Apartment holiday rentals in South Boston Waterfront

Cozy 2-Bedroom in Heart of Southie

COMPLETELY PRIVATE IN-LAW SUITE! 2-bedroom/1-bathroom apartment with its own PRIVATE ENTRANCE, PRIVATE KITCHEN and PRIVATE LIVING ROOM! The only “shared” space is the washer/dryer room. We are 5 blocks from the beach, 1/2 block from Broadway (bars, restaurants, boutiques). We are a great way to see the city for much less than a hotel. Full kitchen, Charming fireplace, unique furniture, each room has central heat and AC! We do not provide parking. Local garage availability through SpotHero app.

Location · Family · Accuracy

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!

Location · Family · Hospitality

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.

Value · Location · Layout

City Sanctuary Private Terrace and Ocean Views

WORLD CUP -TALL SHIPS -4th of July - sunny private studio in one of Boston’s most scenic neighborhoods. Private terrace, across from historic Dorchester Heights Park. LOCATION—walking distance to Castle Island, entry to Boston Harbor where ships will be at full mast. 2 blocks from beach - easy access to Seaport, downtown, airport, and public transit to Stadium for World Cup. The neighborhood is a true gem with great shops, cafés, and dining.  This peaceful studio offers a perfect home base.

Location · Value · Indoor spaces

Quiet brownstone close to city

Welcome! Our cozy 2 bedroom (king+queen beds) haven offers the best: quiet yet close to everything. Piers Park's stunning water & city views are a 2-min walk. 4-min Uber to the airport, 3-min walk to subway (2 stops from downtown), and ferry to Aquarium/North/Seaport. Nearby, find affordable groceries, 4.5+ star dining, and a yoga studio next door. Recently renovated in New England brownstone style. Parking available 3 mins away for an additional fee. Join us for an amazing stay!

Family · Location · Parking

Charming South End Duplex (Pets Ok)

Ground floor duplex with backyard. In the heart of the South End. The best restaurants and coffee shops in Boston are within 1-2 blocks. We are pet friendly with a dog park 1 block away. A Victorian brownstone with 2 floors and a big backyard. 2 separate bedrooms (queen beds) with exposed brick and heavy duty AC units in each BR. The third bed is a queen sized Serta air mattress(easily inflatable) A massive parlor level, very spacious. Easily the best neighborhood in Boston.

Family · Value · Sleep quality

Southie Condo-By Subway-Bring Pets-Pool Table

Spacious 2-bedroom condo in vibrant South Boston’s Andrew Square! Just a 5-minute walk to the Red Line and under 10 minutes to top bars, restaurants, and breweries. Sleeps up to 6 with two cozy bedrooms and a large living room which features a versatile pool table that converts into a ping pong or dining table. Enjoy a full kitchen, fast WiFi, smart TV, and easy access to downtown, the Seaport, and beaches. Perfect for groups, families, or business travelers visiting Boston!

Family · Location · Barbecue

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

Value · Location · Comfort

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.

Value · Family · Condition

Nxt to ocean, 5 min dntwn by T

Embark on an urban escape! Immerse yourself in our chic 2BR/1B + office retreat, ideal for up to 4 guests. Enjoy fast WiFi, steps away from an oceanfront park with stunning Boston skyline views. Walk to the Blue Line T station, one stop to downtown or the airport. Safe, historic neighborhood with restaurants, bars, yoga, sailing, and galleries. Not suitable for children, NO PARKING/pets/smoking/cannabis/parties. Make this urban oasis your next unforgettable getaway!

Location · Family · Decor

Beacon Hills Studio next to State house 3

Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.Take it easy at this unique and tranquil getaway.

Family · Value · Shared spaces

Pet-friendly stay w/ backyard near Red Line

Welcome to this private South Boston apartment on Telegraph Hill! - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio, outdoor dining area & fully fenced backyard w/ sun loungers - Private entrance & keypad self check-in - Full kitchen w/ GE gas stove, dishwasher & coffee maker - 55" HDTV w/ Roku, dedicated workspace & high-speed WiFi - In-unit washer & dryer, pet-friendly & long-term stays welcome

Family · Value · Comfort