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Windward Side vacation rentals

We found 8 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.

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Find out more about Windward Side

Why visit Windward Side

  • Breathtaking scenery: Windward Side features stunning coastal views and lush landscapes, perfect for nature lovers.
  • Cultural attractions: Visit the Saba Museum and historic Saban cottages to immerse yourself in local heritage.
  • Outdoor adventures: Enjoy activities like snorkeling and diving in the unique waters surrounding Saba.
  • Charming accommodations: Choose from luxurious villas, cozy cottages, or modern apartments for a perfect stay.
  • Relaxing atmosphere: Experience the tranquil vibe of Windward Side, ideal for a romantic getaway or peaceful retreat.

Popular types of accommodation in Windward Side

Explore the charm of Windward Side with a variety of vacation rentals, including stunning villas, cozy cottages, and modern apartments. Whether you’re seeking a luxurious retreat with the best amenities or a quaint Saba cottage with an outdoor terrace and free Wi-Fi, you’ll find the perfect spot for your getaway. Discover the ideal accommodation for your trip and enjoy all that this beautiful destination has to offer.

  • Villas: The top choice for vacationers in Windward Side, these spacious and luxurious homes offer stunning views and private amenities.
  • Cottages: A close second, these quaint and charming abodes provide a cozy atmosphere, perfect for a romantic getaway or family retreat.
  • Apartments: Ideal for those seeking convenience, these modern rentals offer comfortable living spaces and easy access to local attractions.
  • Houses: A popular option for groups, these homes offer a home-like experience with plenty of space for relaxation and fun.**

Top attractions in and around Windward Side

Windward Side offers a perfect blend of beach, outdoor adventures, and stunning scenery for your vacation. Explore local attractions like the Saba Museum, historic Saban cottages, and enjoy breathtaking aerial views. Whether you're seeking culture, history, or adventure, this charming area caters to all types of travelers. Don't miss the chance to immerse yourself in the rich heritage of Saba while enjoying its beautiful landscapes.

  • Mt Scenery: Rising 2,877 feet, Mt Scenery offers breathtaking views and a rewarding hiking experience. Surrounded by lush greenery, it's perfect for adventure seekers and nature lovers alike.
  • Dutch Museum of Saba: Located in Windward Side, this museum showcases Saba's rich history and culture through engaging exhibits, artifacts, and local stories, providing insight into island life.
  • Jo Bean Glass Art Studio: Step into creativity at Jo Bean Glass Art Studio, where you can admire and purchase stunning glass art pieces. This gallery reflects the vibrant local culture and artistry.

Things to do recommended for couples

Windward Side offers couples breathtaking sunsets at Flat Point, intimate dinners at local seafood restaurants, and cozy hikes in the lush rainforest. Don't miss a scenic drive along the coast or enjoying a couple's massage at a charming spa for a truly memorable getaway.

Things to do recommended for families

In Windward Side, families can explore the lush hiking trails of Mount Scenery, snorkel in the crystal-clear waters at The Bottom, or enjoy local cuisine at family-friendly eateries. Saba's charming villages and friendly atmosphere make it a perfect destination for kids and parents alike.

Things to do recommended for groups

Explore the charming Windward Side village with its colorful houses, hike to the stunning Mount Scenery, and enjoy a group snorkeling tour at the nearby reefs. In Bonaire, dive together at the famous dive sites, and on Sint Eustatius, visit the historic Fort Oranje for breathtaking views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windward Side

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Windward Side with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily narrow down your options on Vrbo to find exactly what you need and more.
  • Traveling to Windward Side with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windward Side: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Windward Side: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Windward Side

Windward Side, Saba, is a paradise for those seeking breathtaking scenery and outdoor adventures. Explore the stunning Saba coastline, where pristine beaches meet lush landscapes. Enjoy amazing views from various vantage points and immerse yourself in the relaxing atmosphere of this charming city. Don't miss the opportunity to discover the unique waters around Saba, perfect for snorkeling and diving. Whether you're looking for a romantic getaway or a luxury vacation home, Windward Side has something for everyone.

  • Oranjestad: Oranjestad is a vibrant city located 19 miles from Windward Side, known for its stunning outdoor experiences and picturesque beaches. Travelers flock to this destination for its scenic views and recreational activities. Popular venues include luxurious resorts and well-maintained golf courses that cater to both relaxation and adventure seekers. While in Oranjestad, don’t miss the local history museum, which offers insights into the region's rich culture, or take a leisurely stroll along the beach and bay, soaking up the sun and enjoying the beautiful surroundings.
  • The Bottom: Situated just 1 mile from Windward Side, The Bottom is a charming city rich in culture and outdoor activities. It’s an excellent spot for those looking to immerse themselves in local traditions while enjoying the beach and mountainous landscapes. Visitors can enjoy hiking trails that lead to breathtaking views and explore nearby golf courses. Attractions like the beach and history museum provide a perfect blend of relaxation and education, making The Bottom a must-visit for a culturally themed vacation.
  • Upper Zion's Hill: Upper Zion's Hill is a quaint village nestled in the area surrounding Windward Side, offering a unique beach experience. Known for its beautiful coastline, it features a popular nudist beach that attracts sun-seekers and beach lovers alike. The tranquil atmosphere and stunning views make it an ideal getaway for those looking to unwind by the sea. With its close proximity to Windward Side, Upper Zion's Hill is a perfect spot for a leisurely day in the sun, enjoying the natural beauty of the island.

Best time to go to Windward Side

If you're planning a trip to Windward Side, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from March to May, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
February77.9°F (25.5°C)No Rain (Dry)Mostly SunnyAverageAverage
March77.7°F (25.4°C)No Rain (Dry)Mostly SunnyHighAverage
April78.8°F (26.0°C)No Rain (Dry)Mostly SunnyHighSlightly High
May80.2°F (26.8°C)Light RainMostly CloudyHighAverage
June81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly High
July82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
September82.9°F (28.3°C)Light RainMostly SunnyAverageSlightly Low
October82.6°F (28.1°C)Light RainMostly CloudyLowAverage
November81.3°F (27.4°C)Light RainMostly CloudyLowSlightly Low
December79.7°F (26.5°C)Light RainMostly SunnyLowSlightly High

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To find the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on your complete booking. Being the planner truly has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient area for you to plan new trips, manage your ongoing arrangements, or revisit and organize your reservations. Your saved or booked properties are categorized into Potential, Upcoming, or Current Trips for easy access. To discover Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Cove Bay Beach (1.2 mi / 2 km)
  • Well's Bay Beach (1.6 mi / 2.6 km)
  • Mt Scenery (0.7 mi / 1.1 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, the best area to consider is the charming neighborhood surrounding Fort Bay. This picturesque area not only provides stunning views of the Caribbean Sea but also offers convenient access to the island's hiking trails and lush landscapes. With around 10 to 15 vacation rental properties in this vicinity, you'll find a range of options to suit your preferences.

Staying near Fort Bay means you're just a short walk from the island's main harbor, where you can embark on boat trips to explore nearby islands or enjoy diving and snorkeling adventures. The renowned Mount Scenery, the highest point in the Netherlands, is also a highlight nearby, offering breathtaking hiking opportunities for outdoor enthusiasts.

Another appealing option is the Windward Side itself, which is the heart of Saba's vibrant culture. This area boasts a few cozy vacation rentals, allowing you to immerse yourself in local life while being close to attractions like the Saba Heritage Center, where you can learn about the island's fascinating history and culture.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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, travelers should focus on the picturesque coastal areas near the island's natural attractions. The vicinity around the Bottom offers stunning views of the Caribbean Sea, with several properties featuring outdoor terraces, private balconies, and panoramic vistas. Many of these rentals are equipped with amenities such as fully stocked kitchens and common areas ideal for relaxing after a day of exploration.

Nearby, the area around Fort Bay provides additional options for beach house rentals. Here, visitors can find charming cottages and villas that often include private gardens, outdoor dining spaces, and easy access to the beach for snorkeling and swimming. The atmosphere is tranquil, making it great for those seeking a peaceful getaway.

The Windward Side region is also known for its hiking trails that lead to stunning viewpoints, so travelers can expect some properties to offer amenities like gear storage for outdoor activities or proximity to trailheads.
What is the most popular type of vacation rental accomodation in Windward Side?
In Windward Side, cottages are quite popular, with several available throughout the area. These charming properties offer a cozy atmosphere, often featuring rustic decor, fully equipped kitchens, and inviting living spaces. Many cottages also provide outdoor patios or decks, allowing guests to enjoy the beautiful views of the surrounding landscape.

Additionally, there are several vacation houses and villas that cater to travelers seeking more spacious rooms. These rentals typically come with multiple bedrooms, private gardens, and outdoor seating areas, making them ideal for families or groups looking to relax together.
Are there any family house rentals in Windward Side?
In Windward Side, Saba, there are several family-friendly vacation rentals available, making it a great spot for groups seeking a unique getaway. This charming locale offers properties that typically feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy the fresh air.

Visitors will appreciate the proximity to natural attractions, including hiking trails and stunning views from the island's mountainous terrain. Many homes provide modern amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all ages.
Can I rent a vacation home with a pool or hot tub in Windward Side?
In Windward Side, Saba, travelers can find several vacation homes available for rent that feature pools or hot tubs. This picturesque area offers stunning views and a tranquil atmosphere, superb for a relaxing getaway. Many of the rentals come with amenities such as private pools, hot tubs, and spacious outdoor terraces, providing an ideal setting for enjoying the beautiful Caribbean weather. Additionally, travelers can expect fully equipped kitchens and comfortable living spaces, making these homes suitable for families or groups.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Windward Side?
In the Windward Side of Saba, there are several vacation rentals tailored for remote work. Many of these properties are equipped with essential amenities such as Wi-Fi, dedicated desks, computer monitors, and comfortable desk chairs, ensuring a productive environment for travelers.

The area is known for its stunning natural beauty, with breathtaking views of the Caribbean Sea and lush landscapes, making it an inspiring backdrop for remote work. Additionally, the proximity to various hiking trails and local attractions allows for enjoyable breaks from work. 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 travelers 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 WiFi, kitchens, and private pools. Many properties also feature outdoor decks or patios, superb for enjoying the tropical surroundings. Travelers can expect rentals equipped with modern conveniences such as blenders for preparing fresh smoothies.
When is the best time to visit Windward Side for a vacation rental?
April is the most popular month to visit the Windward Side of Saba, as it falls within the peak season from March to May. During this time, travelers flock to this stunning destination to enjoy its lush landscapes, pristine waters, and vibrant marine life. The climate during these months is typically warm and inviting, with temperatures ranging from the mid-70s to low 80s Fahrenheit, ideal for outdoor activities such as hiking the famous Mount Scenery or snorkeling in the crystal-clear waters.

For those who appreciate nature, this peak season is great for sightseeing and exploring the rich biodiversity of Saba's ecosystems. Whether you're trekking through the rainforest or relaxing on a serene beach, you'll find plenty of opportunities to soak in the island's beauty while enjoying the comfortable and pleasant weather.

If you're looking for a more budget-friendly option, consider visiting in October. While this month is part of the low season, it offers a unique charm with fewer crowds and a chance to experience the island more intimately. You can still enjoy the warm weather and take part in activities like diving or hiking without the hustle and bustle of peak tourist activity.

Ultimately, the best time to book a vacation rental in Windward Side depends on your preference for vibrant social experiences versus a more relaxed getaway.
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.
What are the top attractions in Windward Side?
In Windward Side, Saba, visitors can enjoy a unique blend of natural beauty and cultural attractions. The neighborhood is known for its stunning hiking trails, particularly the trek up Mount Scenery, which offers panoramic views of the surrounding islands. Vacation rentals in this area often provide easy access to the trailheads and a serene atmosphere for nature lovers.

Additionally, the charming village of Windward Side features colorful Caribbean architecture and local shops where travelers can experience Saban culture. The nearby Saba Marine Park is a major draw for divers and snorkelers, with vibrant coral reefs and diverse marine life. The island's rich history is also showcased at the Saba Museum, located in the area, where visitors can learn about the island's heritage and traditions.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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