
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.

Boston Modern Apt: Luxe Stay w/ Gym, Parking
Discover Boston from a contemporary luxury apartment with exceptional ambiance and amenities. STRICT NONSMOKING!!! The Unit: → Lightning Fast Wi-Fi → Comfortable King Bed → Dedicated Corporate Office Workspace → 65" Living Room Smart TV → 55" Bedroom Smart TV → Fully Stocked Kitchen → Washer & Dryer → Private Parking The Amenities: → Business Lounge → Pool → Full Size Gym → Gameroom Ideal for business travelers, travel nurses and corporate clients looking to experience Boston in style.

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)

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.

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. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. 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.

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.

Peaceful suite in Boston with city views
Enjoy Boston in an elegant 2 bedroom/bath with sleek interior furnishing for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Beautiful Spacious 4BRM House!
Quiet neighborhood. Lots of room. Enclosed back yard during summer months (June 20 - September 19) 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 - Has STAIRS to bedrooms. Outside: Yard, Swimming pool (summer months), patio. 2 off-street parking. Has STAIRS to outside. Off Route 2. Quick access to Cambridge/Boston, Alewife Train station

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.

Monthly Skyline Apartment
Welcome to your next retreat, a waterfront haven of fully furnished corporate housing that blends luxury with urban ease. Highlights: • Exceptional location 5-min to the center of downtown • Direct Harborwalk access near Lo Presti Park • Rooftop lounge with skyline vistas, and cozy seating • Pool terrace with grills and herb garden • Chef’s kitchen, billiards, and stylish social spaces • 24/7 fitness center with Peloton and harbor views • Private work rooms and a creative music studio

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 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.

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,
Discover comfort and style in our 2-bed, 2-bath apartment. Modern decor, fully equipped kitchen, and cozy bedrooms await. Enjoy the convenience of nearby attractions, like Revere Beach and downtown Boston. Parking onsite is free. Your home away from home for a memorable Boston experience! The two bedrooms are thoughtfully designed to ensure a restful night's sleep. Both bedrooms are equipped with King sized beds. You will have the apartment all to yourself.

Brand New Luxury Retreat w/ Pool & Fitness Center
Experience modern South Boston living in this bright 2BR/2BA apartment! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit washer/dryer, and spacious living areas with oversized windows. Relax by the heated pool, work out in the 24/7 fitness center, or unwind in the lush courtyard with grilling stations. Just minutes from Carson Beach, Downtown Boston, and the Red Line.
Popular amenities for Brookline rentals with a pool
House rentals with a pool

NEW! Walk To Beach! Sunshine House

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Bauhaus Retreat in Nature Preserve

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Ocean Side, Amazing View, close to town/beach, Spa

Hidden Gem near Boston w/ Private lake access

Quiet/Private Neighborhood
Other vacation rentals with a pool

The Attia

3 King Beds 1 Bath Apt w/ Pool

Ideal for long stays | Chic downtown glass suite

Stylish and Cozy at Revere Beach

Ideal for long stays | Spacious suite in Boston

Lavish Boston studio with separate bedroom

The Harvey: Large • Near T • Gym • Kitchen • W/D

The Salk-Beautiful Boston Studio
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $305 CAD | $273 CAD | $250 CAD | $245 CAD | $259 CAD | $259 CAD | $316 CAD | $339 CAD | $297 CAD | $339 CAD | $278 CAD | $278 CAD |
| Avg. temp | -1 °C | 0 °C | 4 °C | 9 °C | 15 °C | 20 °C | 23 °C | 23 °C | 19 °C | 13 °C | 7 °C | 2 °C |
Quick stats about vacation rentals with a pool in Brookline

Total vacation rentals
Explore 100 vacation rentals in Brookline

Nightly prices starting at
Brookline vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 2,300 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
100 of Brookline vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Brookline rentals

4.7 Average rating
Brookline stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Brookline’s top spots, include Jamaica Pond, Reservoir Station, and Brookline Village Station
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