Family-friendly holiday rentals in South Boston Waterfront

An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.

4.99 out of 5 average rating, 112 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!

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.

4.92 out of 5 average rating, 182 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.

4.95 out of 5 average rating, 147 reviews

A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.

Boat in Charlestown

2BR Spacious Yacht - Heat & AC- On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

4.89 out of 5 average rating, 682 reviews

A charming yellow Victorian house is framed by lush greenery and tall trees. The front porch features white railings and steps leading to the entrance, with plants adding a welcoming touch. Sunlight softly illuminates the exterior, highlighting the classic architectural details.

Flat in Dorchester

2 bedroom 1st Floor Apartment in Savin Hill

This is a private apartment: living room, one bedroom with a queen size bed and 2 single bed 'Castro Convertibles' and one bedroom with a single bed, bathroom, fully equipped eat in kitchen, back porch and yard. Excellent access to public transportation, downtown area, and tourist attractions. Also suitable for longer stays. One of your hosts is a nurse and we would be happy to host travel nurses. Very convenient to MGH and Longwood Medical area. Please let us know if you are interested.

A charming brick building is framed by lush green foliage. Large windows are adorned with flower boxes, displaying red flowers. A blue front door adds a pop of color while welcoming visitors to the entrance, which is highlighted by warm lighting.

4.87 out of 5 average rating, 110 reviews

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.

4.88 out of 5 average rating, 129 reviews

A modern living area showcases a grey sectional sofa, complemented by a geometric area rug. A small coffee table sits in front, and a desk with a chair is positioned nearby. Large windows provide natural light, and a cityscape photograph adorns the wall.

Flat in East Boston

1 BR Gem 5min to Train & Airport explore the city

This modern stylish place to stay is perfect to explore the city of Boston. It’s a hidden gem 1 block away from the Blue Line T station, two stops away from downtown, the aquarium, TD Garden, Faneuil Hall, and multiple museums. 2 mins walking distance from the apartment to Piers Park and spectacular views of Boston Harbor and the skyline.Hop on the ferry to explore Seaport restaurants and bars close by with differing cultures and cuisines. Only 2 min from Logan Airport via train or car.

Apartment in South Boston

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.

4.95 out of 5 average rating, 120 reviews

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!

Guest suite in South Boston

The exterior of a charming historic home is displayed, featuring pink shingle siding and white trim. Window boxes with flowers and small American flags adorn the windows, creating a festive and welcoming atmosphere, alongside patriotic decorations draped beneath each window.

4.96 out of 5 average rating, 445 reviews

Paul Revere Suite PVT Entry/BATH QN Bed History

*5 STAR ★★★★★ **No Chores! No To-Do List!** Yes, Private Bathroom! Cleaned and Sanitized *Luxury and Comfort *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *National Historic Sites *Dedicated Luxury Suites *Key-less Coded Access *Queen Pillow Top Bed *Private bath with shower *Great Bath Amenities *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking.

4.94 out of 5 average rating, 171 reviews

A cozy living space features exposed brick walls complemented by warm wooden accents. A spacious sectional sofa is arranged around a circular coffee table, adorned with a vase of flowers. Nearby, framed artwork is displayed on the wall, adding character to the room.

Flat in East Boston

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!

4.94 out of 5 average rating, 198 reviews

A modern kitchen is showcased with light wood cabinetry and an expansive island featuring a white marble countertop. Pendant lights hang above, illuminating the space. The open layout leads to a cozy living area with a large sectional sofa, surrounded by windows that invite natural light.

Apartment in East Boston

Luxury apt w/ sauna & deck | by airport, downtown

Welcome to your private oasis just minutes away from Logan Airport AND Boston's bustling streets. Start your day with a walk along the water, then enjoy all that Boston has to offer right nearby. 1 min. walk to the waterfront 5 min. walk to Logan Airport 10 min. Uber (or 1 MBTA stop) to Downtown Boston PARKING IS DIFFICULT: - If you’re coming during the week, parking can be hard to navigate - If you MUST bring a car, do not arrive in the evening or you may not find a spot

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, 244 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

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.

4.89 out of 5 average rating, 178 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.

Popular amenities for South Boston Waterfront family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The kitchen features modern cabinetry and high-end stainless steel appliances, including a refrigerator and microwave. A dark countertop extends to a breakfast bar with two white stools. Warm hardwood floors and soft overhead lighting create an inviting cooking space.

4.92 out of 5 average rating, 75 reviews

South Boston. Minutes away from Convention Center

4.92 out of 5 average rating, 216 reviews

Flat in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

4.92 out of 5 average rating, 131 reviews

A modern kitchen is showcased, featuring gray cabinetry and a large island with seating for four. Stainless-steel appliances are integrated seamlessly, while light reflects off the marble countertops. A dining area is visible in the background, with natural light filtering through a window.

Apartment in Brighton

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Superhost

A small dining area is shown with a sleek black table and three high-backed chairs. Natural light filters in through two windows, providing a bright ambiance. A wooden bench is positioned against the wall, contributing to the room's functional layout.

Apartment in Cambridgeport

4.75 out of 5 average rating, 123 reviews

1 BR full apt w/ private hot tub, yard; sleeps 4

4.96 out of 5 average rating, 266 reviews

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Flat in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

Guest suite in Lakeside Marblehead

5 out of 5 average rating, 54 reviews

Headers’ Haven

Superhost

A modern open-concept living space features a well-equipped kitchen with stainless steel appliances and a large island with seating for five. A cozy living area displays a sectional couch facing a wall-mounted TV, with large windows allowing natural light to brighten the room.

Home in South Boston

4.93 out of 5 average rating, 107 reviews

Heart of Southie - Hot Tub + Walk to Top Bars

4.98 out of 5 average rating, 207 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Flat in Arlington

Lakeside apartment, patio, hot tub, outside shower

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 152 reviews

A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.

Apartment in Bay Village

Condo in downtown Boston

4.99 out of 5 average rating, 216 reviews

The kitchen features white cabinetry and stainless steel appliances, with a spacious layout for cooking. A game table is shown with a pool table in the background. A cozy living area includes a light blue accent wall and comfortable seating. The backyard displays a grassy area with a slide and a playset.

Home in South Boston

Family Friendly City Oasis! Free Parking, King Bed

4.88 out of 5 average rating, 232 reviews

A well-lit studio features a spacious bed adorned with colorful throw pillows. A small television sits on a stand opposite the bed. Wall-mounted shelves display framed art and decorative items, while large windows allow natural light to fill the room.

Flat in South End

Super location! One free parking spot! Walk Walk!

Superhost

Flat in West End

4.76 out of 5 average rating, 127 reviews

(42L5) Celtics Bruins TD Garden Outside your door!

4.83 out of 5 average rating, 250 reviews

A private patio features two hanging egg chairs adorned with green patterned cushions, positioned on a wooden deck. A small round planter sits in the center, adding a touch of greenery. The backdrop showcases urban buildings with a clear blue sky above.

Flat in Back Bay

(N2R) Private Deck, Styled Studio, Prime Location!

4.87 out of 5 average rating, 251 reviews

A modern living area features a light-colored sectional sofa and two patterned chairs arranged around a small table. A wall-mounted television is positioned above a sleek fireplace, surrounded by built-in shelving displaying decorative items. Natural light filters through sheer curtains.

Home in East Boston

Tribeca chic | 2 BR w/private patio

4.98 out of 5 average rating, 281 reviews

A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.

Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

4.94 out of 5 average rating, 158 reviews

A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.

Flat in Nahant

Ocean view studio with hot tub & access to Boston

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 32 reviews

A motor yacht is docked at a marina, featuring a spacious upper deck with a canopy. The exterior showcases a cream-colored hull with large windows and a comfortable layout. A wooden walkway leads to the boat, surrounded by additional boats in the marina.

Boat in Charlestown

Serenity - 36’ Aft Cabin Carver

4.97 out of 5 average rating, 65 reviews

An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.

Home in Norwood

the house of id; vintage shop, accessible space

4.97 out of 5 average rating, 110 reviews

Home in Weston

Spacious vacation unit in premium suburban town

4.88 out of 5 average rating, 104 reviews

A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.

Guest suite in Rockland

Cozy Private Suite halfway between Cape & Boston

Guest house in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

4.95 out of 5 average rating, 207 reviews

Country Cottage in the City

4.93 out of 5 average rating, 69 reviews

A vibrant outdoor pool area features a clear blue pool surrounded by a spacious patio. Lounge chairs are neatly arranged alongside the pool, with manicured shrubs and flowers adding color to the landscape. A privacy fence partially encloses the space, creating a secluded atmosphere.

Home in Waltham

Quiet/Private Neighborhood

4.97 out of 5 average rating, 406 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Flat in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!