House vacation rentals in South Boston

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Popular amenities for South Boston house rentals

House rentals with a pool

Top guest favorite
Home in Hull
5 out of 5 average rating, 18 reviews

NEW! Walk To Beach! Sunshine House

TraciRating, 5 stars3 months ago
We had a Great Stay for a Few Days from Texas! The house is super Cute, and Perfect to have Family gathering. Thanks for welcoming us into Your Bnb!
Top guest favorite
Home in Newton
5 out of 5 average rating, 19 reviews

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars3 weeks ago
Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.
Top guest favorite
Home in Lakeside Marblehead
5 out of 5 average rating, 17 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

AlanaRating, 5 stars3 weeks ago
Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!
Top guest favorite
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars2 weeks ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
Top guest favorite
Home in Norwood
4.95 out of 5 average rating, 44 reviews

the house of id; vintage shop, accessible space

JasonRating, 5 stars1 week ago
Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!
Guest favorite
Home in Weston
4.97 out of 5 average rating, 95 reviews

Spacious vacation unit in premium suburban town

LucyRating, 5 stars3 weeks ago
Scott was very easy to communicate with, and he was very nice. They were so thoughtful and even left us a dozen eggs from their backyard chickens! The place was spacious and peaceful. Check in and checkout process was very easy!
Home in Weymouth
4.93 out of 5 average rating, 45 reviews

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

JenniferRating, 5 stars1 week ago
We had a great time staying in Weymouth, (June 2025). Shortly after our arrival, the host came over to welcome us and show us the place, which is accurate to the listing photos. He gave us some local recommendations. (Take the ferry to Boston!) The house was well stocked with kitchen plates/utensils, blankets/towels, etc. We enjoyed the pool/hot tub, playing pool, board games in the dining room, etc. It was a great place for my family to chill out after the busy days in Boston, Salem, etc. The beds were very comfy memory foam style. Lots of places to relax watching boats on the river and amazing sunsets. My family loved the house and we would stay there again.
Superhost
Home in Canton
4.88 out of 5 average rating, 25 reviews

Hidden Gem near Boston w/ Private lake access

RachaelRating, 5 stars1 month ago
Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!

Weekly house rentals

Guest favorite
Home in South Boston
4.96 out of 5 average rating, 54 reviews

Cozy, comfortable and convenient

HeidiRating, 5 stars2 weeks ago
We can’t rave enough about how wonderful of a host Steve was! My friends and I visited Boston for the first time for my birthday and Steve not only was incredibly responsive and made sure we were well taken care of the entire trip, but he also got a surprise Birthday cake to celebrate our special occasion. Steve was also very generous to let us stay longer in the Airbnb when our flight got delayed. He also had a great list of nearby restaurant recommendations and things to do. The Airbnb was fantastic and so clean and in a great location. The beds are comfy, utilities in great shape, and the living room and patio was such a perfect space to hangout. We all agreed that this was hands down the best Airbnb experience that we’ve ever had. Hats off to you Steve. We will definitely be back again for another amazing stay! Such a wonderful, stress free stay.
Guest favorite
Home in Charlestown
4.98 out of 5 average rating, 53 reviews

Spacious & Pet-Friendly Modern Home in Charlestown

KaraRating, 5 stars1 day ago
Wonderful place. We really appreciated the thoughtful touches and attention to detail. Great place and good location for exploring. We used rideshare and the train to get to the sights throughout Boston.
Superhost
Home in South Boston
5 out of 5 average rating, 4 reviews

5BR3B By Subway Downtown

SarahRating, 5 stars1 month ago
Great location!!! We were in town for a graduation, the location is super close to the train station and there are restaurants around the area. The house is conveniently located and is spacious. It was large enough to accommodate our entire party of 7. The rooms are spread between the first and basement floors. It was a great stay, we loved Boston! I would recommend and stay again.
Guest favorite
Home in South Boston
5 out of 5 average rating, 15 reviews

Private Parking! 4BR Family Home in South Boston

DavidRating, 5 stars1 week ago
Alessandra’s place was very nice and exactly what we needed for a group trip. In a good area/close enough to places we wanted to go (Fenway, Seaport, etc.).
Guest favorite
Home in South Boston
4.95 out of 5 average rating, 63 reviews

Beautiful Southie Single Family

ShaanRating, 5 stars1 week ago
Charles was super communicative and the place was as described. We’d be happy to stay again in the future.
Top guest favorite
Home in Watertown
4.95 out of 5 average rating, 111 reviews

Absolutely Gorgeous 3 Bedroom Close to Boston

CarolRating, 5 stars1 week ago
We were very comfortable as a 3 generation family. Thoughtful details and clear instructions were very helpful and appreciated.
Superhost
Home in Dorchester
4.7 out of 5 average rating, 20 reviews

Stylish Condo with Parking/Wi-Fi

AyushRating, 5 stars3 weeks ago
It was a very pleasant stay at your house - it was very clean and very safe. Our parents had the most wonderful time staying there. Irvin was very responsive and always available during the entirety of our stay.
Superhost
Home in Cambridge
4.84 out of 5 average rating, 411 reviews

City Oasis |Yard |Walk To Harvard MIT Train

MaudRating, 5 stars1 week ago
I had an amazing stay at Juan Carlos’s place. He responded immediately and was very helpful whenever I needed anything. The kitchen is brand new and fully equipped with all the utilities you could possibly need. The apartment is located in a quiet, nice neighborhood and everything was spotlessly clean. It’s within walking distance to Harvard Business School and probably also to MIT. There’s also a Whole Foods just a 5-minute walk away. The place was easy to access, very comfortable, and felt safe at all times. Juan Carlos is a super friendly host. I had a late flight and he kindly let me check out an hour later without any problem. I’d definitely recommend this place and would be happy to stay here again!

Private house rentals

Top guest favorite
Home in Greater Mattapan
4.98 out of 5 average rating, 62 reviews

Brand New 4BR 2.5Bath House 20Min Downtown Boston

KellyRating, 5 stars1 day ago
Pamela’s place was very comfortable and well-equipped. We really appreciated the convenience of having two parking spaces. The rooms were cozy, spotless, and thoughtfully arranged. Pamela provided everything we needed for a seamless stay. The apartment is about a 20-minute drive to downtown Boston, making it easy for us to explore top attractions like the Freedom Trail, Harvard, MIT, various museums, and a wide array of great restaurants. Pamela was a very attentive host and always responded promptly to our messages. One of the standout features of our stay was the stress-free check-out process. Unlike some Airbnb hosts who charge a high cleaning fee and still require guests to strip beds, take out the trash, etc., Pamela had no check-out demands—the cleaning crew handled everything. This was a huge relief as we had to catch a flight. Pamela made our stay in Boston truly enjoyable, and we will book her place again the next time we visit Boston.
Guest favorite
Home in Roxbury
4.98 out of 5 average rating, 80 reviews

Boston Home: 5BR, 6 Beds, Sleeps 12, Free Parking!

MelissaRating, 5 stars5 days ago
We had a fantastic multigenerational family stay! The host was exceptionally generous in allowing us to check in early after our red-eye flights, which was a huge help. The home was clean, spacious, and perfect for our group of adults and teens. Thoughtful touches and great communication made the stay smooth and comfortable. Highly recommend!
Guest favorite
Home in Jamaica Plain
4.96 out of 5 average rating, 84 reviews

Beaut private close univ+hospital

KatherineRating, 5 stars2 weeks ago
Maria was very helpful and kind. The airbnb was in a great location - I chose it to be close to a friend’s home. Maria was helpful in recommending an excellent breakfast diner close by. The Airbnb was clean, spacious and lovely. I highly recommend Maria!
Superhost
Home in Jamaica Plain
5 out of 5 average rating, 15 reviews

Brookline Carriage House, Longwood, Fresh Eggs!

WilliamRating, 5 stars3 weeks ago
Beautiful house in a beautiful neighborhood. We loved staying here!
Superhost
Home in Quincy
5 out of 5 average rating, 3 reviews

Studio w seaside deck access

GarlandRating, 5 stars3 months ago
This is my third booking at Kay's place. That should say enough when there are many other choices.
Guest favorite
Home in Winthrop
4.87 out of 5 average rating, 70 reviews

Cozy & Modern Entire Residential Home ❤️

DavidRating, 5 stars2 days ago
We loved the apartment, it was very clean and beautifully decorated. As a family of four we fit comfortably. It’s in a perfect location for getting around Massachusetts. The town was very cute with lots of delicious restaurants and so close to the beach. After a whole day of sightseeing and walking it was nice to come back to the home relax and watch tv in front of the fireplace. Thank you Carmen for the lovely stay.
Top guest favorite
Home in Hull
4.97 out of 5 average rating, 31 reviews

4 bd Ocean View, Dual Deck, Beach Front Retreat

KamilRating, 5 stars1 day ago
We had a blast at this property. The location is perfect and the house was exactly as pictured. The hosts are very flexible and accommodating!
Superhost
Home in Somerville
4.93 out of 5 average rating, 61 reviews

Beautiful appartement - quiet location - downtown

ReginaRating, 5 stars4 weeks ago
Lionel’s place was spotless and was in the perfect location! The easy parking was a huge plus too. Lionel was incredibly accommodating and responsive, and we will absolutely be staying here again next time we go to Boston!

Quick stats about house rentals in South Boston

  • Total rentals

    30 properties

  • Nightly prices starting at

    R1,070 ZAR before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

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