Holiday houses in South Boston Waterfront

4.86 out of 5 average rating, 58 reviews

A cozy living area is highlighted by a navy blue sofa adorned with decorative throw pillows. A small marble coffee table is topped with a candle and design-related books. Fresh greenery is placed in a neutral vase, adding a touch of nature to the space.

Home in South Boston

Single House 2BR - Backyard+Walk to BCEC & Seaport

Perfectly located for exploring Boston, our home places you minutes from Downtown, Seaport, and Logan Airport. Whether you’re here for a conference at BCEC, waterfront dining, or exploring the city, you’ll have access to everything Boston has to offer. Enjoy a convenient stay near the Seaport, with the BCEC within walking distance, from this bright and modern single-family home with a private backyard, rare find in the city! **Street & off-site parking available. See description for options.

A bright bedroom features a spacious bed with light bedding and decorative pillows. Two large windows allow natural light to illuminate the room. A cozy armchair and a nightstand with lamps enhance the comfort, while a subtle area rug adds warmth to the hardwood floor.

4.93 out of 5 average rating, 213 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.

4.99 out of 5 average rating, 140 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!

Superhost

A cozy lounge area features a large flat-screen TV displaying a streaming service. Soft seating is provided with gray sofas and blue armchairs. A light-colored coffee table is centered on a blue and cream patterned rug, complementing the room's neutral walls and bright window treatments.

Home in South Boston

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!

4.9 out of 5 average rating, 68 reviews

4.89 out of 5 average rating, 150 reviews

A well-lit bedroom features a spacious bed dressed in crisp white linens, flanked by small bedside tables with lamps. Large windows provide natural light and views of the surrounding area, while the soft blue walls create a calming ambiance.

Condo in South Boston

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

4.96 out of 5 average rating, 136 reviews

A spacious living area is shown, featuring a light-colored sectional sofa, an accent chair, and a wooden coffee table. Natural light filters through large sliding doors, which open to a private deck. A soft area rug lies beneath the furniture, enhancing the cozy atmosphere.

Condo in South Boston

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!

4.96 out of 5 average rating, 27 reviews

Luxe Duplex nr Beach Seaport/Convention Cntr BCEC

NOTE: There is NO on-site parking. Please read the parking instructions below before booking. A Stylish, newly built two-level home, all to yourself! Featuring three bedrooms, a full bathroom with a spacious walk-in shower, and thoughtful amenities throughout. Just steps from vibrant shops and restaurants, 1.5 miles from the Convention Center, and offering beach views, this home is ideal for large groups or business travelers seeking a relaxed, suburban feel right in the city.

A light-filled interior features a wooden dining table positioned near a decorative fireplace. The walls are painted in soft blue, creating a calm setting. A glimpse of a modern kitchen is visible in the background, and a framed artwork adds a touch of character.

4.96 out of 5 average rating, 274 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

Superhost

A well-lit bedroom features a spacious bed with white bedding and decorative pillows. A bedside lamp stands next to the bed, and a window is dressed with long gray curtains. A mirror reflects the room's light, enhancing the sense of openness.

4.86 out of 5 average rating, 213 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.

4.94 out of 5 average rating, 260 reviews

The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.

Condo in East Boston

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

4.98 out of 5 average rating, 206 reviews

A pair of large, double doors with a rich, textured surface stands prominently in the background. The doors are flanked by warm, wooden floors and a light-colored sofa adorned with decorative pillows. A vibrant area rug adds color to the setting.

Condo in Downtown

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area- king bed, [ that can also be 2 twin xl upon request] also sofa in living room is pull-out double size bed. The bathroom is with shower and tub, a complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

4.93 out of 5 average rating, 61 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.

Popular amenities for South Boston Waterfront holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Boston Waterfront

4.95 out of 5 average rating, 82 reviews

Condo in South Boston

Bright 4BR Home | 2 Kitchens | Walk to Seaport

Apartment in South Boston Waterfront

Luxury Studio Next to Broadway icze

4.88 out of 5 average rating, 33 reviews

4.82 out of 5 average rating, 11 reviews

Nana's House

4.94 out of 5 average rating, 17 reviews

2-Floor 2-bedroom Harbor View

Private room in South Boston

A spacious bedroom features a dark wood bedframe with a light blue bedding set. A ceiling fan is visible above, and a television is positioned on a wooden dresser. Artwork adorns the walls, and a basket is placed in the corner next to a bedside table.

Large Private Bedroom & Bathroom by the Seaport

4.87 out of 5 average rating, 695 reviews