South Boston holiday rentals

We found 1,215 holiday rentals — enter your dates for availability
Select from 15 houses, 13 flats and other holiday rentals to find the perfect place for your stay in South Boston. 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:11 Dec - 18 Dec

Room
Living area
Private kitchen
Room
Exceptional
(13 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
AU$7,580
for 7 nights, 1 home
AU$1,083 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Room
Interior
Interior
Bathroom
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,924
for 7 nights, 1 home
AU$846 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Outdoor dining
Living area
Room
Living area
Exceptional
(42 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,655
for 7 nights, 1 apartment
AU$1,094 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Master Bath Views
Cool Historic Details in this 1860's townhome apartment, stairs required!
Bedroom 2,
Dining
Exceptional
(46 reviews)

Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!

Boston

8% off
AU$6,861
for 7 nights, 1 apartment
AU$980 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Welcome!
Dining
Steps Required.
Interior
Exceptional
(37 reviews)

**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!

Boston

8% off
AU$6,887
for 7 nights, 1 apartment
AU$984 per night
includes taxes & fees
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Private kitchen
Dining
Living area
Living area
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,065
for 7 nights, 1 apartment
AU$724 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Room
Interior
Private kitchen
Interior
Exceptional
(27 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,622
for 7 nights, 1 apartment
AU$803 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Open Kitchen/Dining Area
Living area
Located on floor 2 of a classic Boston 1860's Rowhouse
Entrance/steps to apartment. Please note, steps required
Exceptional
(89 reviews)

Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!

Boston

8% off
AU$2,255
for 7 nights, 1 apartment
AU$322 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Room
Isabella Stewart Gardner Museum, Walking distance from Inn
Open Space with Doors available for privacy between Kitchen/ Bedroom
Fort Hill Inn, Boston. Main Building forthillinn.com
Exceptional
(83 reviews)

Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center

Boston

8% off
AU$2,255
for 7 nights, 1 apartment
AU$322 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Interior
Exterior detail
Open Kitchen
Dining
Exceptional
(5 reviews)

Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center

Boston

8% off
AU$3,820
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Fully Open, bright and airy living Space
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Newly Renovated interior of The Boston/Public Library
Located on a quiet Private Way, In The Fort Hill neighborhood.
Exceptional
(85 reviews)

Fresh Modern City Loft Apt! Easy Access to the city!

Boston

8% off
AU$2,186
for 7 nights, 1 apartment
AU$312 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!
Room
Living area
Interior
Private kitchen
Exceptional
(19 reviews)

"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center

Boston

8% off
AU$2,138
for 7 nights, 1 apartment
AU$305 per night
includes taxes & fees
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Queen size bed
Interior
Private roof deck
Dining
Exceptional
(38 reviews)

extended stays

Boston

7% off
AU$2,161
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
extended stays
Eat in kitchen
Kitchen with granite counter tops and stainless steel appliances
Room
Living room with plenty of natural light.
Exceptional
(189 reviews)

LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

Boston

8% off
AU$3,576
for 7 nights, 1 apartment
AU$511 per night
includes taxes & fees
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Open Dining with Galley Kitchen
Interior
Newly Refreshed Kitchen, Compact Dishwasher in cabinet under Sink
Located on the adjacent Private way. Outdoor Deck for guest use.
Wonderful
(34 reviews)

Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!

Boston

8% off
AU$3,785
for 7 nights, 1 apartment
AU$541 per night
includes taxes & fees
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!

  • 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, 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 home accommodation in South Boston?
The most in-demand types of holiday homes in South Boston are apartments. Hoping for something different? Stayz 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 home in South Boston?
A range of factors determine the price of a holiday home 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 home. Click on your South Boston travel dates to see your options on Stayz. Did someone just say "private pool"? Use the filters to select the features and amenities you need.
Are there pet-friendly holiday homes in South Boston?
Happily, yes. You'll find 42 holiday homes that welcome pets in South Boston on Stayz. Our cuddly best friends also need a break, so simply use our search function for pet-friendly holiday homes to book a perfect pad where your puppy dog can join in the fun.
What are popular home amenities in South Boston?
Nearby museums, a nearby waterfront and a firepit head the list of most popular home amenities in South Boston. Whether you're heading away by yourself, with your better half or a bunch of friends, Stayz will help you find a holiday home that fits your style with a load of extras you'll love.
Are there large group holiday homes 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 homes in South Boston that welcome kids?
With 42 family-friendly holiday homes 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 homes in South Boston?
You can pick from 20 one-bedroom homes 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 homes 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 homes 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 Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in South Boston?
You can pick from 42 holiday homes 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 home in South Boston?
The minimum age is usually 16, 18 or 21. It can change from property to property on Stayz, so look at the rules of your chosen South Boston stay before you book.
How long can I rent a holiday home in South Boston for?
How long you can book a holiday home 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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