Vacation rentals with outdoor seating in South Boston

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Top-rated outdoor seating rentals in South Boston

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Dorchester

4.91 out of 5 average rating, 116 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Guest favorite

Home in South Boston

4.99 out of 5 average rating, 155 reviews

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

Guest favorite

Guest suite in Dorchester

4.96 out of 5 average rating, 226 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Guest favorite

Guest suite in Winchester

5 out of 5 average rating, 159 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Guest favorite

Condo in South Boston

4.95 out of 5 average rating, 266 reviews

Beautiful, spacious South Boston Condo, Near T

This beautiful townhouse is a 3 minute walk to the Andrew Square (subway) station that can take you to any where you want in Boston or the surrounding area. Museums, colleges, Fenway Park, TD Garden, the Common, Harvard Square, Faneuil Hall, Cape Cod, the Convention Center, Boston Harbor and various cruise ship terminals are many of the places you can visit. We are also a 15 min walk to Carson Beach. Although the place can sleep 6, we only allow 4 guests unless arrangements are made with host.

Guest favorite

Guest suite in Jamaica Central - South Sumner

4.92 out of 5 average rating, 213 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

Guest favorite

Condo in Dorchester

4.96 out of 5 average rating, 127 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

Guest favorite

Rental unit in Roslindale

4.98 out of 5 average rating, 249 reviews

Welcoming 2 Bedroom Apt, Steps from MBTA

If you're looking to just enjoy all that Boston has to offer or are here to celebrate a graduation, attend a sporting event, milestone birthday or anything else, we promise you this apartment will suit all of your needs. You can access the entire city while feeling cozy and content sipping your coffee or tea on the front or back porch decks. This second floor walk up is a 4 minute walk to the Forest Hill's Train Station and is minutes from a variety of restaurants and coffee shops.

Superhost

Rental unit in Fenway - Kenmore

4.84 out of 5 average rating, 231 reviews

Studio-Brigham Circle Longwood/HMS/BI/Dana Farber

Our cozy studio sits at the end of a quiet cul-de-sac with a patio and grassy backyard. Located just steps from Harvard Medical School and world-class hospitals (Brigham and Women's, Boston Children's, Dana Farber, Beth Israel, Mass Eye & Ear, etc.) and top colleges (Northeastern, Wentworth, MassArt, MCPHS, Simmons, Emmanuel, Berklee, NEC, etc). We are also located right on the green line T subway station and just a few stops away from all the attractions in downtown Boston.

Guest favorite

Rental unit in South Boston

4.96 out of 5 average rating, 157 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

Guest favorite

Condo in Roxbury

4.93 out of 5 average rating, 285 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!

Superhost

Rental unit in Beacon Hill

4.81 out of 5 average rating, 263 reviews

Beacon Hills Studio next to State house 3

Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.Take it easy at this unique and tranquil getaway.