Holiday rentals with outdoor seating in South Boston

Family Friendly City Oasis! 2 Free Parking Spots!

Welcome to The Southie House! An epic private home for a family vacation or conference in the Heart of Boston! Close to the Red line T for access to downtown, Cambridge & local universities, and short ride to the BCEC. At the same time a short walk to the beach for relaxing. Enjoy the back yard oasis with the whole group! This home provides you with a private place to relax after a full day of exploring, ensuring you have all the comforts of home while traveling. COME SEE OUR NEW GAME-ROOM & GYM

Beautiful, spacious South Boston Condo, Near T

This beautiful townhouse is a 3 min walk to the Andrew Square (subway) station that can take you to anywhere you want in Boston or the surrounding area. Museums, colleges, Fenway Park, TD Garden, the Common, Harvard Square, Faneuil Hall, Cape Cod, Salem, the Convention Center, Boston Harbor and cruise ship terminals are many of the places you can visit. We are also a 15 min walk to the local beaches. Although the place can sleep 6, we only allow 4 guests unless arrangements are made with host.

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.

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.

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

Ideal for families with young children, traveling professionals, campus visitors, and tourists! Spacious and recently renovated townhome in South Boston: 3 miles from Logan Airport, 3miles Fenway Park, 2 miles to Seaport, 1 mile to the Boston Convention Center, 1.6 miles to South Station (Commuter Rail/Amtrak), <1 mile to the Red Line (Broadway T-Station) to Kendall Sq (Harvard, MIT) and 1 block from the 9 Bus to Copley (~15min ride to Copley Sq). Great location for World Cup visitors!

Elegant retreat w/ patio & full kitchen

Welcome to your private South Boston retreat on Telegraph Hill - a quiet, comfortable apartment steps from the Red Line and the best of the Seaport. - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio & fully fenced backyard w/ outdoor furniture - Full kitchen w/ GE gas stove, dishwasher & coffee provided - 55" HDTV w/ Roku, dedicated workspace & high-speed Wi-Fi - In-unit washer & dryer, central A/C & private entrance - Pet-friendly | self check-in | long-term stays welcome

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!

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

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.

Boston Rooftop Retreat

A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

Beautiful condo with city benefits

Nicely decorated two bedroom, one bath, spacious kitchen, dinning room, living room, back yard and deck, steps from JFK T-Stop, and short 10 minute commute to all that downtown Boston has to offer. Located blocks away from I-93 for easy access. Dorchester Brewing Company, 224, Dbar, Sugar Bowl, and Savin Bar and Kitchen are all within walking distance. My condo is located within a 5 minute walk to Carson Beach.