Windward Side holiday rentals

We found 10 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.

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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:

  • Mt Scenery (0.7 mi / 1.1 km)
  • Cove Bay Beach (1.2 mi / 2 km)
  • Well's Bay Beach (1.6 mi / 2.6 km)
  • Sulfur Mine (1.2 mi / 1.9 km)
  • Great Hill (1.6 mi / 2.6 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 best area to stay in Windward Side when booking a holiday rental?
When considering a holiday rental in Windward Side, Saba, you'll find that this charming area offers a unique blend of natural beauty and local culture. The Windward Side is renowned for its stunning landscapes, characterised by lush mountains and breathtaking views of the Caribbean Sea. The area is home to a limited number of properties, providing a more intimate and tranquil experience for visitors.One of the top attractions nearby is the Saba National Marine Park, which is a haven for snorkelling and diving enthusiasts, showcasing vibrant coral reefs and an abundance of marine life. Additionally, the picturesque village of Windward Side itself boasts lovely local shops and eateries, where you can experience the island's hospitality and culinary delights.The scenic hiking trails, particularly those leading to Mount Scenery, offer adventurous guests the opportunity to immerse themselves in the island's natural beauty while enjoying panoramic views from the summit.
Where are the best areas for renting a beach house in Windward Side?
For renting a beach house in Windward Side, Saba, travellers should consider the scenic locations along the coastline that offer stunning views of the Caribbean Sea. The area near the island's capital is ideal, as it provides access to beautiful beaches and opportunities for snorkelling and diving. Many of the beach houses here come equipped with amenities such as outdoor terraces, private gardens, and fully furnished kitchens, making them great for families or groups seeking a relaxing seaside getaway.Additionally, properties located close to the hiking trails leading to Mount Scenery, the island's highest point, offer a unique combination of beach access and mountainous adventure. These rentals often feature amenities like spacious living areas, balconies with panoramic views, and sometimes even provisions for outdoor activities, including gear for snorkelling or hiking.Windward Side also has charming local shops and restaurants within walking distance, allowing travellers to immerse themselves in the island's culture and cuisine.
What is the most popular type of holiday rental accomodation in Windward Side?
In Windward Side, cottages and villas are the most popular types of holiday rentals, with several options available throughout the area. These accommodations typically provide a charming and homely atmosphere, making them ideal for visitors looking to immerse themselves in the natural beauty of Saba. Most cottages and villas come equipped with essentials such as fully furnished kitchens, spacious living areas, and outdoor terraces or patios where guests can enjoy the stunning views of the surrounding landscape.
Are there any family house rentals in Windward Side?
In Windward Side, Saba, there are several family-friendly house rentals available, suiting groups seeking a memorable experience. The area is known for its stunning natural beauty and welcoming atmosphere. Many of these properties feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for relaxation or play.Visitors can enjoy amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. The proximity to nearby attractions like the scenic hiking trails of Mount Scenery and the beautiful beaches provides ample opportunities for outdoor adventures. Additionally, the local community offers a taste of island life, with markets and cultural experiences nearby.
Can I rent a holiday home with a pool or hot tub in Windward Side?
In Windward Side, Saba, there are several holiday homes available for rent that feature pools, providing a wonderful option for travellers looking to relax in the tropical climate. This charming area is known for its stunning views and lush landscapes, making it an ideal location for a getaway. Many of the properties come equipped with private pools, outdoor seating areas, and fully equipped kitchens, great for enjoying leisurely meals with family or friends.Additionally, some rentals may offer hot tubs, allowing guests to unwind after a day of exploring the island's natural beauty.
Are there any remote work holiday rentals in Windward Side?
In Windward Side, Saba, there are around 10 remote work holiday rentals available, making it an excellent choice for those looking to blend work and leisure. This picturesque area offers a tranquil environment with stunning views of the surrounding landscape, ideal for productivity. Many of the properties are equipped with essential amenities for remote work, including reliable Wi-Fi and comfortable workspaces, ensuring a seamless working experience.Visitors can expect charming accommodations that often feature spacious living areas, fully equipped kitchens, and outdoor terraces where one can unwind after a day of work. The inviting atmosphere of Windward Side, combined with its natural beauty and proximity to local attractions, makes it a great location for remote workers seeking both comfort and inspiration. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windward Side?
In Windward Side, popular rental amenities include spacious decks or patios, kitchens, and balconies that allow guests to enjoy the stunning views of the surrounding landscape. Many properties also feature porches or lanais, providing additional outdoor space for relaxation. Additionally, travellers can expect kitchens equipped with a blender, making it easy to prepare meals and enjoy refreshing drinks during their stay.
When is the best time to visit Windward Side for a holiday rental?
The best time to visit the Windward Side of Saba for a holiday rental is during the peak season from March to May, with April being the most popular month. This period is favoured by travellers seeking to experience the island's lush landscapes and rich biodiversity, making it ideal for hiking and exploring the scenic trails that wind through the verdant hills.During these months, the climate is pleasantly warm, with temperatures typically ranging from 24 to 30 degrees Celsius. This creates a great atmosphere for outdoor activities such as snorkelling in the crystal-clear waters or simply relaxing on the beach. The vibrant flora and fauna are at their best, enhancing the overall experience and providing numerous opportunities for photography and wildlife observation.If you're looking for a more budget-friendly option, consider planning your visit in October. While this month is part of the low season, it offers a unique charm with fewer tourists, allowing for a more intimate experience of the island's tranquillity and natural beauty. You can still enjoy the warm climate while exploring the local culture at a leisurely pace.Ultimately, the best time to book a holiday rental on the Windward Side depends on whether you prefer the lively option of peak season or the serene allure of quieter months.
What are the top attractions in Windward Side?
In Windward Side, Saba, visitors can enjoy the stunning views from Mount Scenery, the highest point in the kingdom of the Netherlands, which offers hiking trails and a chance to experience the island's lush biodiversity. The charming village itself features picturesque streets lined with traditional Caribbean architecture, and the local shops and eateries provide a taste of island life.Nearby, the Saba Marine Park is a highlight for snorkelling and diving enthusiasts, showcasing vibrant coral reefs and diverse marine life. Additionally, the Saba Dutch Heritage Museum offers insights into the island's history and culture, making it a must-visit for those interested in local heritage.For those venturing to Bonaire and Sint Eustatius, both islands are renowned for their beautiful beaches and excellent diving spots. Bonaire's Washington Slagbaai National Park is superb for hiking and birdwatching, while Statia's Quill National Park features lush landscapes and the opportunity to explore volcanic terrain.
Are all fees included in the Windward Side holiday homes prices shown on Stayz?
Stayz 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.
Are there any Windward Side holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Windward Side holiday homes?
You can find great discounts on holiday homes in Windward Side on Stayz, 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.
Can I change or cancel my Windward Side holiday home booking on Stayz?
To find Windward Side holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windward Side?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Windward Side holiday home?
Book your Windward Side holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windward Side?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Windward Side to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.