Photo by Meghan Watters

Windward Side vacation rentals

We found 12 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Windward Side to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

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, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Windward Side

Find out more about Windward Side

The lush setting of Windward Side is ready to explore

The jungle, ocean views and mountains are a perfect backdrop to your vacation home in Windward Side. This scenic city allures visitors with its hiking and diving. A vacation 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 an active traveler or just want to take in the scenery, Windward Side is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Well's Bay Beach (1.6 mi / 2.6 km)
  • Mt Scenery (0.7 mi / 1.1 km)
  • Cove Bay Beach (1.2 mi / 2 km)
  • Sulfur Mine (1.2 mi / 1.9 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 center. If you can't find a flight that works for your travel itinerary, you might consider flying into Oranjestad (EUX-F.D. Roosevelt), which is 19 mi (30.5 km) away.

Frequently asked questions

What is the best area to stay in Windward Side when booking a vacation rental?
When planning a vacation rental in Windward Side, Saba, one of the most charming areas to consider is the heart of the village itself. This picturesque neighbourhood offers a delightful blend of local culture and stunning natural beauty. Staying here puts you within easy reach of the iconic Mount Scenery, which is a must-visit for hiking enthusiasts, as it boasts the highest point in the Dutch Caribbean and provides breathtaking views of the surrounding islands. Additionally, the charming Windward Side features quaint local shops, restaurants, and the vibrant community atmosphere, making it an ideal base for your adventures.

In terms of vacation rentals, Windward Side has a selection of properties that cater to various preferences, from cosy cottages to more spacious villas. The area is not overly saturated with rentals, ensuring a more personalised experience for guests while still providing enough options to find something that suits your needs.
How much does it cost to rent a vacation home in Windward Side?
Prices for vacation rentals in Windward Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windward Side to more spacious homes.
Are there any discounts for Windward Side vacation house rentals?
You can find great discounts on house rentals in Windward Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Windward Side?
For renting a beach house in Windward Side, Saba, travellers should explore the southern coast of the island, particularly around the scenic beaches near Well's Bay and the picturesque Ladder Bay. These areas provide a range of vacation rentals, often featuring stunning views of the Caribbean Sea and the surrounding lush landscapes. Many properties in this region come with amenities such as private balconies, outdoor dining areas, and well-equipped kitchens, ideal for those seeking a relaxed beachside experience.

Ladder Bay, known for its serene atmosphere and easy access to pristine waters, offers villas and cottages that frequently include private pools or direct beach access. Additionally, properties in this area often feature amenities like air conditioning, Wi-Fi, and outdoor showers, suiting the needs of beachgoers and nature lovers alike.

The nearby area around Well's Bay is also worth considering, where you can find charming beach houses located among the greenery. Many of these accommodations are designed for comfort and relaxation, with spacious living areas, hammocks for lounging, and proximity to local dive sites, making them great for those interested in water sports.
What is the most popular type of vacation rental accomodation in Windward Side?
In Windward Side, cottages, villas, and vacation houses are all popular types of vacation rentals, with several options available in this charming area. These accommodations often feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where guests can relax and enjoy the stunning views of the surrounding landscape. Many properties are designed to provide a comfortable home-away-from-home experience, making them ideal for families or groups looking to explore the natural beauty of Saba.
Are there any family house rentals in Windward Side?
In Windward Side, Saba, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This picturesque area is renowned for its stunning natural beauty and offers easy access to attractions such as the Saba National Marine Park, great for family outings.

Accommodations typically provide spacious living areas that cater to larger groups, along with fully equipped kitchens for preparing meals together. Many properties also feature outdoor spaces where children can play, and some even come with private terraces that offer breathtaking views of the surrounding landscape.
Can I rent a vacation home with a pool or hot tub in Windward Side?
In Windward Side, Saba, there are several vacation homes available for rent that come equipped with pools or hot tubs, offering a great retreat for those seeking relaxation amidst stunning natural surroundings. This charming area is known for its lush landscapes and scenic views, making it an idyllic destination for a getaway.
Can I find long-stay vacation rentals in Windward Side?
A long-stay vacation rental in Windward Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Windward Side?
In Windward Side, Saba, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these vacation homes offer stunning views of the surrounding landscapes and the Caribbean Sea, ensuring a picturesque stay. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor terraces superb for enjoying the tropical climate.
Are there any remote work vacation rentals in Windward Side?
In Windward Side, Saba, there are several remote work vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with essential amenities for remote work, including Wi-Fi, desk chairs, and even computer monitors, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windward Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windward Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windward Side?
In Windward Side, popular vacation rental amenities include kitchens equipped with essential cookware, dishware, and utensils, allowing guests to prepare their own meals. Additionally, many rooms feature microwaves and coffee-making facilities, making it convenient for travellers to enjoy a quick breakfast or snack.
When is the best time to visit Windward Side for a vacation rental?
April is one of the most popular months to visit the Windward Side of Saba, thanks to its stunning landscapes and vibrant marine life. The peak season runs from March to May, drawing travellers seeking a blend of relaxation and adventure. During this time, outdoor activities such as hiking the lush trails of Mount Scenery and diving in the crystal-clear waters become the highlight of your stay. The comfortable temperatures, generally ranging from 24 to 30 degrees Celsius, make it superb for exploring the island's natural beauty.

For those who prefer a quieter experience, consider planning your visit in October. While this month falls into the low season, it offers a unique charm as the island is less crowded, allowing for intimate encounters with the local wildlife and peaceful exploration of the picturesque villages. You can enjoy the warm sea for swimming and snorkelling without the hustle and bustle of peak tourist activity.
How early should I book a Windward Side vacation rental?
Book your Windward Side vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Windward Side home rental booking on Vrbo?
To find Windward Side vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Windward Side vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Vacation Rentals ideas

Bognor Regis Vacation Rentals
Standard Link for Bognor Regis
The Riverwood Conservancy Vacation Rentals
Standard Link for The Riverwood Conservancy
Myers Point Vacation Rentals
Standard Link for Myers Point
Sun Valley Ski Resort Vacation Rentals
Standard Link for Sun Valley Ski Resort
Humber Bay Shores Vacation Rentals
Standard Link for Humber Bay Shores
Kralendijk Vacation Rentals
Standard Link for Kralendijk
Posillipo Vacation Rentals
Standard Link for Posillipo
Limerick Vacation Rentals
Standard Link for Limerick
Bradwell Vacation Rentals
Standard Link for Bradwell
Piazza San Pietro Caveoso Vacation Rentals
Standard Link for Piazza San Pietro Caveoso
Dunham Vacation Rentals
Standard Link for Dunham
La Perla Vacation Rentals
Standard Link for La Perla
Schwarzbach Vacation Rentals
Standard Link for Schwarzbach
Sveti Kriz Zacretje Vacation Rentals
Standard Link for Sveti Kriz Zacretje
Wack-Wack Greenhills Vacation Rentals
Standard Link for Wack-Wack Greenhills
Algonquin Park Vacation Rentals
Standard Link for Algonquin Park
Lake Panorama Vacation Rentals
Standard Link for Lake Panorama
Duvall Vacation Rentals
Standard Link for Duvall
Kopan Monastery Vacation Rentals
Standard Link for Kopan Monastery
Playa Nacascolo Vacation Rentals
Standard Link for Playa Nacascolo
Verbier Ski Resort Vacation Rentals
Standard Link for Verbier Ski Resort
Sunset Beach Resort Au Natural Beach Vacation Rentals
Standard Link for Sunset Beach Resort Au Natural Beach
Lily Lake Vacation Rentals
Standard Link for Lily Lake
Arborg Vacation Rentals
Standard Link for Arborg
Monterra Resort Vacation Rentals
Standard Link for Monterra Resort

People also search for

St. John's Cottages
Standard Link for St. John's
Lagos Villas
Standard Link for Lagos
Gatlinburg Chalets
Standard Link for Gatlinburg
Sarasota Villas
Standard Link for Sarasota
Costa Rica Villas
Standard Link for Costa Rica