Photo by Meghan Watters

Windward Side holiday rentals

We found 13 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Windward Side to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The lush setting of Windward Side is ready to explore

The jungle, ocean views and mountains are the perfect backdrop to your holiday home in Windward Side. This scenic city attracts visitors thanks to its hiking and diving. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Exploring the natural features in Windward Side

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Windward Side. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Well's Bay Beach (1.6 mi / 2.6 km)
  • Sulfur Mine (1.2 mi / 1.9 km)
  • Cove Bay Beach (1.2 mi / 2 km)
  • Mt Scenery (0.7 mi / 1.1 km)

How to get to and around Windward Side

The nearest airport is in Saba (SAB-Juancho E. Yrausquin), located 1.3 mi (2.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Oranjestad (EUX-F.D. Roosevelt), which is 19 mi (30.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Windward Side?
The most sought-after types of holiday homes in Windward Side are villas. After something a little different? Stayz has many options to match our guests’ unique requirements, so you’ll see holiday homes in loads of shapes and sizes. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a holiday home in Windward Side?
The average price for a holiday home in Windward Side is determined by several factors, such as season, property type and length of stay. Whether you’re searching for a villa with space for extended family or a cosy cabin for just you and your sweetheart, just add your dates of travel to view stays that offer great value.
How much does it cost to rent a beach house in Windward Side?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside holiday home. Type in your Windward Side travel dates to see your options on Stayz. Can’t live without a private pool? Use our filters to pick the amenities and features you need.
Are there pet-friendly holiday homes in Windward Side?
Pack a squeezy toy and a bone for your pooch because Windward Side has six stays that throw out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates then check our “Pets allowed” filter box.
Can I rent a house with a pool in Windward Side?
Add a whole new level of fun to your trip by staying in one of the three houses with a private pool in Windward Side. Use our handy search filter to find the kind of property you want on Stayz, and then spend leisurely days splish-splashing around in a swimming pool that’s all yours.
What are popular home amenities in Windward Side?
When it comes to home amenities that guests are looking for in Windward Side, an ocean view, a water view and a chef are the most popular. With Stayz holiday homes, there are choices to fit your taste and style, whether you’re going on a trip with friends, family or even pets.
Are there large group holiday homes in Windward Side?
Take your pick of three Stayz holiday homes in Windward Side that can accommodate a group of five or more people. You’ll get all the privacy and room you need to kick back with your loved ones — and no one else.
Are there holiday homes in Windward Side that welcome kids?
Windward Side has five family-friendly holiday homes to choose from. And finding a stay that welcomes youngsters is a breeze with Stayz’s “Properties good for families” filter. On top of having the whole place to yourselves, you’ll have access to perks and amenities like multiple bedrooms, full kitchens and private pools.
What are the top attractions for families in Windward Side?
There are loads of wonderful things to see and do with the family in Windward Side, such as:

  • Cove Bay Beach
  • Wells Bay Beach
  • Dutch Museum of Saba

Can I find two-bedroom holiday homes in Windward Side?
Gather your nearest and dearest and enjoy a relaxing escape in one of the two two-bedroom holiday homes Windward Side has to offer.
Are there holiday homes with WiFi in Windward Side?
Windward Side has two holiday homes with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to scrolling social media, these Stayz homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Windward Side?
Windward Side has three holiday homes where you’ll be able to relax and recharge in air-conditioned comfort. To find a property on Stayz that offers this perk, enter your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Windward Side?
The minimum required age is usually 16, 18 or 21. It can differ from property to property on Stayz, so look at the rules of your preferred Windward Side holiday home before booking.
How long can I rent a holiday home in Windward Side for?
The length of time you can book a holiday home in Windward Side varies according to the property. Simply enter your selected dates to display a list of options offering extended stays. With many amenities like laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to get a perfect place to call your home away from home in Windward Side.

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