Vacation rentals with a pool in Downtown, Boston

Find and book unique homes with a pool on Airbnb

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Popular amenities for Downtown, 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 Hull
5 out of 5 average rating, 17 reviews

NEW! Walk To Beach! Sunshine House

LouiseRating, 5 stars1 month ago
Probably the most enchanting and creative place I’ve ever stayed! Bright, clean and colorful! Brenna and Kyle were friendly, helpful and responsive. Would definitely stay there again.
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 stars4 days 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, 29 reviews

Beautiful Spacious 4BRM House!

SusanRating, 5 stars3 days ago
Maxine anticipated every possible need and so much more available. She went beyond any host I have ever stayed with and I travel quite often. I highly recommend Maxine's place
Top guest favourite
Home in Norwood
4.97 out of 5 average rating, 36 reviews

the house of id; vintage shop, accessible space

NatalieRating, 5 stars2 weeks ago
This has to be the neatest little place on Airbnb in the Boston area, and that's something to be said. Paige and Dara described the place and the experience perfectly, were a dream to communicate with, and were overall humorous hosts. Their in-house shop was very entertaining for us. We will absolutely be staying here again in the future.
Top guest favourite
Home in Weston
4.98 out of 5 average rating, 91 reviews

Spacious vacation unit in premium suburban town

RanuRating, 5 stars4 weeks ago
Thank you Scott for hosting us! The location was perfect for our son’s therapy intensive, and it was peaceful, calm, and a bonus that it was right near the park. Projector worked well, comfortable desk upstairs for working, strong internet, and a great layout for a family. Our kids really enjoyed the books, and we loved the open layout, as well as the backyard space. We also appreciated the fresh eggs — thank you!
Home in Weymouth
4.93 out of 5 average rating, 42 reviews

Weymouth Waterfront Getaway w/ Hot Tub & Pool!

JessicaRating, 5 stars1 week ago
We had a great time staying here. It was raining our entire stay but the closed in porch area allowed us to still feel like we were on vacation and enjoy the view of the harbor.

Quick stats about vacation rentals with a pool in Downtown, Boston

  • Total rentals

    50 properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    710 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Downtown
  7. Rentals with pools