South Boston vacation rentals

We found 1,042 vacation rentals — enter your dates for availability

Discover a selection of 117 apartments, 15 condos, and other vacation rentals in South Boston that are perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, such as parking and a hot tub. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.
  • 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 South Boston

Find out more about South Boston

Why visit South Boston

  1. Cultural richness: South Boston offers a blend of urban charm and historical allure, providing a vibrant cultural experience.
  2. Outdoor activities: Enjoy a variety of parks and recreational spaces perfect for family outings and relaxation.
  3. Historic colleges: Explore renowned educational institutions that contribute to the area's rich heritage.
  4. Diverse accommodation: Choose from stylish apartments, modern condos, and private homes to suit your vacation needs.
  5. Friendly neighbourhoods: Experience the welcoming atmosphere of South Boston and nearby areas like the South End and downtown.

Popular types of accommodation around South Boston

Planning a getaway to South Boston? The excitement of choosing your accommodation awaits! Discover a range of popular vacation rentals, including private homes, stylish apartments, and modern condos. Whether you're looking for condos in Boston with swimming pools or spacious apartments for rent, South Boston has something for everyone. Dive into your options and find the perfect spot for your next adventure!

  • Houses: The top choice for visitors seeking a home-like atmosphere in South Boston, ideal for families and groups looking for space and comfort.
  • Apartments: A popular option for those who prefer a blend of convenience and privacy, perfect for solo travellers or couples.
  • Condos: A fantastic alternative offering modern amenities and often a community feel, suitable for short or extended stays.
  • Cottages: Quaint and charming, these are perfect for a cozy getaway with a touch of rustic charm.
  • House Boats: An adventurous choice for those wanting a unique experience on the water, combining comfort with aquatic living.**

Top attractions around South Boston

South Boston is an excellent destination for business, family, and city-themed vacations. Visitors can explore popular attractions such as urban parks, historic colleges, and event venues, which provide a rich cultural experience. Whether you're seeking outdoor activities or immersing yourself in the city's vibrant atmosphere, South Boston offers a variety of points of interest that cater to diverse travellers looking for adventure and relaxation.

  1. Fenway Park: A historic sports stadium, Fenway Park is a must-visit for sports enthusiasts, showcasing the vibrant culture of Boston. Experience the thrill of a Red Sox game in one of the oldest ballparks in the country, just 4.8km away from South Boston.
  2. TD Garden: Located 3.2km from South Boston, TD Garden serves as a premier event venue, hosting everything from concerts to sports events, making it a hub of business and entertainment vibes.
  3. Boston Common: This urban park, situated 3.2km from South Boston, offers a peaceful retreat with family-friendly activities and beautiful outdoor spaces, perfect for leisurely strolls in the heart of the city.

Things to do recommended for couples

For a romantic getaway in South Boston, enjoy live music at House of Blues, embark on an adventurous sailing experience with Courageous Sailing Center, or immerse yourselves in culture at the Roxbury Center for Arts. Each spot offers a unique vibe perfect for couples!

Things to do recommended for families

Your family will love the vibrant sports atmosphere at Agganis Arena, explore the wonders of the universe at Charles Hayden Planetarium, and unwind in nature at Chestnut Hill Reservation, each offering a unique experience just a short drive from South Boston.

Things to do recommended for groups

In South Boston, your group can explore the bustling Faneuil Hall Marketplace for shopping and dining, catch a captivating show at the Charles Playhouse, or enjoy a fun tour and tasting at Harpoon Brewery, perfect for making lasting memories together.

What do I need to keep in mind when booking a vacation around South Boston

When planning your trip—whether you're travelling with a group, family, pets, or seeking extended stays—it's important to prioritize your preferences effectively. Here are some helpful Vrbo booking tips for you.

  • Traveling to South Boston with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to South Boston with young kids: Travelling with young children can present its 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 South Boston: For many families, a vacation isn’t truly complete without their furry companions. If that resonates with you, explore the Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting South Boston: If you’re in search of vacation rentals offering great deals 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 adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay around South Boston

South Boston offers a vibrant mix of urban charm and historical allure, perfect for family getaways, romantic escapes, or business trips. Explore the lively streets of South Boston and its nearby neighbourhoods, like the South End and downtown Boston, where friendly locals and scenic views await. With a rich atmosphere that blends culture and community, visitors will find plenty to enjoy—from family-friendly activities to business opportunities, making it an ideal destination for all types of travellers.

  • Downtown Boston: Located a mere 3.2km from South Boston, Downtown Boston is the vibrant heart of the city, offering a rich blend of history, culture, and modern convenience. Visitors are drawn to its iconic landmarks, including historic sports stadiums and event conference venues. The area boasts a variety of family-friendly activities, shopping centres, and educational attractions. Strolling through the streets, you’ll encounter historic buildings alongside contemporary architecture, making it perfect for those interested in experiencing the dynamic pulse of urban life.
  • Seaport District: Just 1.6km from South Boston, the Seaport District has rapidly transformed into a buzzing hub for business and leisure. This waterfront area is renowned for its modern shopping centres, lively casinos, and beautiful views of Boston Harbour. The Seaport is an excellent destination for families and professionals alike, with numerous event venues and convention centres that host a variety of gatherings. As you explore, enjoy the scenic waterfront, pop into trendy eateries, and take in the neighbourhood's vibrant atmosphere.
  • Back Bay: Approximately 3.2km from South Boston, Back Bay is celebrated for its stunning Victorian brownstones and upscale shopping experiences. A favourite among families and culture enthusiasts, this neighbourhood features renowned urban parks, historic sports stadiums, and educational establishments. Visitors can leisurely stroll along the picturesque streets, enjoy shopping at high-end boutiques, or relax in the lush green spaces. Back Bay beautifully combines the charm of old-world architecture with a contemporary urban vibe, making it a must-visit locale.

Best time to go to South Boston

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyModerately HighSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyModerately HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnyModerately LowAverage
November44.4°F (6.9°C)Light RainMostly SunnyModerately LowAverage
December36.3°F (2.4°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next getaway? It might be helpful to remain flexible with your travel dates, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options!

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can easily initiate new trips, continue your previous planning, or manage your itineraries. You'll discover your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in South Boston?
The most in-demand types of vacation rentals in South Boston are apartments. Hoping for something different? Vrbo offers a variety of options to match the unique needs of our guests, so you’ll see vacation homes in loads of sizes and shapes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a vacation rental in South Boston?
A range of factors determine the price of a vacation rental in South Boston, including the season, length of stay and type of property. But, all of our vacation homes have something in common — unbeatable value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in South Boston?
When you travel and the style and size of the property will influence the cost of your beachside vacation rental. Click on your South Boston travel dates to see your options on Vrbo. Did someone just say “private pool”? Use the filters to select the features and amenities you need.
Are there pet-friendly vacation rentals in South Boston?
Happily, yes. You’ll find 42 vacation homes that welcome pets in South Boston on Vrbo. Our cuddly best friends also need a break, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your puppy dog can join in the fun.
What are popular rental amenities in South Boston?
Nearby museums, a nearby waterfront and a firepit head the list of most popular rental amenities in South Boston. Whether you’re heading away by yourself, with your better half or a bunch of friends, Vrbo will help you find a vacation home that fits your style with a load of extras you’ll love.
Are there large group vacation rentals in South Boston?
With six South Boston vacation homes that can accommodate five or more people, you can invite a few extra friends or family members along. Whether you’re planning an informal get-together or a celebratory event, we’ll help you find the perfect space to fit the occasion.
Are there vacation rentals in South Boston that welcome kids?
With 42 family-friendly vacation rentals to pick from in South Boston, now is a superb time to introduce your children to the pleasures of travel. Check our “Properties good for families” filter box to find stays that come with amenities ideal for traveling families, like full kitchens, outdoor spaces, bunk beds and entertainment units.
What are the top attractions for families in South Boston?
You’ll find loads of wonderful things to see and do with the family in South Boston, including:

  • New England Aquarium
  • Museum of Science
  • Boston Tea Party Ship

Are there one-bedroom vacation rentals in South Boston?
You can pick from 20 one-bedroom rentals in South Boston. Whether you’d like a cozy cottage or a fancy condo, our one-bedroom properties are ideal if you don’t require a lot of space. One of the main perks of having your own pad? You won’t need to share your getaway with strangers.
Can I find two-bedroom vacation rentals in South Boston?
You can select from 13 two-bedroom vacation properties in South Boston. Give the kids the second room or fill it with a couple of your favorite people. There’s enough space for whoever’s fortunate enough to be coming along.
Are there vacation rentals with WiFi in South Boston?
Whether you want to stay in touch with the news, write a few emails or update your social media, there are 10 vacation homes with WiFi in South Boston. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in South Boston?
You can pick from 42 vacation rentals with air conditioning in South Boston giving you that cool, cool breeze and extra comfort level. Enter your chosen travel dates and then make use of our filter tool to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in South Boston?
The minimum age is usually 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your chosen South Boston stay before you book.
How long can I rent a vacation rental in South Boston for?
How long you can book a vacation rental in South Boston varies according to the property. Just enter your selected travel dates to look at a list of options offering extended stays. With a range of features such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to find a terrific place to call your home away from home in South Boston.

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