Holiday rentals with outdoor seating in South Boston

4.99 out of 5 average rating, 210 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

Welcome to The Southie House! An epic private home for a family vacation or conference in the Heart of Boston! Close to the Red line T for access to downtown, Cambridge & local universities, and short ride to the BCEC. At the same time a short walk to the beach for relaxing. Enjoy the back yard oasis with the whole group! This home provides you with a private place to relax after a full day of exploring, ensuring you have all the comforts of home while traveling. COME SEE OUR NEW GAME-ROOM & GYM

4.96 out of 5 average rating, 268 reviews

A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.

Guest suite in Ashmont

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Apartment in South Boston

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, 303 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.

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, 169 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.

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, 115 reviews

Boston Townhouse - 3bd / 2.5ba - Central Location

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!

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.

4.94 out of 5 average rating, 129 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!

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, 233 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

4.98 out of 5 average rating, 144 reviews

A living area displays a light-colored sofa adorned with patterned pillows, accompanied by two blue armchairs. A sleek work desk and a television are positioned near an elegant marble fireplace. Natural light fills the room, highlighting the wooden flooring and soft color palette.

Apartment in Charlestown

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. Luxurious KING sized bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

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, 175 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.

4.94 out of 5 average rating, 341 reviews

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.

Apartment in Fort Hill

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!

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, 109 reviews

City sanctuary - garden terrace - ocean view

Large sunny, private studio with stunning views and terrace overlooking the ocean, garden and JKF library, across the street from famous historic park Dorchester Heights. 2 blocks from beach. Close to convention center, airport, downtown, bus and trains. Easy walk to great local shops and haunts! Unit now equipped with Forbes #1 vetted best mattress - the Nectar Premier Hybrid Copper Queen mattress and there is a full size pull out futon

4.83 out of 5 average rating, 195 reviews

An outdoor patio is furnished with a round black metal table surrounded by four wicker chairs, each with cushion accents. A large red umbrella provides shade. Decorative potted plants enhance the green space. A spiral staircase and a wall covered in greenery are visible in the background.

Flat in Dorchester

3BR JFK/UMASS redline T+parking

*3BR at the 1st fl. in a 2-family house with a dining kitchen. *On request, guests can use the driveway free of charge *Free WIFI *8min walk: JFK/UMASS-3 T stops to Downtown *15 min walk to Beaches *15min drive to Airport * 6min walk: South Bay-Shopping Center: Stop&Shop & stores & restaurants *Check-in 3pm & Checkout at 10am

Popular amenities for outdoor seating rentals in South Boston

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 238 reviews

A charming house is nestled among trees, featuring a light-colored exterior with dark accents. An American flag is displayed outside. The front yard is landscaped with a stone wall and greenery, creating a serene setting. A gravel path leads to the entrance.

Home in Dedham

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

4.93 out of 5 average rating, 107 reviews

A light-filled dining area features a round white table surrounded by six white chairs. A modern light fixture hangs above the table, and a large mirror reflects the space. Natural light streams through the two windows, illuminating a decorative rug on the polished wooden floor.

Home in Jamaica Plain

Beaut private close univ+hospital

4.95 out of 5 average rating, 158 reviews

Home in Woburn

Stone Cottage with meadow view

4.98 out of 5 average rating, 151 reviews

An outdoor deck features two ornate chairs and a small table, overlooking a serene sunset. The horizon displays soft hues of orange and blue, with the silhouette of rooftops adding depth to the scene. Lush greenery can be observed nearby.

Home in Somerville

The Nest | A peaceful retreat in the city

4.78 out of 5 average rating, 223 reviews

A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.

Home in East Boston

Renovated Cozy City Getaway

4.87 out of 5 average rating, 228 reviews

The kitchen area features a modern design with a sleek, round dining table surrounded by four transparent chairs. Stainless steel appliances, including a refrigerator and stove, are present, complemented by wooden cabinetry. Natural light enters through a window, illuminating the polished hardwood floor.

Home in Brighton

Comfortable house w garden and parking, close to T

4.83 out of 5 average rating, 430 reviews

The bedroom features a spacious bed with a soft gray throw draped across it. A wooden dresser sits against the wall, complemented by a flat-screen TV. A small desk by the window offers natural light, while fresh flowers in a vase add a touch of color.

Home in Cambridgeport

City Oasis |Yard |Walk To Harvard MIT Train

4.87 out of 5 average rating, 247 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

Apartment rentals with outdoor seating

Flat in Lakeside Marblehead

An inviting outdoor deck features a seating arrangement with matching dark wicker chairs and a lounge chair, surrounded by vibrant flower pots. The entrance is framed by a dark door, and large windows allow natural light to brighten the space.

4.96 out of 5 average rating, 311 reviews

Charming & Private Marblehead Suite

4.89 out of 5 average rating, 531 reviews

The kitchen showcases dark wood cabinetry paired with granite countertops, featuring a stainless steel refrigerator and oven. A mosaic backsplash adds a touch of color, while a table with a floral tablecloth provides a casual dining space. Natural light floods the area through the window.

Flat in Revere

-2 Traditional 3 BR/2 Bath/Prkng By Arprt/Bos

Superhost

A spacious living area is highlighted by a comfortable sectional sofa adorned with a throw blanket. A television is positioned on a dresser across from the seating. A small dining table with two chairs is situated near a window, enhancing the natural light in the room.

Flat in Prospect Hill

4.92 out of 5 average rating, 356 reviews

Close to Harvard, MIT & Boston, Gym and Patio!

4.89 out of 5 average rating, 230 reviews

A cozy sleeping area features a spacious bed with a light-colored patterned bedspread. Bedside tables with lamps are situated on either side. A piece of wall art displaying floral designs is located above the bed. The floor is covered with wooden planks.

Flat in Somerville

Spacious, private apartment in perfect location

Superhost

The kitchen area features modern appliances, including a stainless steel refrigerator and built-in microwave. A large island with a deep sink is complemented by three black bar stools. Open shelving displays glassware and decorative items, while under-cabinet lighting adds functional ambiance.

Flat in Fort Hill

4.92 out of 5 average rating, 100 reviews

Bright Brownstone Condo - Terrace+ParkView

4.91 out of 5 average rating, 376 reviews

A cozy bedroom features a spacious bed covered with a plush purple blanket. Light blue walls complement the room, while a wooden desk and chair provide a functional workspace. A framed artwork and a door leading to additional storage are also visible.

Flat in Newtonville

3rd FL Apt for 1-4 Guests 15 minutes from Boston

4.87 out of 5 average rating, 130 reviews

A spacious kitchen is defined by rich wooden cabinetry and countertops, featuring a stainless steel refrigerator and microwave. A wooden dining table with multiple chairs is arranged nearby. Soft lighting highlights the tiled floor and decorative backsplash, creating a functional cooking space.

Flat in Dorchester

Rare 3.5 bed apt, super location Boston, +parking

4.94 out of 5 average rating, 413 reviews

A living room is featured with hardwood floors and exposed brick walls, creating a cozy ambiance. A large TV sits atop a white media console. A comfortable blue chair with a patterned cushion provides seating, while a coffee table enhances the space. Artwork decorates the walls.

Flat in Chelsea

5 minutes to downtown. Charming. Clean. Cozy.

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 143 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

Apartment in Cambridgeport

A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.

4.92 out of 5 average rating, 839 reviews

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

4.97 out of 5 average rating, 322 reviews

A cozy living room features a gray sofa and a black leather chair, centered on a light-colored area rug. Two windows illuminate the space, complemented by light curtains. A wooden coffee table holds decorative items and a lamp, while a woven wall hanging adds texture.

Apartment in Salem

My Place - 2 Bedroom Condo with Parking

4.91 out of 5 average rating, 230 reviews

A spacious living area features tall ceilings and large bay windows allowing ample natural light. A comfortable sectional sofa is positioned around a glass coffee table, with two chairs nearby. A gas fireplace and modern entertainment system are highlighted, creating a welcoming environment.

Apartment in South End

South End 1800sqft 2BR Audiophile Paradise

Apartment in Jamaica Plain

A fully equipped kitchen features a spacious granite countertop with seating for four on elegant black bar stools. Natural light streams in from the nearby window, illuminating the fresh purple flowers arranged as a centerpiece.

4.91 out of 5 average rating, 278 reviews

Fully-Equipped 2nd Floor 1-Bed 1-Bath Apt

4.96 out of 5 average rating, 123 reviews

Apartment in Beacon Hill

Charming and Historic Apartment

Superhost

A studio space features a spacious bed with a memory foam mattress and a queen pull-out sofa. A modern kitchen is visible, complemented by a dining area with high stools. Natural light enters through a window, while artwork adds visual interest to the walls.

Apartment in East Boston

4.83 out of 5 average rating, 300 reviews

Stylish garden level studio with a private patio