Windward Resorts
New
House
3 Bedrooms
3 Baths
6 Guests
Oceanfront
Fireplace/Heating
Ocean View
View
CA $886/Night
7 Nights - CA $6,205
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
2002.09 ft²
Pool- Ocean View
Balcony/Terrace- View
CA $261/Night
7 Nights - CA $1,827
House
9.6(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $453/Night
7 Nights - CA $3,174
New
House
3 Bedrooms
3 Baths
6 Guests
2498 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Pet Friendly
CA $801/Night
7 Nights - CA $5,608
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1711.46 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
Parking
CA $383/Night
7 Nights - CA $2,681
New
House
3 Bedrooms
3 Baths
8 Guests
Private Pool- Pool
- Balcony/Terrace
Kitchen
CA $419/Night
7 Nights - CA $2,934
Villa
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $330/Night
7 Nights - CA $2,308
New
House
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
CA $374/Night
7 Nights - CA $2,618
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1636.11 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $385/Night
7 Nights - CA $2,698
New
House
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
CA $336/Night
7 Nights - CA $2,354
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
812.67 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
CA $269/Night
7 Nights - CA $1,886
New
House
3 Bedrooms
2 Baths
5 Guests
1700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $263/Night
7 Nights - CA $1,842
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, pool, tennis, pickleball, kayaks, SUP, dock
- Your serene escape - Modern, cozy, and close to the beach.
- Don Pedro's Cottage
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- 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.
- Not the average vacation home! Saltwater Pool & Spa electric heat incl. in rate
2. How many Resorts are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 1214 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
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
Private Beach- Oceanfront
- Ocean View
- View
CA $163/Night
7 Nights - CA $1,142
Condo
10.0(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $615/Night
7 Nights - CA $4,302
House
10.0(159 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $604/Night
7 Nights - CA $4,225
Cottage
10.0(115 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $713/Night
7 Nights - CA $4,994
Condo
10.0(102 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
CA $514/Night
7 Nights - CA $3,598
Condo
10.0(100 Reviews)
3 Bedrooms
2 Baths
6 Guests
1138 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $299/Night
7 Nights - CA $2,092
House
10.0(87 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $664/Night
7 Nights - CA $4,644
Condo
10.0(85 Reviews)
2 Bedrooms
2 Baths
6 Guests
980 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $383/Night
7 Nights - CA $2,681
Condo
10.0(69 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $685/Night
7 Nights - CA $4,793
Cabin
10.0(69 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $440/Night
7 Nights - CA $3,080
Apartment
10.0(66 Reviews)
2 Bedrooms
1 Bath
6 Guests
768 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $203/Night
7 Nights - CA $1,419
Condo
10.0(65 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $410/Night
7 Nights - CA $2,869
