Apartment holiday rentals in South Boston

4.98 out of 5 average rating, 109 reviews

The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.

Apartment in Winthrop

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

4.95 out of 5 average rating, 126 reviews

The open-plan living area features large floor-to-ceiling windows filling the space with natural light. A combination of a leather sofa and a cozy white couch is accompanied by a glass coffee table. A sleek dining table is positioned beside the modern kitchen, showcasing granite countertops.

Apartment in Back Bay

Spacious, Sun~filled Brownstone in Heart of Boston

Welcome to your elegant, luxury condo quality 3 bed 3 bath in the HEART of Boston: 5-10 min walk to Boylston, Copley, Boston Commons, Newbury, Prudential, Back Bay, South End & etc! This expansive, sun-drenched duplex offers a tranquil residential vibe in the center of Boston. Admire the dreamy, modern decor of the open-plan living space & peaceful surroundings. Perfect for weekend getaway, business trip, staycation, work-from-home, or relaxing home base while exploring all Boston has to offer.

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, 317 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.

4.96 out of 5 average rating, 138 reviews

Apartment 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.

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, 121 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!

A modern kitchen and living area feature sleek appliances, light cabinetry, and a cozy sectional sofa. A dining table with chairs offers ample seating. Large sliding doors open to the private balcony, allowing natural light and views of greenery to fill the space.

4.88 out of 5 average rating, 137 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

4.94 out of 5 average rating, 249 reviews

A bright and airy living area features large windows with natural light streaming in. A white sectional sofa with a yellow decorative pillow faces a modern entertainment unit. The exposed brick wall adds character to the space, which is complemented by warm bamboo flooring.

Apartment in South End

SouthEnd Penthouse

Centrally located penthouse unit in the heart of Boston SouthEnd. Abundance of sunlight, spacious living area, and open kitchen will make your stay a unique and charming experience in a historically preserved area. Ideal to explore the local neighborhood restaurants or walk to Boston commons, the ballpark, downtown or Newbury Street. The neighborhood is historic to Boston with classical brick stone look and the place itself is quite a gem, very quiet and open dining+living room style.

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.

4.94 out of 5 average rating, 205 reviews

Luxury apt w/ sauna & deck | by airport, downtown

Welcome to your private oasis just minutes away from Logan Airport AND Boston's bustling streets. Start your day with a walk along the water, then enjoy all that Boston has to offer right nearby. 1 min. walk to the waterfront 5 min. walk to Logan Airport 10 min. Uber (or 1 MBTA stop) to Downtown Boston PARKING IS DIFFICULT: - If you’re coming during the week, parking can be hard to navigate - If you MUST bring a car, do not arrive in the evening or you may not find a spot

4.94 out of 5 average rating, 347 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 Roxbury

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!

4.98 out of 5 average rating, 149 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. KING 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.

4.99 out of 5 average rating, 111 reviews

A living area features a contemporary black sofa and two matching armchairs arranged around a round glass coffee table, all placed on a vibrant blue rug. A large artwork hangs on the wall, and a window allows natural light to enter the space.

Apartment in South End

1 Bedroom Apartment in Boston/South End

One bedroom condo on parlor level on quiet South End street. Convenient to all the restaurants, Back Bay, Financial District, Downtown. There are stairs leading to the building. Full size bed, full-size tub with shower in bathroom. Wi-Fi. Listing is for the full apartment. Two guests only. No one under 18. No visitors or parties. There is no street or designated parking. Best for one or two people visiting and enjoying the city.

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.

4.82 out of 5 average rating, 318 reviews

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 apartment rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Weekly apartment rentals

4.96 out of 5 average rating, 102 reviews

The modern kitchen features sleek stainless steel appliances and a spacious island with seating. Natural light fills the area from multiple windows, highlighting the granite countertops. A dining table sits within the open layout, creating an inviting space for meals.

Apartment in Medford

Modern, Spacious, Top Floor Condo in A++ Location!

5 out of 5 average rating, 203 reviews

The living area features a genuine leather sectional sofa facing a large smart TV on a white console. Natural light enters through two tall windows, illuminating the hardwood floor. A patterned area rug is placed beneath a coffee table, with decorative accents arranged thoughtfully.

Apartment in Downtown

Spacious 3BR | Downtown Boston | Historic Gem

Apartment in Fenway-Kenmore

The kitchen features modern cabinetry in a light finish, complemented by a white countertop and a turquoise backsplash. Stainless steel appliances are present, including a microwave, oven, and refrigerator. Natural light enhances the inviting atmosphere from a nearby window, while a green plant adds a touch of vibrancy.

4.9 out of 5 average rating, 126 reviews

2Bedroom - WALK to subway, hospitals, food, & more

4.97 out of 5 average rating, 344 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

4.93 out of 5 average rating, 134 reviews

Apartment in Brighton

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Apartment in Downtown Salem

A small workspace features a marble-top table accompanied by a white chair with a fur throw. The green wall displays a variety of framed artwork and a small chalkboard with the word 'Welcome.' A mirror above the table reflects elements of the cozy room.

5 out of 5 average rating, 102 reviews

The Merchant's Carriage House - Downtown Salem

Apartment in Porter Square

A tranquil bedroom features a spacious bed dressed in neutral linens, flanked by matching bedside tables with lamps. A work desk made of light wood is positioned against the wall, accompanied by a cozy blue pouf. Natural light is softly diffused through a window covered by light curtains.

4.96 out of 5 average rating, 161 reviews

Harvard / Porter Square Apartment, 2brm + sofabed

4.84 out of 5 average rating, 418 reviews

A modern living space is presented with bright walls and stylish furnishings. A large dining table is positioned in the foreground, surrounded by dark chairs. The seating area features a light-colored sofa and an accent chair, complemented by artwork and a decorative wall-mounted antler.

Apartment in Salem

Modern Farmhouse Condo Near Downtown Salem

Pet-friendly apartment rentals

4.88 out of 5 average rating, 157 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 Boston

Condo in downtown Boston

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.

4.93 out of 5 average rating, 243 reviews

Family Home + Near Downtown + Cool Backyard!

Apartment in Jamaica Plain

A welcoming living area features a dark sofa with a plush throw pillow, complemented by a glass coffee table and decorative area rug. In the background, a console table holds a bowl and art pieces. A floor lamp provides soft lighting, enhancing the space's comfort.

4.9 out of 5 average rating, 111 reviews

Leafy & Tranquil, Artist house. Easy access Boston

4.99 out of 5 average rating, 253 reviews

The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.

Apartment in Marblehead

Harbor View Suite

Apartment in Jamaica Plain

A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.

4.89 out of 5 average rating, 593 reviews

Historic JP Brownstone with Parking. Pets Welcome!

Superhost

A comfortable outdoor seating area is presented on a covered porch. The space features a sectional sofa and four wicker chairs arranged around a glass coffee table. Views of nearby buildings and a clear blue sky can be seen in the background, enhancing the serene environment.

Apartment in Somerville

4.83 out of 5 average rating, 253 reviews

Spacious, cozy home near Boston!

4.91 out of 5 average rating, 105 reviews

A spacious living area is highlighted by a bright blue sectional sofa and a circular coffee table. Natural light streams through the window, illuminating the light brown hardwood floor and soft area rug. A decorative plant sits on the coffee table, adding a touch of greenery.

Apartment in Cambridge

#4B, Walk to Harvard, MIT, Redline! Prime Location

4.76 out of 5 average rating, 257 reviews

A well-appointed bedroom features a spacious bed with a light duvet and coordinating cushions. Two windows are dressed with patterned curtains, allowing natural light to fill the room. Artwork adorns the walls, complemented by a small desk with a potted plant and a chair.

Apartment in North End

Gorgeous Huge Duplex 3 baths sleeps 6 Parking

Private apartment rentals

The entrance features two tall nutcracker figures, dressed in vibrant red and blue, flanking the door. Green garlands and a wreath decorated with red accents adorn the black exterior, which is complemented by potted plants and bright red flowers.

4.85 out of 5 average rating, 55 reviews

Eastie near the airport Great location

4.93 out of 5 average rating, 27 reviews

A bright living room is presented, featuring a light-colored sofa and two upholstered chairs with striped patterns. A wooden coffee table occupies the center, and the space is complemented by two pieces of wall art and a fireplace, providing a cozy ambiance.

Apartment in South End

Cozy South End Corner

Apartment in Davis Square

4.92 out of 5 average rating, 13 reviews

New 2BR/2BA LUXE Harvard & MIT w/Parking Red Line

Superhost

Apartment in Jamaica Plain

4.9 out of 5 average rating, 39 reviews

Luxe Boston Condo, Near T

4.93 out of 5 average rating, 246 reviews

A welcoming living room features a large white sofa facing a decorative wooden coffee table. Two armchairs are positioned near a window, with light filtering through sheer curtains. Potted plants add greenery, complementing the warm wood floors and classic ceiling fan.

Apartment in Roslindale

Spacious 5BR Condo w/parking near METRO

The kitchen features wooden cabinetry and stainless steel appliances, including a gas stove and a refrigerator. A window provides natural light, illuminating the hardwood floor. Counter space is available for meal preparation, creating a functional area for cooking.

4.91 out of 5 average rating, 86 reviews

Extended stays

A modern kitchen features sleek stainless steel appliances, including a large refrigerator and a gas stove. White cabinetry complements the dark countertops. A central island with seating and a doorway leads to a bright entrance, enhancing the open layout.

4.98 out of 5 average rating, 52 reviews

Sunny Southie Modern 2 Bedroom with Deck