Windward Side Vacation Rentals, Saba: house rentals & more

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 the best place to stay - Windward Side

Beautiful ocean view. Neighbouring islands can be seen in the distance

Saba's FInest Luxury Rental

Sleeps 12 · 5 bedrooms · 5 bathrooms

Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

Sleeps 6 · 2 bedrooms · 2 bathrooms

Top rated rentals - Windward Side

Saba relaxation

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Enjoy full kitchens, laundry, pools, yards and more
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More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Find out more about Windward Side

Why visit Windward Side

Scenic Beaches: Unwind at beautiful spots like Carolina Beach, ideal for relaxation and fun under the sun.
Cultural Exploration: Visit historical museums and ancient ruins to immerse yourself in local history and culture.
Outdoor Adventures: Engage in activities such as beach boardwalk strolls and wave runner rentals along the captivating Windward Coast.
Charming Neighborhoods: Explore the picturesque atmosphere of nearby East Hampton and other charming areas.
Diverse Accommodations: Choose from a range of vacation rentals, including luxury villas and cozy cottages.

Popular types of accommodation in Windward Side

Planning a getaway to Windward Side? The excitement begins with selecting your perfect home away from home. Explore a variety of accommodations, from charming villas and cozy cottages to modern apartments. Whether you're looking for Windward Villa, Windward Pointe, or Windward condo rentals, you'll find the ideal vacation rental that suits your needs. Discover the charm of Windward Side and enjoy a stay that offers comfort, convenience, and unforgettable memories.

Villas: Offering a luxurious escape, villas are the top choice for travelers seeking spacious accommodations and stunning views in Windward Side.
Apartments: Ideal for those who prefer a more home-like feel, apartments provide comfort and convenience with easy access to local attractions.
Cottages: Cozy and inviting, cottages offer a charming retreat for couples and families looking to unwind in a serene setting.
Houses: Perfect for larger groups, houses offer ample space and privacy for a memorable getaway.**

Top attractions in Windward Side

Windward Side offers a delightful blend of beach, culture, and outdoor adventures. Visitors can explore historical museums, picturesque beaches, and ancient ruins. For those seeking a scenic experience, activities like beach boardwalk strolls, wave runner rentals, and exploring the captivating Windward Coast are must-dos. Whether you're traveling solo or with family, Windward Side promises a memorable vacation filled with cultural richness and stunning natural beauty.

Well's Bay Beach: A picturesque beach located 2 miles from Windward Side, Well's Bay Beach offers a relaxing atmosphere with its soft sand and gentle waves, perfect for sunbathing and enjoying beach vibes.
Dutch Museum of Saba: Situated within Windward Side, this museum provides a deep dive into Saba's rich history and cultural heritage, showcasing local artifacts and stories that reflect the island's unique identity.
Mt Scenery: Just 0.7 miles away, Mt Scenery is the island's highest point, offering adventurous hiking trails with breathtaking views and a chance to experience the natural beauty of Saba.

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

When planning your trip, whether you’re traveling with a group, family, pets, or seeking extended stays, be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to guide you.

Traveling to Windward Side with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
Traveling to Windward Side with young kids: Traveling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, looking for accommodations close to family-friendly attractions can enhance your experience.
Taking your pets with you to Windward Side: For many families, a vacation just isn't the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Windward Side: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Windward Side

Windward Side offers a perfect blend of beach, culture, and outdoor adventures. Visitors can enjoy stunning ocean views, unwind at Carolina Beach, and explore the charming atmosphere of nearby East Hampton. Whether you're seeking a luxurious getaway or a romantic escape, the windward coast is home to ideal beach homes and scenic spots that make for an unforgettable vacation experience.

The Bottom: Located about a mile from Windward Side, The Bottom is the capital of Saba and a hub for culture and outdoor activities. Visitors flock here for a rich blend of history and nature. The area boasts beautiful hiking trails that lead to stunning viewpoints, making it perfect for outdoor enthusiasts. You can also enjoy a round of golf at the local golf course. Don’t miss the Saba Heritage Center, where you can learn about the island's history, or take a stroll to the nearby beach for some relaxation in the sun.
Hell's Gate: Just under a mile from Windward Side, Hell's Gate is a charming coastal area known for its stunning beaches and natural beauty. The serene atmosphere is perfect for travelers seeking a peaceful beach experience. Spend your day lounging on the sandy shores, swimming in crystal-clear waters, or exploring the nearby nature trails. Whether you’re looking for a quiet spot to unwind or a picturesque place to take photos, Hell's Gate offers plenty of opportunities to connect with nature.
Upper Zion's Hill: Situated in the vicinity of Windward Side, Upper Zion's Hill is renowned for its beautiful beaches, including a popular nudist beach. This area is ideal for sun-seekers and those looking to embrace a more relaxed lifestyle. The beaches here provide a tranquil escape, perfect for swimming, sunbathing, or simply enjoying the breathtaking views of the Caribbean Sea. Whether you’re looking to socialize or find a quiet spot, Upper Zion's Hill has something for everyone.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	78.4°F (25.8°C)	No Rain (Dry)	Mostly Sunny	Average	Average
February	77.9°F (25.5°C)	No Rain (Dry)	Mostly Sunny	Average	Average
March	77.7°F (25.4°C)	No Rain (Dry)	Mostly Sunny	High	Average
April	78.8°F (26.0°C)	No Rain (Dry)	Mostly Sunny	High	Moderately High
May	80.2°F (26.8°C)	Light Rain	Mostly Cloudy	High	Moderately Low
June	81.5°F (27.5°C)	Light Rain	Mostly Sunny	Average	Moderately Low
July	82.0°F (27.8°C)	Light Rain	Mostly Sunny	Average	Average
August	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Average	Moderately High
September	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Average	Average
October	82.6°F (28.1°C)	Light Rain	Mostly Cloudy	Low	Moderately Low
November	81.3°F (27.4°C)	Light Rain	Mostly Cloudy	Low	Average
December	79.7°F (26.5°C)	Light Rain	Mostly Sunny	Low	Moderately High

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and the ability to earn and redeem OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform to plan new trips, continue your previous arrangements, or manage your travel plans effectively. You can easily access your saved or booked properties, which are organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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:

Mt Scenery (0.7 mi / 1.1 km)
Well's Bay Beach (1.6 mi / 2.6 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

How much does it cost to rent a vacation rental in Windward Side?

Property type, length of stay and time of year are some of the things that can influence the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From quaint country cottages to expansive luxury villas, all Vrbo vacation rentals offer terrific value.

How much does it cost to rent a beach house in Windward Side?

The average price for a vacation rental near the beach in Windward Side depends on when you’re traveling and the type and size of property you want. Find prices easily on Vrbo by entering your destination and preferred travel dates. Then use the filters to select the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a pool.

What are the top attractions for families in Windward Side?

There are plenty of awesome things to see and do with the family in Windward Side, such as:

Dutch Museum of Saba
Saba Heritage Center
Harry L Johnson Museum

How old do you have to be to rent a vacation rental in Windward Side?

The minimum age requirements can differ between properties on Vrbo, so check the rules of the vacation rental in Windward Side you want to book. But usually, it’s 16, 18 or 21.

How long can I rent a vacation rental in Windward Side for?

It’s down to the Windward Side property. To browse a list of options offering extended stays, simply type your dates and guest number into Vrbo’s search page. Enjoy having the whole place to yourself, along with amenities such as a full kitchen, air conditioning and a backyard where the kids can run and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

Does Vrbo offer discounts for vacation homes in Windward Side?

Short stay or a well-deserved long vacation, Vrbo has some exclusive deals and discounted options in Windward Side that’ll match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the ideal place to stay — without breaking the bank.