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House vacation rentals in South Boston

Find and book unique houses on Airbnb

Top-rated house rentals in South Boston

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A living room corner features a modern television on a wooden stand near a traditional fireplace, which includes a sleek black mantel. Art adorns the wall above the fireplace, while natural wood flooring creates a warm and inviting atmosphere.
Home in Somerville
4.97 out of 5 average rating, 324 reviews

Best House Cambridge/Somerville

spacious 1900's mansard Victorian. Bright cheerie & centrally located if you're looking for a pad in Cambridge/Somerville. A 10-12minute walk to Harvard Square & close to the Red Line. Great kitchen, living room & /cablewifi. Three bedrooms--one with a European Queen Bed, one double bed & one single. There is one full bathroom w/a large glass shower & a claw foot tub. There is a half bath on the first floor. There is a front porch to sit & sip wine on & a back deck where you can grill & eat out on. I've been living here 12 years--Its tastefully appointed, eclectic finds & a mid century modern touch--absolutely the best equipted kitchen. I've been a chef in Boston & Cambridge for quite some time!

Top guest favorite
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
4.99 out of 5 average rating, 226 reviews

Family Friendly City Oasis! 2 Free Parking Spots!

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

Top guest favorite
A warm living area features a brown leather sofa accompanied by two striped chairs. A rustic table stands in the center, while a colorful area rug covers the floor. An artwork hangs on the wall, and a 'Boston' sign adds character to the space.
Home in West Roxbury
4.99 out of 5 average rating, 273 reviews

The Red Door Carriage House

The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

Top guest favorite
A welcoming living area features a gray sofa and a green couch, complemented by a patterned area rug. A television sits on a stand against the wall, while indoor plants add a touch of greenery. Natural light illuminates the space from well-placed ceiling lights.
Home in Newton
4.95 out of 5 average rating, 161 reviews

Newly Renovated Lovely 2 bedroom unit - Newton MA

Only a 10 minute drive to the heart of Boston's downtown area and other central Boston colleges and universities. This is a newly renovated 2 bedroom unit with 2 bathrooms on the first floor for parties up to 7 people (convertable couches) in a quiet and peaceful Irish suburban community. Driveway and street parking is always available. About an 11 minute walk to the nearest commuter rail line. Laundry access in the basement. No indoor smoke and no open flames, fines will be issued if caught.

Guest favorite
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 South End
4.95 out of 5 average rating, 188 reviews

Charming South End Farmhouse - Near Northeastern!

Charming 3-bedroom, 2.5-bathroom house located in Boston's vibrant South End! Our cozy and dog-friendly home has a private patio, dining area, a fully equipped kitchen, 1G Fiber wifi and sleeping accommodations for up to 7 guests. Perfect for families or larger groups! Featuring two TV's with streaming and essentials like fresh linens, towels, toiletries, extra pull out trundle couch. Just a short walk from Northeastern University, walkable to Fenway Park and a <5 minute walk to the T!

Guest favorite
A well-equipped kitchen features dark cabinetry and a spacious island. Stainless steel appliances, including a gas range and dishwasher, are present. Natural light fills the room through the window, highlighting the polished wood floor and the modern fixtures throughout the space.
Home in Roxbury
4.98 out of 5 average rating, 140 reviews

Spacious Boston Retreat for Families & Groups

Welcome to your spacious and fully furnished 5-bedroom home in Boston—a harmonious blend of classic charm and modern comfort. Spanning over 3,000 square feet, this beautifully restored retreat is perfect for families, groups, and business travelers. Situated just minutes away from top universities, medical centers, and iconic attractions, the home offers convenient amenities such as free parking, fast Wi-Fi, and ample living space for relaxation, work, or exploring the city with ease.

Guest favorite
A bright living area features a plush blue sofa adorned with a light throw blanket, complemented by a glass coffee table. Natural light filters through sheer curtains, illuminating the space. A stylish armchair and a dining area with a wooden table are visible in the background.
Home in Dorchester
4.96 out of 5 average rating, 137 reviews

LargeDuplex10Beds w/prkg near Downton

Blending modern conveniences with historic charm, this newly renovated duplex features 5 bedrooms/2 bathrooms. Open space kitchen-living room, 55"Roku TV. Free Wifi. Free Laundry 8mns to Beach Free Street Parking 4.6 miles to Downtown, Convention. Perfect for large groups Close to major Universities. 8 Minutes walk to train Free coffee/tea, toaster, blender. Free linens, towels. 10 mns to Dorchester brewing, South Bay center & beach. We love and look forward to hosting you.

Top guest favorite
The living room features a crimson couch paired with patterned armchairs, arranged around a central coffee table. The space is enhanced by natural light from large windows with shutters. Decorative plants are positioned nearby, contributing to a cozy and welcoming environment.
Home in East Boston
4.98 out of 5 average rating, 205 reviews

Boston Best with Parking - GREAT reviews

**READ our reviews :) - 10min walk to Airport Blue line subway T-stop - 10min drive to Downtown Boston - Local dining options in walking distance - 1 parking spot available upon request - Spacious and comfortable house Welcome to your Best Boston experience. I am Rafael and I will ensure that you get any attention needed with a text, call, or email. We hope that you enjoy our recommendations for activities and meals - we based them on our lifelong East Boston experiences.

Guest favorite
Home in Malden
4.91 out of 5 average rating, 199 reviews

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Top guest favorite
A living room area features a striped couch in shades of green and cream, positioned in front of a wooden coffee table with a television atop it. A framed painting of a ship hangs above a decorative fireplace, while built-in shelves add a touch of storage and display.
Home in Charlestown
4.81 out of 5 average rating, 202 reviews

Getaway in Historic Charlestown

**PLEASE NOTE REGARDING PARKING" Resident sticker parking 8 am to 8 pm Monday thru Friday. Weekends and holidays, no restrictions. The automobile has to be registered in Charlestown to get a parking sticker. The first floor of a three-story wooden framed home, built-in 1875. A totally private space. There is a good-sized living room, a bedroom with a queen size sleigh bed, and a full kitchen. The 'cozy' bathroom was added in 2012. Maximum of TWO people.

Guest favorite
A spacious living area features a mix of comfortable seating, including a large sofa and a cozy armchair. Natural light streams through multiple windows covered with woven shades. Shelves filled with books and decorative items line one wall, while a light-colored rug adds warmth to the concrete floor.
Home in Brookline
4.92 out of 5 average rating, 164 reviews

Pretzel Factory Loft w/Peloton

Creative loft style house that is home to a fashion designer and her family! Two floor loft like living very centrally located in Brookline MA. Very centrally located in Brookline Village. A few minutes walk to the T and very close to the hospital district. Whole house perfect for the whole family with fast Wifi and garage parking. Search for 'Everywhere Architecture' & click on 'White Place' to see more pictures!

Top guest favorite
Home in Swampscott
4.93 out of 5 average rating, 108 reviews

Oceanfront I Decks I 4 Ensuite BRs I 35 min to Boston

🐚 Welcome to Egg Rock House - “Wicked awesome” oceanfront home on the scenic shores of New England. Steps to restaurants, shops, nightlife, trains, and endless outdoor fun. Perfect launchpad for visiting Ipswich, Newburyport, Salem, Marblehead, Gloucester, and Rockport. Only 30 minutes by train to Boston’s North Station. Relax on the front deck with sweeping ocean views just outside your door.

Popular amenities for South Boston house rentals

When is the best time to visit South Boston?

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Avg. priceﺩ.ﺇ 1,362ﺩ.ﺇ 735ﺩ.ﺇ 735ﺩ.ﺇ 1,653ﺩ.ﺇ 1,686ﺩ.ﺇ 1,836ﺩ.ﺇ 1,737ﺩ.ﺇ 1,653ﺩ.ﺇ 1,660ﺩ.ﺇ 1,653ﺩ.ﺇ 735ﺩ.ﺇ 1,315
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Quick stats about house rentals in South Boston

  • Total vacation rentals

    Explore 40 vacation rentals in South Boston

  • Nightly prices starting at

    South Boston vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 1,600 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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