Vacation rentals with outdoor seating in South Boston

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in South Boston

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Condo in South Boston
4.94 out of 5 average rating, 320 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.

Top guest favorite
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.
Apartment in South Boston
4.93 out of 5 average rating, 189 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.

Top guest favorite
A spacious living room is showcased with large windows offering natural light. Comfortable seating includes a light green sectional sofa and a white couch. A wooden coffee table sits atop a colorful area rug. A flat-screen television is mounted on the wall, providing entertainment options.
Condo in Dorchester
4.97 out of 5 average rating, 160 reviews

1st floor, free parking off street, 3 min to train

1BR private first floor condo that has it all. Suitable for families, vacationing, and remote work. *Please note we live on the 2nd Floor (separate entrance) - FREE PARKING off-street driveway for 1 vehicle - PUBLIC TRANSIT 2 short blocks from Red Line, downtown in 15 min - SMART HOME High Speed dedicated Wi-Fi, smart speakers and lighting - WALKERS PARADISE Walk score 91 , many bars & restaurants & conveniences - PARKS Savin Hill & Beach within 10 min walk, near Carson Beach & Harbor walk

Guest favorite
A modern kitchen features white cabinetry and stainless steel appliances. A large island with seating is positioned centrally, complemented by pendant lighting above. Natural light streams in through the nearby window, illuminating the sleek countertops and stylish backsplash.
Apartment in Dorchester
4.84 out of 5 average rating, 267 reviews

🎖The Ashmont Apartment | Close to Subway/Downtown

This unique 2 bed/2 bath apartment is brand new, along with all the furnishings and amenities. The unit includes 1 Queen + 1 Full size en-suite bedrooms. The unit is extremely clean and beautifully decorated. Only a 5 minute walk to Ashmont T station (red line), which takes you directly into Downtown Boston, Harvard, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Guest favorite
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.
Apartment in South Boston
4.88 out of 5 average rating, 113 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.

Guest favorite
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.
Apartment in South Boston
4.86 out of 5 average rating, 104 reviews

South Boston retreat w/ patio & full kitchen

Welcome to your private South Boston retreat on Telegraph Hill - a cozy apartment with a patio, a full kitchen, and everything you need to feel at home in the city. - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio, private backyard & private entrance - Full kitchen w/ GE gas stove, dishwasher & coffee maker - 55" HDTV w/ Roku, dedicated workspace & high speed Wifi - Free in-unit washer & dryer - long term stays welcome - Pet-friendly | Crib available on request | Red Line nearby

Top guest favorite
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
4.95 out of 5 average rating, 123 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!

Top guest favorite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 1,033 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Top guest favorite
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.
Apartment in South Boston
4.94 out of 5 average rating, 146 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!

Top guest favorite
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.
Apartment in South Boston
4.96 out of 5 average rating, 258 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

Guest favorite
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.
Apartment in South Boston
4.88 out of 5 average rating, 193 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.

Top guest favorite
The private rooftop deck features a shaded seating area with sectional sofas adorned with cushions. Potted plants add greenery, while views of neighboring buildings and trees are visible in the background under a partially cloudy sky.
Condo in Roxbury
4.94 out of 5 average rating, 350 reviews

Boston Rooftop Retreat

A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Popular amenities for South Boston outdoor seating rentals

When is the best time to visit South Boston?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$52,677 GYDG$55,813 GYDG$65,637 GYDG$56,440 GYDG$62,502 GYDG$64,801 GYDG$63,965 GYDG$63,547 GYDG$62,920 GYDG$63,129 GYDG$60,830 GYDG$57,485 GYD
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Quick stats about vacation rentals with outdoor seating in South Boston

  • Total vacation rentals

    Explore 60 vacation rentals in South Boston

  • Nightly prices starting at

    South Boston vacation rentals start at G$14,633 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of South Boston vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across South Boston rentals

  • 4.9 Average rating

    South Boston stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    South Boston's top spots, include Castle Island, Andrew Station, and Broadway Station