Family-friendly holiday 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.

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 spacesFamilyLocation

4.97 out of 5 average rating, 584 reviews

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!

KitchenFamilyCheck-in

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.

FamilyIndoor spacesOutdoor spaces

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, 116 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.

KitchenFamilyAmenities

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.

4.96 out of 5 average rating, 136 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!

FamilyKitchenComfort

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.

4.89 out of 5 average rating, 150 reviews

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 spacesFamilyLaundry

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

Indoor spacesFamilyCondition

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.

FamilyIndoor spacesAccuracy

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.

4.84 out of 5 average rating, 157 reviews

Right Near Convention Center and Train Station

Newly renovated first floor unit. A few blocks from the Boston Convention Center and right next to the Broadway red line train station. Updated two bedroom, one full bath, washer, dryer, brand new kitchen, central air conditioning, stainless steel appliances, limited parking spots but plenty of street parking. This is a really nice place conveniently located in South Boston. Very close to Logan airport, Flynn Cruise Port and everything in Seaport and downtown.

KitchenFamilyParking

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!

Indoor spacesFamilyParks

An open kitchen-living area features a large central island with dark cabinetry and a light countertop. Stylish pendant lights hang above the island. A comfortable seating area is visible, with natural light filtering through large windows and doors that lead to an outdoor space.

4.97 out of 5 average rating, 148 reviews

Perfectly Renovated Home w/ Private Outdoor Oasis

COMPLETELY PRIVATE - NO SHARED SPACE OTHER THEN WASHER/DRYER AREA IN BASEMENT! Enjoy a private kitchen, 2 bedrooms, 2 baths and private outdoor space. The Master Bedroom has a king Bed with an ensuite bathroom. The Second Bedroom has a queen bed, gas fireplace and is right across from the second full bath. PARKING IS NOT INCLUDED. **outdoor furniture will be put away for the Winter in November & reassembled mid-May*

Indoor spacesFamilyCheckout

4.98 out of 5 average rating, 205 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.

KitchenIndoor spacesQuiet

Popular amenities for South Boston Waterfront family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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 spacesHot tub

4.96 out of 5 average rating, 285 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.

KitchenIndoor spacesAccuracy

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesFamilyLaundry

4.93 out of 5 average rating, 242 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 87 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

KitchenFamilyCondition

4.89 out of 5 average rating, 35 reviews

Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

FamilyKitchenView

5.0 out of 5 average rating, 16 reviews

Home in Medford

Hot tub - Arcade - Boston themed rooms

KitchenIndoor spacesBackyard

4.88 out of 5 average rating, 40 reviews

Home in Somerville

3BR Hot Tub Retreat, Fire Pit & Parking

FamilyKitchenCheck-in

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 173 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

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 105 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

KitchenIndoor spacesHospitality

4.96 out of 5 average rating, 423 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)

FamilyKitchenGetting around

4.93 out of 5 average rating, 208 reviews

A modern living area features a spacious sectional sofa with decorative pillows, facing an open kitchen fitted with sleek cabinetry and bar seating. Large windows provide natural light, while plants are displayed on shelves, enhancing the contemporary design.

Apartment in East Boston

Luxury Penthouse w/ Private Roof Deck By The Ocean

KitchenFamilyOutdoor spaces

4.99 out of 5 average rating, 241 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! 2 Free Parking Spots!

FamilyKitchenValue

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, 165 reviews

Southie Condo-By Subway-Bring Pets-Pool Table

Indoor spacesKitchenTV

4.94 out of 5 average rating, 225 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

Indoor spacesKitchenPets

4.78 out of 5 average rating, 150 reviews

Apartment in West End

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

KitchenIndoor spacesWalkability

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 116 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

KitchenFamilyDecor

4.8 out of 5 average rating, 124 reviews

Apartment in Brighton

The Drew : Vibrant • Comfortable • W/D • City View

KitchenIndoor spacesParks

4.94 out of 5 average rating, 257 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

KitchenIndoor spacesParking

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.

Country Cottage in the City

FamilyIndoor spacesAccess

4.95 out of 5 average rating, 218 reviews

4.87 out of 5 average rating, 209 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

Indoor spacesFamilyHospitality

4.99 out of 5 average rating, 168 reviews

Cottage in Marblehead

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

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 348 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

Indoor spacesKitchenShared spaces