Holiday rentals with a pool in South Boston

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for South Boston rentals with a pool

House rentals with a pool

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars40 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Top guest favourite
Home in Newton
5 out of 5 average rating, 14 reviews

Villa with private Pool in Boston's Elite Enclave

LucyRating, 5 stars2 weeks ago
Serge was helpful with marathon weekend details and was very responsive. House is as described, quite spacious and easily sleeps 8 adults. The game room includes billiards, darts, a massage chair, and 3 comfortable theater chairs. The kitchen is fully equipped with everything needed to prepare large family meals. It’s a 30 minute walk to the Newton Center green line train stop, which is recommended for transportation to and from downtown Boston. The price was a little high, but everything in the area was increased for marathon weekend. Would recommend.
Home in Revere
4.8 out of 5 average rating, 54 reviews

Boston 15 min away.

MelissaRating, 5 stars9 months ago
This is the third year we were able to rent Ediangela’s house. As always it’s beautiful and clean. The pool is spotless. Plenty of space for big groups and absolutely perfect for families with kids of all ages. There’s so much to do on the property itself. She is so kind and responsive. It’s always been amazing every time we stay. It’s becoming our summer staple to come and stay by the pool for a few days of vacation. 10/10 absolutely worth renting this space. This year we brought two 10 year olds, a 5 year old, and a 2 year old, with 4 adults. They had the best time in the little play houses and pool. The adults had a great time as well. If you’re looking for a low key - big fun spot where you don’t have to run around to entertain, this is perfect! Everything you need or may need is on site or minutes away if you need to shop. Including the actual beach. I sincerely hope we get the chance to make it year 4 next summer!
Guest favourite
Home in Arlington
4.93 out of 5 average rating, 30 reviews

Beautiful Spacious 4BRM House!

KarenRating, 5 stars1 week ago
We enjoyed our stay at Maxine’s place. We had 7 people and this home was spacious and clean. Maxine was also very responsive and helpful. I had forgot my jacket here after checkout and was able to arrange to pick it up. The area was also nice and peaceful.
Top guest favourite
Home in Norwood
4.97 out of 5 average rating, 37 reviews

the house of id; vintage shop, accessible space

LeeAnnRating, 5 stars2 days ago
UNBRIDLED JOY. Dara and Paige's house is welcoming right away, with a comfortable open living, dining, and kitchen area filled with fun, bright decor. The house radiates joy and fun and comfort. My friend and I took a last-minute getaway here, and it was exactly what we needed. The colors are both cheerful and calm, and the place is furnished for relaxing cozily. We had a blast shopping the items in the house, which is a wonderful unique twist. Everything was exactly as described and better. Communication was SUPERB. You couldn't ask for two kinder or more caring hosts. We especially appreciated the attention to accessibility since I have some mobility issues. We can't wait to go back again. Everything about this house raises our spirits and makes us laugh out loud with delight. We loved every moment and are already looking forward to our next stay. THANK YOU!!!!!
Top guest favourite
Home in Weston
4.98 out of 5 average rating, 92 reviews

Spacious vacation unit in premium suburban town

JenniferRating, 5 stars1 week ago
I had a wonderful stay at this Airbnb in Weston, MA. The house was spacious, spotless, and located in a peaceful, wooded neighborhood right next to Cat Rock Park—perfect for relaxing or enjoying nature. It was incredibly quiet, which made for a restful stay. Parking was convenient, and check-in was seamless. Everything about the experience was easy and comfortable. I would absolutely recommend this place to anyone looking for a clean, quiet, and well-located home away from home.
Guest favourite
Home in Hull
4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

BriannaRating, 5 stars10 months ago
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!
Superhost
Home in Canton
4.87 out of 5 average rating, 23 reviews

Hidden Gem near Boston w/ Private lake access

ShannonRating, 5 stars6 months ago
The property was stunning and impeccably clean, matching the description perfectly. We had a wonderful time and enjoyed the convenient location with a trail to see horses and access to the lake. The host was incredibly accommodating, and we are looking forward to returning with our family. One suggestion for improvement would be to provide garage access to the house for elderly guests who may have difficulty with stairs, as the pathway, although beautiful, was quite lengthy for my elderly parents. Nonetheless, we all had a fantastic time. Thank you.

Quick stats about holiday rentals with a pool in South Boston

  • Total rentals

    20 properties

  • Nightly prices starting at

    £150 before taxes and fees

  • Total number of reviews

    80 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore