Coffee Hawaii - Vacation Rentals in South Boston

Charles Bass House Bed & Breakfast From US $176
         

9.8 (9 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Charles Bass House Bed & Breakfast From US $189
         

9.8 (107 Reviews)
Bed & Breakfast
  • Parking
  • Security/Safety
  • Business Services
Oak Grove B&B second-floor suite with two rooms no pets From US $178
         

10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Oak Grove B&B Queen rm. separate entrance-Pet Friendly From US $145
         

10.0 (3 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Oak Grove B&B Treehouse Queen Bed 2 Porches-Pet Friendly From US $134
         

10.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in South Boston

Over 25+ Luxury Places to Stay in or Near South Boston
Americas Best Value Inn Suites South Boston From US $499
         

4.4 (93 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Wilde Manor From US $467
         

New
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Oak Grove Bed and Breakfast From US $250
         

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9.4 (46 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • Balcony/Terrace
2 Mi to South Boston Speedway Cozy Tiny Home! From US $242
         

Studio 2 Mi to South Boston Speedway From US $241
         

New
Apartment
  • Parking
  • Accessibility
  • Security/Safety
Studio 2 Mi to South Boston Speedway From US $199
         

Top-Rated Vacation Rentals with a Pool in South Boston

Over 4+ Top-Rated Vacation Rentals with a Pool in or Near South Boston
Fairfield Inn & Suites South Boston From US $155
         

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8.8 (392 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn and Suites by Marriott South Boston From US $184
         

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7.9 (61 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn South Boston - Danville East From US $95
         

7.2 (393 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn South Boston - Danville East From US $106
         

6.6 (160 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in South Boston

Over 3+ Pet-Friendly Vacation Rentals in or Near South Boston
Super 8 by Wyndham South Boston VA From US $89
         

6.8 (166 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Americas Best Value Inn & Suites South Boston From US $72
         

5.8 (339 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Clarion Pointe South Boston - Danville East From US $110
         

6.5 (208 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in South Boston

Over 1+ Large Vacation Homes & Villas in or Near South Boston
Oak Grove Bed and Breakfast From US $120
         

9.2 (17 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Wheelchair Accessible Vacation Homes in South Boston

Over 1+ Wheelchair Accessible Vacation Homes in or Near South Boston
Clarion Pointe South Boston - Danville East From US $99
         

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7.2 (308 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

South Boston Vacation Rentals and Airbnb Places to Stay Under $200

Over 5+ South Boston Vacation Rentals and Airbnb Places to Stay Under $200
Masons Chapel at Springfield 1842 From US $144
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Super 8 by Wyndham South Boston VA From US $91
         

6.8 (472 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
A roomy, comfortable home close to everything. From US $99
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Home sweet home From US $157
         

New
House
  • Air Conditioner
  • Parking
  • TV
Serene lake cabin From US $145
         

New
Cabin
  • Air Conditioner
  • Designated Smoking Area
  • Bedding/Linens

Instantly Bookable Vacation Homes in South Boston

Over 2+ Instantly Bookable Vacation Homes in or Near South Boston

About South Boston Vacation Rentals

With more than 34 South Boston vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Coffeeshawaii and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Boston.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Coffeeshawaii South Boston, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Boston. Places to stay near South Boston are 254.8 ft² on average, with prices averaging $203 a night.

Coffeeshawaii makes it easy and safe to find and compare vacation rentals in South Boston with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Boston

Type Count
Hotels with Suites 11
Vacation Homes 10
B&B 8
Holiday Apartments 2
Cabin Rentals 1
Cottages 1
Others 1

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

Pro Tip: Coffeeshawaii makes it easy to compare the best listings on Coffeeshawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Coffeeshawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Boston.

Weather in South Boston

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

South Boston Vacation Rental Frequently Asked Questions

What are the top vacation rentals in South Boston?
How many vacation rentals are available in South Boston?

Currently, the total number of properties listed in 2026 is over 34 in the South Boston area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Boston.