South Side holiday lettings

We found 23 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in South Side to find one that's perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, including parking and a garden. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in South Side?
In South Side, apartments are a popular choice for holiday rentals, with several available throughout the neighbourhood. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and often access to shared outdoor spaces. They provide a convenient option for travellers looking to experience the local culture while enjoying home-like comforts.
How much does it cost to rent a holiday home in South Side?
Prices for holiday rentals in South 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 South 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 South Side holiday house rentals?
You can find great discounts on house rentals in South 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.
Are there any South Side holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South 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.
Can I find long-stay holiday rentals in South Side?
A long-stay holiday rental in South 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.
When is the best time to visit South Side for a holiday rental?
April is the most popular time to visit South Side, Massachusetts, as spring brings a vibrant energy to the area. This season, spanning from March to May, attracts a diverse range of travellers, eager to explore the local culture, enjoy outdoor activities, and partake in various community events. During this time, the weather typically ranges from around 10 to 15 degrees Celsius, creating a pleasant atmosphere for sightseeing and leisurely strolls.

March marks the beginning of the peak season, with visitors enjoying the blossoming parks and the revitalised cityscape. As the temperatures gradually rise, outdoor enthusiasts can take advantage of the many parks and green spaces, great for picnics or casual walks. The community often hosts festivals and events that highlight local arts and music, making it an enriching experience for all.

For those seeking a more budget-friendly option, December offers a unique charm with festive decorations and a quieter pace. While it's generally considered the low season, the holiday spirit brings a cosy atmosphere, allowing you to explore the area's seasonal attractions without the usual crowds.
Are there any remote work holiday rentals in South Side?
In South Side, Massachusetts, there are several holiday rentals suitable for remote work. Many of these properties come equipped with dedicated workspaces, including desks and desk chairs, alongside reliable Wi-Fi to facilitate productivity. The area offers a mix of modern apartments and charming homes, providing comfortable settings for travellers balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Side holiday rental?
Book your South Side holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in South Side?
In South Side, Massachusetts, visitors can explore a range of attractions that highlight the area's rich cultural and historical significance. The iconic South End is known for its Victorian brownstones and vibrant art scene, featuring numerous galleries and the renowned Boston Centre for the Arts. Holiday rentals in this neighbourhood often provide easy access to popular dining spots and local boutiques.
Can I change or cancel my South Side home rental booking on Vrbo?
To find South Side holiday 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 cabin or a beach house, 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 South Side holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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