
Vacation rentals with a pool in Brookline
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Brookline
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Brookline rentals with a pool
House rentals with a pool

Home in West Roxbury
4.71 out of 5 average rating, 7 reviewsLuxury Ultra Modern House in Newton ; Boston
Ryan MRating, 5 stars39 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, 13 reviewsVilla with private Pool in Boston's Elite Enclave
Fay And JoeRating, 5 stars7 months ago
We had a great family vacation in Serge's beautiful house. A quiet, peaceful neighborhood, everything looked exactly like in the pictures. Everything was clean, Serge's instructions were spot on, and his helpful attitude was unmatched by any Airbnb host I've dealt with in the past. Always proactive, reaching out to make sure we didn't need anything else. Any request was immediately responded to and addressed. We hope to return here in the future, it was really great!

Home in Revere
4.8 out of 5 average rating, 54 reviewsBoston 15 min away.
MelissaRating, 5 stars8 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, 27 reviewsBeautiful Spacious 4BRM House!
DeenaRating, 5 stars4 days ago
We have been using short-term rentals as a family since 2011. This is by far the best appointed house we've ever stayed in. Plenty of everything -- basic groceries, towels, dishes, parking, beds and baths. It's a classic New England home with thoughtful updates. Love the vintage touches! Everything was first rate and we were comfortable for our short visit. We will be back!
Top guest favourite

Home in Norwood
4.97 out of 5 average rating, 34 reviewsthe house of id; vintage shop, accessible space
PrashaRating, 5 stars4 days ago
This place is a VIBE!!! And I am so happy that this place was the exact vibe I was looking for to record my in person podcast. My guests were blown away, my social media was on fire and I am sure my content will be too once it's ready. Thanks Dara & Paige for opening your home so I can bring my dream project to life.
Top guest favourite

Home in Weston
4.98 out of 5 average rating, 90 reviewsSpacious vacation unit in premium suburban town
Mary AnneRating, 5 stars2 months ago
Scott’s apartment is fantastic! It is located on the lower floor of his house. It is very open and light. The bedrooms are spacious and the mattresses extremely comfortable. The kitchen and living area is also spacious, with beautiful views of the woods. There is everything you need for a comfortable stay. The bathrooms are also very well equipped, with very nice towels. There is a washer and dryer, as well as an ironing board and iron. The heating system worked superbly during our stay. We were in the area to visit with family and friends, and the house is located in a perfect location, whether you need drive north or south, east or west! We look forward to staying at Scott's house in the future. Comunication with Scott was very easy and he checked in to see how we were doing. Thank you, Scott, for a lovely stay! We will be back.

Home in Weymouth
4.93 out of 5 average rating, 41 reviewsWeymouth Waterfront Getaway w/ Hot Tub & Pool!
MarissaRating, 5 stars2 weeks ago
This property was awesome!! We so appreciated the gas grill and heater on the porch. Rob walked us through everything and was super friendly. The house was outstanding. Beautiful views. Plenty of rooms, plenty of beds, plenty of space! We loved using the porch and the swimming pool/hot tub!! We would absolutely return!! Thank you for having us!
Guest favourite

Home in Hull
4.96 out of 5 average rating, 23 reviewsSpacious 3-BR Furnished Beach Home
BriannaRating, 5 stars9 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!
Quick stats about vacation rentals with a pool in Brookline
Total rentals
70 properties
Nightly prices starting at
$57 CAD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- North Hampton Beach
- Harvard University
- Brown University
- Onset Beach
- Sagamore Beach
- New England Aquarium
- Faneuil Hall Marketplace
- Scusset Beach
- Goddard Memorial State Park
- Prudential Center
- Symphony Hall
- Isabella Stewart Gardner Museum
- Oakland Beach
- Phillips Beach
- Museum of Fine Arts, Boston
- Pinehills Golf Club
- Hampton Beach State Park
- Roger Williams Park Zoo
- Sandy Point Beach
- Cranston Country Club