Windward Resorts
Condo
10.0(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $438/Night
7 Nights - US $3,066
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
2002.09 ft²
Pool- Ocean View
- Balcony/Terrace
View
US $186/Night
7 Nights - US $1,302
Cottage
10.0(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $298/Night
7 Nights - US $2,086
Condo
10.0(102 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Pet Friendly
US $366/Night
7 Nights - US $2,564
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1711.46 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
Parking
US $284/Night
7 Nights - US $1,988
Condo
10.0(100 Reviews)
3 Bedrooms
2 Baths
6 Guests
1138 ft²
Hot Tub- Fireplace/Heating
- Pool
- Balcony/Terrace
US $246/Night
7 Nights - US $1,723
Villa
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,645
Condo
10.0(72 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $578/Night
7 Nights - US $4,048
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1636.11 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $275/Night
7 Nights - US $1,923
Condo
10.0(65 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $292/Night
7 Nights - US $2,045
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
812.67 ft²
- Balcony/Terrace
- Pet Friendly
Kitchen- Parking
US $192/Night
7 Nights - US $1,344
Condo
10.0(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
946 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $378/Night
7 Nights - US $2,646
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
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- 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.
- Island Breeze
- Not the average vacation home! Saltwater Pool & Spa electric heat incl. in rate
- Modern holiday villa overlooking the lake and the golf course
- Enchanted Private Island Oasis Steps To Beach, Tropical Yard & Charm Filled Home
- Island Beach Barn - charming vacation house with bay/dock and beach access
2. How many Resorts are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 1208 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
US $116/Night
7 Nights - US $814
House
10.0(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
1812 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $378/Night
7 Nights - US $2,646
Cottage
10.0(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $353/Night
7 Nights - US $2,472
House
10.0(32 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $208/Night
7 Nights - US $1,455
House
10.0(30 Reviews)
2 Bedrooms
2 Baths
6 Guests
1344 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $484/Night
7 Nights - US $3,388
House
10.0(28 Reviews)
2 Bedrooms
2 Baths
5 Guests
946 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $306/Night
7 Nights - US $2,144
Condo
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $317/Night
7 Nights - US $2,217
House
10.0(20 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $124/Night
7 Nights - US $870
House
10.0(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $361/Night
7 Nights - US $2,527
House
10.0(18 Reviews)
2 Bedrooms
2 Baths
8 Guests
1460 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $162/Night
7 Nights - US $1,137
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $520/Night
7 Nights - US $3,639
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $355/Night
7 Nights - US $2,486
