Apartment holiday rentals in South Boston

Walk! Walk! Kenmore Square - 2 Beds / 1 Bathroom

2 beds / 1 bathroom apartment in the middle of everything! Located right in Kenmore Square, steps from subway station and Famous Citgo Sign. Walking distance to Fenway Park, Back Bay, restaurants, bars, and more! Walk walk walk everywhere! Next to Boston University and in front of Charles River Esplanade. Very close to Downtown, Cambridge, Longwood Medical Area, supermarkets, and way so many cool places! Includes everything you'll need for your stay. Super safe and convenient neighborhood! :)

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!

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

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.

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

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.

Bright Brownstone Condo - Terrace+ParkView

Welcome to this beautifully renovated 3-bedroom, 2.5-bath condo located in a classic 1899 brownstone in the historic Roxbury neighborhood. With park views, soaring 10-foot ceilings, and modern finishes throughout, this home blends Boston charm with contemporary comfort. The open and airy layout features a sleek, fully equipped kitchen, a spacious living room ideal for relaxing or entertaining, and a private terrace where you can unwind and enjoy stunning sunset views.

The Washington - The Upton Boston, South End

Owner operated, and lovingly care for, the Upton is located in the heart of the South End, The Washington is the ideal home base. You are minutes from restaurants, shopping, cafes, site seeing, art galleries, or visiting with your family in the South End. We love the apartment's original Victorian architecture & fixtures: high ceilings, expansive windows, quaint street views, 300 MBPS WiFi, streaming services & a Casper bed. We look forward to hosting your stay!

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

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.