Condo vacation rentals in South Boston

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Top-rated condo rentals in South Boston

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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, 300 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 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, 157 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

Top guest favorite
Condo in Beacon Hill
4.96 out of 5 average rating, 119 reviews

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.

Guest favorite
A modern kitchen features white cabinetry with glass doors and open shelving. A spacious island with seating for four is highlighted, along with a sleek sink and contemporary faucet. Glassware and a wine bottle rest on the countertop, enhancing the functional design.
Condo in Charlestown
4.92 out of 5 average rating, 393 reviews

Luxurious Home in Boston's Historic Charlestown

Featured in Boston Design Guide. Luxurious full floor condo in the historic and charming gaslight district of Boston's Charlestown section. Steps to Bunker Hill Monument and 1.5 miles from Encore Casino. Brand new kitchen with high end copper finishes, new appliances. HD Smart TV with movie and streaming apps. Queen size memory foam mattress, walk in closet, comfy pullout couch, full bathroom w/ newly tiled standing shower, washer/dryer and hotel-like amenities (shampoo, soap, etc.).

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, 113 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!

Superhost
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.
Condo in South Boston
4.87 out of 5 average rating, 120 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

Top guest favorite
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.
Condo in South End
4.94 out of 5 average rating, 244 reviews

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.

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 Fort Hill
4.94 out of 5 average rating, 340 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!

Top guest favorite
The living room features a dark sofa with teal accent pillows, complemented by a wooden coffee table. A light fixture hangs from the ceiling, and natural light fills the space through large windows. A small dining table with two chairs is visible, enhancing the cozy layout.
Condo in Beacon Hill
4.97 out of 5 average rating, 336 reviews

Gorgeous Beacon Hill 1BR | 1BA

Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

Top guest favorite
A pair of large, double doors with a rich, textured surface stands prominently in the background. The doors are flanked by warm, wooden floors and a light-colored sofa adorned with decorative pillows. A vibrant area rug adds color to the setting.
Condo in Downtown
4.97 out of 5 average rating, 184 reviews

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area-queen bed, also sofa in living room can become a pull-out queen size bed. There's also a side chair that converts to a chaise or a twin sleeper. The bathroom is with shower and tub, a complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

Top guest favorite
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.
Condo in South End
4.99 out of 5 average rating, 107 reviews

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.

Guest favorite
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
4.84 out of 5 average rating, 294 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 condo rentals

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Quick stats about condo rentals in South Boston

  • Total vacation rentals

    Explore 40 vacation rentals in South Boston

  • Nightly prices starting at

    South Boston vacation rentals start at € 43 per night before taxes and fees

  • Verified guest reviews

    Over 2,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 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

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