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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Guest favorite

Rental unit in Waltham

4.97 out of 5 average rating, 271 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 298 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Home in Arlington

4.91 out of 5 average rating, 23 reviews

Beautiful Spacious 4BRM House!

Quiet neighborhood. Bring family, friends or co-workers to this great place with lots of room. 4 bedrooms (2 ensuite), 3 full bathrooms plus a half bath Spread over 2 floors: - Floor 1: eat-in kitchen, 1/2 bath, living rm, dining rm, office - Floor 2: 4 bedrooms, 3 bathrooms, bonus room Outside: Yard, Swimming pool (summer months), patio. 2 off-street parking Located right off Route 2 providing quick access to Cambridge/Boston, Alewife T-station (Red line) or Porter and Harvard Square

Guest favorite

Villa in Newton

4.93 out of 5 average rating, 58 reviews

Explore Boston in style! Dream home, pool, sauna.

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - one of the most desirable and safe suburbs of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

Superhost

Rental unit in Brighton

4.86 out of 5 average rating, 35 reviews

Lavish Boston studio with separate bedroom

Experience Boston in a beautiful luxe jr. 1 bedroom unit! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston and tastefully long term. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed ->Game rooms all across the property Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Guest favorite

Home in Norwood

4.96 out of 5 average rating, 26 reviews

the house of id; vintage shop, accessible space

The house of id is a place to stay, shop, and take part. Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

Guest favorite

Home in Weston

4.98 out of 5 average rating, 87 reviews

Spacious vacation unit in premium suburban town

Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2K Sqft of space. There are chickens in the backyard...the host can provide some fresh eggs too if desired.

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 224 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. Winthrop is a welcome relief from the hustle and bustle of the city where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Guest favorite

Guest suite in Rockland

4.89 out of 5 average rating, 70 reviews

Cozy Private Suite halfway between Cape & Boston

Large private room located in the Basement of a single family home. The home is conveniently located less than one minute from route 3 half way between Boston and Cape Code. The room has a full size bed, and a euro lounger that can be used to relax and watch TV or reclyned for sleeping. There is a kitchenette located in the room which has a Fridge with top freezer, a microwave and a Keurig . The private bath is located inside the bedroom. Cool off in the pool during summer months.

Guest favorite

Condo in East Cambridge

4.98 out of 5 average rating, 50 reviews

Modern New Lux Apt/ King bed close to MIT Harvard

1 Bed/ 1 Bath luxury condo conveniently located in a prime neighborhood in Cambridge, MA. Access to building gym, business center and outdoor gym in summer months. Luxurious KING size bed, 1 full size air mattress 1 couch, Washer/dryer. Convenient walk to cafes & restaurants, Markets, MBTA. Close to Freedom Trail, science museum, Cambridge side mall. NO smoking anywhere in the building. Suitable for children and pets. Street parking only or paid garage across the street.

Guest favorite

Rental unit in Holliston

4.96 out of 5 average rating, 119 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favorite

Guest suite in Burlington

4.97 out of 5 average rating, 30 reviews

Stay a While, Studio Apartment-Pet Friendly

Welcome to our fabulous boho chic studio apartment, located 25 minutes North of Boston. We welcome all guests, including your beloved pets! 3/4 of a mile to the nearest MBTA bus stop, 3 miles to Lahey and 6 miles to Winchester Hospital. And best of all, Dunkin Donuts is a 5 minute walk from us ;)