Discover your perfect Windward Side Vacation Rentals.
Discover Your Perfect Windward Side Vacation Homes
Best Vacation Homes in Windward Side
5.0
(6 Reviews)
- Air Conditioner
- Pool
- Private Pool
8.1
(224 Reviews)
- Pool
- View
- Ocean View
New
- Pool
- Balcony/Terrace
- Sports/Activities
|
House
8.4
(39 Reviews)
- Pool
- Balcony/Terrace
- Bedding/Linens
5.0
(2 Reviews)
- Air Conditioner
- Pool
- TV
7.6
(173 Reviews)
- Air Conditioner
- Parking
- Pool
5.0
(2 Reviews)
- Air Conditioner
- Pool
- Wheelchair Accessible
5.0
(2 Reviews)
- Air Conditioner
- Pool
- TV
Windward Side Luxury Rentals
New
- Child Friendly
5.0
(1 Review)
- Pet Friendly
- Child Friendly
4.9
(59 Reviews)
- Air Conditioner
- Balcony/Terrace
- Bedding/Linens
4.9
(9 Reviews)
- Air Conditioner
- Pool
- TV
4.7
(3 Reviews)
- Pool
- Private Pool
- Bedding/Linens
New
- Air Conditioner
- Pool
- TV
|
Resort
5.8
(11 Reviews)
- Air Conditioner
- Pool
- Balcony/Terrace
4.8
(27 Reviews)
- Pool
- TV
- Private Pool
Windward Side Pet Friendly Vacation Rentals
New
- Air Conditioner
- Pet Friendly
- Balcony/Terrace
Windward Side Top Rated Vacation Rentals
|
Hotel
8.4
(18 Reviews)
- Air Conditioner
- Pool
- Bedding/Linens
Why Choose Rent By Owner for your Windward Side Vacation Rental Homes?
What makes our Vacation Rentals 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 Side
How to Book Your Windward Side Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, youβll 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 partnerβs website.
Explore and book the perfect rental in Windward Side
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Hereβs 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 Side
Windward Side Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windward Side?
There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windward Side:
- El Momo Cottages
- Saba Arawak Hotel
- Motel β 8 guests
- El Momo Cottages
- Saba Arawak Hotel
- Queenβs hotel, bar & kitchen
- Haiku House, an amazing wooden villa situated in a tropical forest
- Caribbean Elegance & Comfort
- Modern Luxury Villa in Flatlands. Pool. Walk to Beach. Sleeps 6. Ocean Views.
- Home a way from home in the Unspoiled queen of the Caribbean.
Which vacation homes in Windward Side are best for families?
If you are looking for a family-friendly vacation home in Windward Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward Side:
How many Rentbyowner vacation rentals are available in Windward Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 22 in the Windward Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windward Side.β―