99+ Private Villas and Holiday Rentals in South Boston |
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South Boston Holiday Rentals

About Casai's Private Villas and Holiday Rentals in South Boston

Discover more than 99 vacation rentals available in South Boston. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in South Boston.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in South Boston, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near South Boston. On average, places to stay near South Boston offer 598.36 ft², with nightly prices averaging CA $645.

With Casai, finding and comparing holiday rentals in South Boston is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in South Boston

Type Count
Holiday Apartments 66
Vacation Homes 22

Use these Quick Filters to Find a Holiday Rental in South Boston

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in South Boston.

Weather in South Boston, MA

View the weather forecast for South Boston before booking your South Boston Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay in South Boston, MA


Columbus Park - Andrew Square 2,926 Properties
Our Lady of Czestochowa Roman Catholic Church 2,859 Properties
Columbus Park 2,811 Properties
Bunker Hill Monument 2,606 Properties
John F Kennedy Presidential Museum Library 2,508 Properties
L Street Beach 2,291 Properties
M Street Beach 2,230 Properties
City Point 2,118 Properties
Marine Park 2,090 Properties
Tory Row 2,068 Properties
Edward Kennedy Institute for the US Senate 2,068 Properties
Telegraph Hill 1,418 Properties

Frequently Asked Questions About South Boston?

What are the top holiday rentals in South Boston?

With numerous options available in South Boston, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in South Boston:

Which holiday homes in South Boston are best for families?

If you're searching for a family-friendly holiday home in South Boston, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in South Boston:

How many Casai.ca holiday rentals are available in South Boston?

As of 2025, Casai boasts over 99 properties listed in the South Boston area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in South Boston.

Nearby Neighborhood (8) 
Neighborhood Property Count
Seaport District Vacation Rentals in Boston, Massachusetts 139
D Street - West Broadway Vacation Rentals in Boston, Massachusetts 139
Telegraph Hill Vacation Rentals in Boston, Massachusetts 1418
Columbus Park - Andrew Square Vacation Rentals in Boston, Massachusetts 2926
Harrison Lenox Vacation Rentals in Boston, Massachusetts 645
South of Washington Vacation Rentals in Boston, Massachusetts 643
Fort Point Vacation Rentals in Boston, Massachusetts 2915
City Point Vacation Rentals in Boston, Massachusetts 2118

People Also Ask

There are 99 South Boston, MA Holiday Rentals

Recently Booked Holiday Rentals in South Boston