Vacation rentals with outdoor seating in South Boston Waterfront

4.99 out of 5 average rating, 203 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

4.95 out of 5 average rating, 151 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

Take in the beautiful skyline view as you have your morning beverage of choice, then take a relaxing stroll along the harbor walk 1 minute to the harbor 5 minute uber / 10 minute walk to airport 15 minutes to downtown Boston (by MBTA or uber) ON STREET PARKING: Only free 6P-8A and on the weekend. There is a $2.50 toll to drive into the city. Spot hero is a parking app that works great in Boston also. PARTIES: Not allowed. This is a family neighborhood. No loud music. Quiet hours after 9pm.

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, 159 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.

4.96 out of 5 average rating, 106 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

Peaceful suite in Boston with city views

Enjoy Boston in an elegant 2 bedroom/bath with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

4.95 out of 5 average rating, 110 reviews

Condo in Beacon Hill

Charming and Historic Apartment

Located in the heart of the historic Beacon Hill neighborhood, this cozy apartment is on the first two floors of a four-story brick townhouse. Tucked away on a European-style gated courtyard, the apartment is incredibly quiet and private, and only steps away from the shops, restaurants and public transportation of Charles Street and Cambridge Street. The well equipped kitchen has been recently renovated with free in unit laundry, bar, adjacent patio. Also WFH station and gas fireplace.

4.95 out of 5 average rating, 111 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 - 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!

4.95 out of 5 average rating, 984 reviews

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

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.

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, 122 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, 221 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, 141 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.

Condo 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, 169 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.

4.84 out of 5 average rating, 291 reviews

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.

Condo in East Boston

Stylish garden level studio with a private patio

Enjoy your stay in this stylish East Boston garden level studio with a private back patio. It is centrally located near restaurants, the waterfront, a running & biking trail, the airport, public transportation, and it is 1 metro stop away from downtown Boston. The metro stop, Maverick, is a 4 minute walk! The studio is equipped with a king bed that has a memory foam mattress, a queen pull out sofa, and a fully equipped kitchen.

Popular amenities for South Boston Waterfront outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.93 out of 5 average rating, 350 reviews

A cozy living room is highlighted by wood paneling and exposed beams. Plush seating includes a sofa and two armchairs. A coffee table is centered in the space, with a television displaying programming. Natural light fills the room through multiple windows adorned with soft curtains.

Home in Brighton

All the comforts of home, quiet city neighborhood

4.97 out of 5 average rating, 107 reviews

Home in Fort Hill

Spacious 5BR Boston Home • Near Fenway • Parking!

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 Roxbury

4.95 out of 5 average rating, 171 reviews

Charming South End Farmhouse - Near Northeastern!

4.93 out of 5 average rating, 105 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

4.93 out of 5 average rating, 274 reviews

A spacious living room exhibits rich green walls, complemented by warm wood flooring. Natural light streams through the slatted blinds, casting patterned shadows. Comfortable seating arrangements include a large couch and armchairs, with a wooden coffee table at the center and decorative artwork adorning the walls.

Home in Harvard Square

Harvard Square - free permitted on street parking

4.95 out of 5 average rating, 150 reviews

A spacious living area features a comfortable sectional sofa and a striped chair, accompanied by an ornate coffee table. Soft curtains frame double windows that allow natural light. A decorative painting above the fireplace complements the room's inviting decor.

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

4.86 out of 5 average rating, 213 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

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 420 reviews

A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.

Apartment in Salem

Winter Island Retreat

Apartment in Cambridgeport

A cozy bedroom is presented with a spacious bed covered in a textured blanket. Two bedside lamps provide soft illumination, while a large window offers a view of greenery. Dark curtains frame the window, enhancing the serene atmosphere.

4.96 out of 5 average rating, 144 reviews

Urban Oasis between MIT & Harvard

4.93 out of 5 average rating, 178 reviews

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

4.91 out of 5 average rating, 370 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.

Apartment in Newtonville

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

Superhost

A light gray living space features a comfortable sofa adorned with decorative pillows. A round coffee table sits in the center, complemented by a soft area rug. Two windows, including a skylight, provide natural light and views of the exterior.

Apartment in Everett

4.87 out of 5 average rating, 293 reviews

Huge 1BR w/King Bed near Airport, Boston, Salem

4.99 out of 5 average rating, 366 reviews

A living room features a fireplace surrounded by a brick wall, complemented by a cozy seating arrangement. Two armchairs and a sofa provide comfortable spaces for relaxation. Natural light enters through multiple windows adorned with lace curtains, illuminating the decorative rug underneath.

Apartment in Salem

House of Three Gables

4.83 out of 5 average rating, 489 reviews

A private deck is furnished with four sleek black outdoor chairs and a small table, offering a relaxing space. The view overlooks historic brick buildings, with greenery visible in the background, adding to the serene atmosphere.

Apartment in Chinatown

Private Deck! Parking for Rent. Heart of Boston.

4.97 out of 5 average rating, 126 reviews

The main entrance features a large, ornate door with intricate glass designs that allow natural light to brighten the foyer. An American flag is displayed beside the door, and a small planter with white flowers sits at the base of the steps.

Apartment in Salem

The 1870 Langmaid House Suite

Condo rentals with outdoor seating

4.87 out of 5 average rating, 133 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 Bay Village

Condo in downtown Boston

4.92 out of 5 average rating, 818 reviews

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.

Condo in Cambridgeport

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

4.93 out of 5 average rating, 219 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!

4.94 out of 5 average rating, 295 reviews

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

Beautiful, spacious South Boston Condo, Near T

4.96 out of 5 average rating, 311 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.

Condo in Salem

My Place - 2 Bedroom Condo with Parking

4.91 out of 5 average rating, 270 reviews

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.

Condo in Jamaica Plain

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

4.9 out of 5 average rating, 175 reviews

A modern kitchen features white cabinetry with a gray island and two black bar stools. Stainless steel appliances, including an oven and refrigerator, complement the light countertops. Pendant lights hang above the island, illuminating the space, while natural light streams through the window.

Condo in East Boston

Luxury Condo in Boston w/ backyard & parking