Family-friendly vacation rentals in South Boston Waterfront

Guest suite in South Boston

A spacious sleeping area features a king bed with a plush white duvet and decorative pillows. Warm light is provided by bedside lamps, while a colorful rug adds texture to the wooden floor. A decorative door, showcasing a lighthouse scene, leads to another room.

4.97 out of 5 average rating, 583 reviews

One by Land BCEC History-Cruise- PVT Bath/Entry

*5 STAR ★★★★★ *Distinctive Suites **No Chores! No To-Do List!** *Sparkling Clean and Sanitized *Yes a Private Bathroom *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *Dedicated Luxury Suites *Key-less Coded Access *King EuroTop Bed *Edloe Finch Sofa *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking. Paid parking located at: 12 Drydock Ave, Boston, MA 02210

Indoor spacesFamilyWalkability

4.99 out of 5 average rating, 139 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!

FamilyKitchenComfort

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, 207 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.

KitchenFamilyParking

4.96 out of 5 average rating, 135 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!

Indoor spacesFamilyNearby

4.89 out of 5 average rating, 148 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

Indoor spacesFamilyLocation

4.95 out of 5 average rating, 156 reviews

An open-concept living area showcases a modern kitchen with white cabinets and stainless steel appliances. A dining table is positioned adjacent, with seating for four. Comfortable seating is provided by a light-colored sofa and stylish chairs, complemented by a textured area rug.

Condo in East Boston

Modern Luxury | Free Parking, Near T | Home Cinema

Discover a stylish East Boston condo featuring modern farmhouse design and stunning Boston skyline views. Just a 5-minute walk to the Blue Line and only 11 minutes from Logan Airport, it's the perfect home base for exploring the city. This spacious 3-bedroom retreat comfortably sleeps 7 guests and includes a luxurious home theater, a fully equipped kitchen, and free parking. Enjoy the perfect blend of comfort, convenience, and a quiet neighborhood just minutes from downtown Boston.

KitchenFamilyTV

4.97 out of 5 average rating, 100 reviews

The living room features a leather sofa and an armchair with light upholstery, arranged around a central ottoman. Natural light enters through the large windows, adorned with curtains. A small wooden table and a plant add to the inviting atmosphere, alongside a mounted television.

Home in South Boston

Beautiful Southie Single Family

Your whole family can enjoy this single-family rental in the heart of Southie. Five bedrooms with lots of room for families of all ages! This house is situated in a picture-perfect, calm, and quiet part of Boston but is centrally located a short walk from beaches, parks, shopping, and top-rated restaurants. Easy public transit connects you directly to the Back Bay, Seaport, or Downtown. Plus you can bring your car and park in our garage spot a 10 min walk from the front door.

KitchenIndoor spacesParking

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, 271 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

Indoor spacesKitchenHospitality

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.

4.87 out of 5 average rating, 208 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.

FamilyKitchenBiking

4.96 out of 5 average rating, 212 reviews

A scenic view of the city skyline is captured from a waterfront promenade, with bright sunlight reflecting off the water. A curved brick pathway leads towards the railing, showcasing the expansive skyline of modern buildings in the distance.

Apartment in East Boston

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!

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 257 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!

FamilyIndoor spacesSleep quality

A light-filled living area features large windows with leafy views. A beige sofa and a yellow armchair offer comfortable seating, while a wooden coffee table rests centrally on a soft area rug. A dining table for two is positioned beside the windows, showcasing a world map on the wall.

4.86 out of 5 average rating, 123 reviews

Cozy retreat w/ patio & backyard

Welcome to your private South Boston retreat on Telegraph Hill - a comfortable, self-contained apartment with a patio, full kitchen, and easy Red Line access. - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio w/ outdoor dining & sun loungers - Full kitchen w/ dishwasher, gas stove & coffee - 55" HDTV w/ Roku, workspace & high-speed Wifi - In-unit washer & dryer - pet-friendly - Self check-in | Crib available upon request

KitchenIndoor spacesLong stay

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

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, 114 reviews

Heart of Southie - Hot Tub + Walk to Top Bars

FamilyIndoor spacesHospitality

4.78 out of 5 average rating, 359 reviews

The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.

Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

FamilyIndoor spacesHeating

4.96 out of 5 average rating, 282 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.

Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

KitchenFamilyPool

4.98 out of 5 average rating, 219 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesKitchenDecor

4.92 out of 5 average rating, 237 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenFamilyCondition

5.0 out of 5 average rating, 86 reviews

A living area is presented with a blue futon, complemented by striped pillows. Two bright orange chairs are positioned beside a small black table. A light fixture with an arc design hangs above, illuminating the space. A door leads to an adjacent room.

Apartment in North End

Amazing Location in Little Italy with Roof Deck

FamilyKitchenView

4.92 out of 5 average rating, 25 reviews

Condo in Cambridge

Convenient 3 Bed - Steps to Kendall

FamilyIndoor spacesSleep quality

Guest suite in Marblehead

5.0 out of 5 average rating, 85 reviews

Headers’ Haven

FamilyKitchenBackyard

Family- and pet-friendly home rentals

Superhost

A bright living room features modern furniture, including two blue chairs and a gray couch. A dark round coffee table is centered on the polished wooden floor, with a decorative tray and magazines atop. Natural light enters through a window dressed with light curtains.

Condo in South Boston

4.85 out of 5 average rating, 155 reviews

Right Near Convention Center and Train Station

FamilyKitchenAccuracy

4.88 out of 5 average rating, 171 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.

Condo in Boston

Condo in downtown Boston

KitchenFamilyHeating

4.98 out of 5 average rating, 102 reviews

A welcoming living area features a marble-topped coffee table surrounded by comfortable seating. A decorative fireplace with a herringbone pattern adds warmth. Natural light filters through the space, highlighting a large mirror and a simple bouquet on the table. The kitchen is visible in the background.

Apartment in Charlestown

Designer 3-BR Apt in Historic Charlestown, Boston

FamilyKitchenGetting around

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, 115 reviews

City Sanctuary Private Terrace and Ocean Views

FamilyIndoor spacesLong stay

A pool table is centrally positioned in the living space, with a selection of colorful billiard balls arranged on its surface. Natural light enters through multiple large windows, illuminating the room. A cozy seating area is visible in the background, with a wood-burning fireplace and decorative shelving.

4.93 out of 5 average rating, 163 reviews

Southie Condo-By Subway-Bring Pets-Pool Table

Indoor spacesKitchenQuiet

4.96 out of 5 average rating, 420 reviews

A functional kitchen area is shown, featuring a corner layout with wooden cabinets and marble countertops. A double sink is positioned under the cabinet, while a white stove is situated next to a vintage wall clock. Fresh flowers are displayed in a vase on the counter.

Apartment in South End

Charming South End Duplex (Pets Ok)

Indoor spacesKitchenQuiet

4.94 out of 5 average rating, 221 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.

Condo in East Boston

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

KitchenIndoor spacesAmenities

Superhost

The exterior of a charming brick house is presented, featuring rounded corners and a dark front door. Large windows allow natural light to enter, while greenery adorns the adjacent wall. The inviting entrance is complemented by stone steps leading to the doorway.

Home in South End

4.95 out of 5 average rating, 200 reviews

Charming South End Farmhouse - Near Northeastern!

FamilyIndoor spacesAir conditioning

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 109 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 161 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Indoor spacesKitchenLayout

4.94 out of 5 average rating, 254 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

KitchenFamilyCondition

4.88 out of 5 average rating, 206 reviews

A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.

Guest suite in Revere

Amazing studio

FamilyKitchenQuiet

4.99 out of 5 average rating, 167 reviews

Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

FamilyKitchenCleanliness

4.97 out of 5 average rating, 346 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Private Suite• Pool • Sleeps 4 • Boston • Airport

KitchenIndoor spacesCondition

Guesthouse 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, 217 reviews

Country Cottage in the City

FamilyKitchenCheck-in