Holiday houses in South Boston

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Top-rated holiday rentals in South Boston

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Guest favourite

Private room in South Boston

4.86 out of 5 average rating, 628 reviews

Large Private Bedroom & Bathroom by the Seaport

This is the original master bedroom in a single family home in South Boston. The private room is quite spacious with walk-in closet, Queen size bed, mini-fridge, ceiling fan, A/C & heat. There is a bathroom right outside the room that is for your private use. Please note parking is not included but there is street parking in the area. The house is close to several popular local restaurants and bars in the area. Perfect spot if you are going to the Boston Convention Center and the Seaport area.

Top Guest favourite

Apartment in South Boston

5 out of 5 average rating, 97 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Guest favourite

Apartment in South Boston

4.93 out of 5 average rating, 151 reviews

2 BDR/2b- walk to Seaport & BCEC

We welcome you to stay at our stylish apartment in South Boston (Southie)! Located next to West Broadway, South Boston’s main road with plenty of restaurants, coffee shops, groceries, and boutique stores. Located walking distance to the Seaport District, Convention Center (BCEC), and our local Southie beaches. The space is ideal for travelling professionals, small families, couples, and those looking for a true neighborhood experience, tucked away just minutes from all the big city attractions.

Guest favourite

Home in South Boston

4.89 out of 5 average rating, 36 reviews

Three level townhouse near South Boston's Best!

Welcome to our spacious, pet-friendly townhouse, steps from South Boston's best bars, restaurants, and shops! This cozy home features 2 bedrooms, 1.5 baths, a fully stocked kitchen, and a fun bar cart. Relax in the lounge area with a pull-out trundle couch or enjoy the private patio with bistro lights. Perfect for families, we offer a Pack n Play crib and a workspace. Enjoy premium amenities, plush towels, and a coffee/tea selection. Just a 20-min walk to the beach and 10 mins to the airport!

Apartment in South Boston

4.91 out of 5 average rating, 69 reviews

South Boston. Minutes away from Convention Center

In the Heart of South Boston, walking distance to restaurants, coffee shops, bars and nightlife. Less then 1 mile from the convention center. 5 min in Taxi or Uber. #7 Bus from corner will drop you right outside Convention Center. 1 mile from children's museum accessible to downtown Boston via bus from the corner of our street. Bus will also take you to the Red line subway service which can access all subway MBTA lines. 1 block from the beach at pleasure bay and parks and Castleisland.

Superhost

Condo in South Boston

4.86 out of 5 average rating, 109 reviews

Penthouse 2 Beds /2 Baths luxury in South Boston

Kick back and relax in this calm, stylish space. You won’t even feel like you are in the center of the city . Everything you need is within a walking distance , bars , coffee shops and many restaurants to choose from. Top floor unit, private balcony with 2 full bedrooms & 2 full bathrooms on opposite sides of the house makes traveling in groups much more comfortable. Brand new build 2023 , this is a hotel like stay professionally managed but with the comfort of a home away from home

Top Guest favourite

Guest suite in South Boston

4.97 out of 5 average rating, 521 reviews

History BCEC Cruise Beach Pvt Bath/Entry King Bed

* *5 STAR ★★★★★ **No Chores! No To-Do List!** *Yes a Private Bathroom *Sparkling Clean and Sanitized *Historic and Charming home *Luxury and Comfort *South Boston trendy neighborhood. *Dedicated Luxury Suite *Key-less Coded Access *King EuroTop Bed *Sitting area with sofa *Workstation (free wifi) *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking. Paid parking located at: 12 Drydock Ave, Boston, MA 02210

Guest favourite

Apartment in South Boston

4.97 out of 5 average rating, 209 reviews

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Guest favourite

Apartment in South Boston

4.88 out of 5 average rating, 155 reviews

Cozy suite in the city!

Enjoy a stylish experience at this centrally-located place in an extremely vibrant neighborhood of Boston. While staying at the AIRBNB, you will be in close proximity to the BCEC if you are in town for work. If you are in town for a pleasure, you will be very close to Downtown Boston, Fenway Park, the Seaport District, Faneuil Hall and the historic North End. You’ll be pleasantly surprised of how easy public transportation is to navigate around the city from the AIRBNB.

Guest favourite

Apartment in South Boston

4.88 out of 5 average rating, 105 reviews

City sanctuary - garden terrace - ocean view

Large sunny, private studio with stunning views and terrace overlooking the ocean, garden and JKF library, across the street from famous historic park Dorchester Heights. 2 blocks from beach. Close to convention center, airport, downtown, bus and trains. Easy walk to great local shops and haunts! Unit now equipped with Forbes #1 vetted best mattress - the Nectar Premier Hybrid Copper Queen mattress and there is a full size pull out futon

Guest favourite

Condo in South Boston

4.98 out of 5 average rating, 124 reviews

Perfectly Renovated Home w/ Private Outdoor Oasis

COMPLETELY PRIVATE - NO SHARED SPACE OTHER THEN WASHER/DRYER AREA IN BASEMENT! Enjoy a private kitchen, 2 bedrooms, 2 baths and private outdoor space. The Master Bedroom has a king Bed with an ensuite bathroom. The Second Bedroom has a queen bed, gas fireplace and is right across from the second full bath. PARKING IS NOT INCLUDED. **outdoor furniture will be put away for the Winter in November & reassembled mid-May*

Guest favourite

Apartment in South Boston

4.8 out of 5 average rating, 5 reviews

South Boston 3bdr BCEC & Seaport

Experience South Boston from our spacious, cozy apartment just a short walk from Broadway! Walk to cafes and boutiques, dine at our highly rated neighborhood restaurants, and explore nearby Seaport, BCEC (Convention Center), and our local beaches. Perfect for professionals, couples, small families, and anyone seeking a genuine neighborhood feel—just minutes from downtown Boston’s top attractions.