33,367
