Family-friendly holiday rentals in South Boston

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, 136 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!

FamilyKitchenView

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, 202 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.

KitchenFamilyTV

The living area includes a spacious wooden coffee table positioned between two comfortable armchairs and a sofa. A partially visible dining area is in the background, with wooden chairs surrounding a table. Natural light enters through the window, enhancing the warm wood tones throughout.

4.94 out of 5 average rating, 330 reviews

Beautiful, spacious South Boston Condo, Near T

This beautiful townhouse is a 3 min walk to the Andrew Square (subway) station that can take you to anywhere you want in Boston or the surrounding area. Museums, colleges, Fenway Park, TD Garden, the Common, Harvard Square, Faneuil Hall, Cape Cod, Salem, the Convention Center, Boston Harbor and cruise ship terminals are many of the places you can visit. We are also a 15 min walk to the local beaches. Although the place can sleep 6, we only allow 4 guests unless arrangements are made with host.

KitchenIndoor spacesWi-Fi

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

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.

FamilyIndoor spacesAccess

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, 147 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 spacesFamilyAmenities

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, 133 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!

Indoor spacesFamilyLocation

Guest suite in South Boston

A spacious suite features a king EuroTop bed adorned with decorative pillows. A gray sofa with colorful accent pillows and a dark coffee table complement the room. Natural light enters through two windows, with light-colored curtains framing them. An eclectic rug adds warmth to the wooden floor.

4.96 out of 5 average rating, 551 reviews

Two by Sea BCEC Cruise History Pvt Bath/Entry King

* *5 STAR ★★★★★ **No Chores! No To-Do List!** *Yes a Private Bathroom *Sparkling Clean and Sanitized *Historic and Charming home *Luxury and Comfort *South Boston trendy neighborhood. *Dedicated Luxury Suite *Key-less Coded Access *King EuroTop Bed *Sitting area with 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

FamilyIndoor spacesBiking

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, 160 reviews

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!

KitchenIndoor spacesNearby

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, 267 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 spacesKitchenView

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, 206 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.

Indoor spacesKitchenNearby

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.

4.86 out of 5 average rating, 152 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.

FamilyKitchenBackyard

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, 119 reviews

Cozy 1BR retreat w/ backyard & patio

Welcome to your private South Boston retreat on Telegraph Hill - a self-contained apartment with a patio, full kitchen & in-unit laundry, steps from great dining & the Red Line. - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio, backyard & entrance w/ keypad self check-in - 55" HDTV w/ Roku & dedicated workspace - Full kitchen w/ dishwasher, GE gas stove & coffee maker - In-unit washer & dryer - pet-friendly - Walk to Seaport, dining & Red Line

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Popular amenities for South Boston family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 114 reviews

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

Heart of Southie - Hot Tub + Walk to Top Bars

FamilyKitchenComfort

4.96 out of 5 average rating, 281 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.

FamilyIndoor spacesCheck-in

4.98 out of 5 average rating, 217 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.

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesKitchenGetting around

4.92 out of 5 average rating, 235 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

FamilyKitchenDecor

4.78 out of 5 average rating, 358 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!

Indoor spacesKitchenValue

Guest suite in Marblehead

5.0 out of 5 average rating, 81 reviews

Headers’ Haven

FamilyKitchenHospitality

5.0 out of 5 average rating, 84 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

FamilyIndoor spacesNearby

4.72 out of 5 average rating, 135 reviews

Guest suite in Canton

Newly renovated, close to Foxboro and Boston

FamilyIndoor spacesShared spaces

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 238 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!

Indoor spacesFamilyCheck-in

4.92 out of 5 average rating, 287 reviews

Apartment in South End

Super location! 1st Floor! Walk everywhere!

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Guest suite in Jamaica Plain

A secluded patio area is visible, featuring a brick pathway and two metal chairs positioned for relaxation. The entrance to the guest unit is framed by a set of steps, accompanied by leafy trees that provide shade and a sense of serenity.

4.94 out of 5 average rating, 120 reviews

Peaceful Garden Apartment

FamilyKitchenQuiet

4.99 out of 5 average rating, 237 reviews

Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

KitchenFamilyCleanliness

Guest suite in Jamaica Plain

A cozy bedroom features a spacious bed with neutral bedding, flanked by bedside lamps. Skylights illuminate the room, highlighting the hardwood floors and a large area rug. A small seating area is present to the left, and a door leads to the exterior.

4.95 out of 5 average rating, 186 reviews

Skylit Suite in Musical home, easy access Boston

FamilyIndoor spacesComfort

4.92 out of 5 average rating, 1396 reviews

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

Guest suite in Winthrop

Licensed Boston airport studio 5 stars, subway

KitchenFamilyDecor

4.88 out of 5 average rating, 150 reviews

A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.

Apartment in Woburn

Newly Finished Guest Haven in Woburn

Indoor spacesKitchenLayout

4.94 out of 5 average rating, 253 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

KitchenFamilyDecor

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 101 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyKitchenCheck-in

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, 215 reviews

Country Cottage in the City

KitchenIndoor spacesHospitality

4.87 out of 5 average rating, 106 reviews

Apartment in Brighton

The Weiss : Modern Gallery • Historic Property!

Indoor spacesFamilyComfort

4.88 out of 5 average rating, 204 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

FamilyKitchenAccess

4.97 out of 5 average rating, 344 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 spacesSleep quality

4.99 out of 5 average rating, 163 reviews

Cottage in Marblehead

Pool Is Open! Steps from Harbor + Walk to Old MHD

FamilyIndoor spacesParking

4.97 out of 5 average rating, 443 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.

Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

FamilyIndoor spacesBackyard