
Holiday 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.

Stylish 1BR in Assembly Square | Pool, Gym & Views
Experience elevated living at its finest in the heart of Assembly Square, where sophistication, comfort, and style blend seamlessly to create a luxurious urban escape. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complementary gourmet coffee, plush linens and premium bath essentials • 24th-Floor Lookout Lounge offering breathtaking panoramic views of Boston • State-of-the-art fitness center, spin studio, yoga deck & outdoor wellness spaces

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.

Panoramic City-Skyline MIT/Harvard CIC Kendall Sqr
Experience your next high rise apartment retreat in Kendall Square, where sleek interiors harmonize with panoramic city skyline views through large windows. Immerse yourself in a fully equipped kitchen and queen sized bedrooms. Explore the building's shared gym, outdoor garden and business center. Enjoy proximity to innovation hubs such as Harvard Square and Cambridge Innovation Center, creating a vibrant/comfortable retreat. ✔ Shared Gym ✔ City Skyline ✔ Work Station ✔ Sleek Stylish Design

Hidden Gem near Boston w/ Private lake access
Waterfront 3BR home 1 mile from commuter rail to Boston. 1 mile from Blue hills ski. 2.2 miles from New England's 1st and only TopGolf. This 3BR, 2.5 BA features an open floor plan w/ view of your private lake from the kitchen and dining rooms. Head downstairs to play pool, ping pong or darts. Or relax by the fire and watch tv (all streaming channels). Warmer months turns into a resort: Fishing, boating, swimming, grill, fire pit, furnished cabanas, hiking the blue hills and much much more.

Beautiful Spacious 4BRM House!
Quiet neighborhood. Lots of room. Enclosed back yard during summer months (June 21 - September 20) 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, unheated swimming pool (summer 6/21-9/20), patio. 2 off-street parking. Has STAIRS. Off Route 2. Quick access to Cambridge/Boston, Alewife Train station

Beautiful private suite with balcony|fully stocked
Enjoy Boston in an elegant 2 bedroom/1 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” Roku TV Master Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 1 Queen Bed -> 1 Twin Bed -> 1 Full Bed Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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.

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). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...
Popular amenities for Brookline rentals with a pool
House rentals with a pool

Quiet/Private Neighborhood

Lake House in the City

Boston 15 min away.

Waterfront Beauty

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Large & beautiful home, shared pool and yard

Well-Maintained House in a Quiet Neighborhood.

Private & Comfy New England Guest Suite (I95/I93)
Other holiday rentals with a pool

Gallery like studio with room divider near city

The Pasteur-elegant 2BR near downtown

Stylish and Cozy at Revere Beach

Ideal for long stays | Spacious suite in Boston

Lavish Boston studio with separate bedroom

The Fleming-Gym, W/D, studio near City

Lovely Boston studio with bedroom and city views!

Stunning 2BR/2BA APT in Vibrant Assembly Square
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹19,615 | ₹17,546 | ₹16,106 | ₹15,746 | ₹16,646 | ₹16,646 | ₹15,206 | ₹14,397 | ₹15,206 | ₹19,885 | ₹17,906 | ₹17,906 |
| 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 holiday rentals with a pool in Brookline

Total holiday rentals
Explore 100 holiday rentals in Brookline

Nightly prices starting at
Brookline holiday rentals start at ₹4,499 per night before taxes and fees

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

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
100 of Brookline holiday 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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