
Holiday rentals with outdoor seating in South Boston Waterfront
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Top-rated rentals with outdoor seating in South Boston Waterfront
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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

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.

Top Floor luxury Condo
Kick back and relax in this calm, stylish space with skyline views of Boston. This sun filled top floor condo is fully equipped for short- or long-term rentals. This spacious 850sq foot apartment features one bedroom with a queen size bed, dresser and spacious closets throughout. A workspace with high speed 800BPS internet and stylish furnishings throughout. A full kitchen features gorgeous marble counter tops and high-end appliances. Off-street parking - small and medium cars only. Rear patio

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.

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.

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!

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.

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, fireplace, fully equipped kitchen & priv 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 the house and NO smoking in courtyard. Not suitable for children under 6 years old.

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!

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

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.

City sanctuary - garden terrace - ocean view
Large sunny, private studio with stunning views and terrace overlooking the ocean, garden and JKF library, across the street from famous historic park Dorchester Heights. 2 blocks from beach. Close to convention center, airport, downtown, bus and trains. Easy walk to great local shops and haunts! Unit now equipped with Forbes #1 vetted best mattress - the Nectar Premier Hybrid Copper Queen mattress and there is a full size pull out futon
Popular amenities for outdoor seating rentals in South Boston Waterfront
House rentals with outdoor seating

All the comforts of home, quiet city neighborhood

Charming South End Farmhouse - Near Northeastern!

Cheerful 1-bedroom New England Ranch

Harvard Square - free permitted on street parking

Renovated Cozy City Getaway

Tribeca chic | 2 BR w/private patio

City Oasis |Yard |Walk To Harvard MIT Train

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free
Apartment rentals with outdoor seating

Boston Brownstone

Mid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance

Hipster Basecamp | fireplace • views • parking

Couples Retreat - Apt in Charming Colonial Home

Urban Oasis near MIT & Harvard

Spacious, private apartment in perfect location

Oceanfront Pool. Close to Boston. Free Parking.

🎖The Ashmont Suite | Close to Subway + Downtown🎖
Apartment rentals with outdoor seating

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

Beautiful, spacious South Boston Condo, Near T

Newly Renovated Victorian close to Salem

My Place - 2 Bedroom Condo with Parking

South End 1800sqft 2BR Audiophile Paradise

Stunning South End 1BR - private roof deck

Stylish garden level studio with a private patio

Boston Rooftop Retreat
Quick stats about holiday rentals with outdoor seating in South Boston Waterfront
Total rentals
30 properties
Nightly prices starting at
$78 SGD before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Family-friendly rentals South Boston Waterfront
- Rentals with beach access South Boston Waterfront
- Fitness-friendly rentals South Boston Waterfront
- Rentals with pools South Boston Waterfront
- Rentals with a washing machine and dryer South Boston Waterfront
- Rentals with a patio South Boston Waterfront
- Rentals with a fireplace South Boston Waterfront
- Flat rentals South Boston Waterfront
- Pet-friendly rentals South Boston Waterfront
- Rentals with outdoor seating Boston
- Rentals with outdoor seating Suffolk County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- Duxbury Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Onset Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Oakland Beach
- Quincy Market
- Prudential Center