South Boston holiday lettings

We found 1,049 holiday rentals — enter your dates for availability

Discover a selection of 117 apartments, 15 flats and other holiday rentals in South Boston that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as air conditioning and Wi-Fi. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - South Boston

Showing deals for:1 Aug - 8 Aug

Image gallery for Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum

Stooped brownstone entrance
9.4 out of 10 rating
Exceptional
(29 reviews)

Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum

Boston, MA

8% off
Price is £2,389
£341 per night
includes taxes & fees
Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum

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 accommodation in South Boston?
The most in-demand types of holiday 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 holiday 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 holiday rental in South Boston?
A range of factors determine the price of a holiday rental in South Boston, including the season, length of stay and type of property. But, all of our holiday 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 holiday 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 holiday rentals in South Boston?
Happily, yes. You’ll find 42 holiday 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 holiday 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 holiday home that fits your style with a load of extras you’ll love.
Are there large group holiday rentals in South Boston?
With six South Boston holiday 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 holiday rentals in South Boston that welcome kids?
With 42 family-friendly holiday 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 travelling 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 holiday rentals in South Boston?
You can pick from 20 one-bedroom rentals in South Boston. Whether you’d like a cosy 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 holiday rentals in South Boston?
You can select from 13 two-bedroom holiday properties in South Boston. Give the kids the second room or fill it with a couple of your favourite people. There’s enough space for whoever’s fortunate enough to be coming along.
Are there holiday 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 holiday homes with WiFi in South Boston. Check the “WiFi” box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in South Boston?
You can pick from 42 holiday 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 holiday 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 holiday rental in South Boston for?
How long you can book a holiday 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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