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.

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Superhost
A modern living area is shown, featuring a white sofa with black and cream accents. Natural light fills the space through large windows adorned with dark curtains. A stylish area rug anchors a coffee table, with a sleek work desk positioned nearby.
Apartment in Chelsea
4.79 out of 5 average rating, 56 reviews

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.

Top Guest favourite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Apartment in Waltham
4.97 out of 5 average rating, 392 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)

Top Guest favourite
The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.
Apartment in Winthrop
4.97 out of 5 average rating, 333 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 favourite
A bright living space is furnished with a light-colored sofa and a wooden coffee table. A large wall-mounted TV is positioned above a light wood sideboard. A round mirror and a floor lamp add to the decor, while a dining area with a wooden table and benches is situated near a window adorned with natural light.
Apartment in Brighton
4.89 out of 5 average rating, 101 reviews

Luxury suite with room divider near downtown

Experience Boston in this incredible eye-catching studio. Comes with a room divider for 1 bedroom like feel! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston tastefully. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Top Guest favourite
A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.
Apartment in Winthrop
4.96 out of 5 average rating, 265 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. 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.

Guest favourite
Apartment in Charlestown
4.91 out of 5 average rating, 138 reviews

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

Guest favourite
A spacious studio apartment is presented, featuring a full bed with soft linens and decorative pillows. Natural light fills the room through large windows, which are dressed with elegant curtains. A modern seating area includes a sleek black sofa and an armchair, creating a comfortable relaxation space.
Apartment in Beachmont
4.85 out of 5 average rating, 221 reviews

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Superhost
Apartment in Boston
5 out of 5 average rating, 3 reviews

Monthly Seaside Luxury

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

Guest favourite
A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.
Guest suite in Rockland
4.87 out of 5 average rating, 103 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 Cod. 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 favourite
Apartment in East Cambridge
4.9 out of 5 average rating, 10 reviews

2bed Condo in Cambridge w/balcony Garage Parking

2BR Apartment w Balcony in the Heart of Cambridge Welcome to your stylish home away from home! This modern 2-bedroom apartment is located in one of Cambridge's most desirable neighborhoods - just steps from the Charles River, MIT and Kendall Square, and easy access to downtown Boston. • Two beautifully furnished bedrooms with plush mattresses and hotel-style bedding • Private balcony • Bright and open layout • Fully equipped kitchen • Rooms with smart TV and high-speed Wi-Fi

Top Guest favourite
Home in Weston
4.97 out of 5 average rating, 108 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). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Top Guest favourite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 206 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

Popular amenities for Brookline rentals with a pool

When is the best time to visit Brookline?

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Avg. price$360 NZD$322 NZD$296 NZD$289 NZD$306 NZD$306 NZD$279 NZD$264 NZD$279 NZD$302 NZD$160 NZD$121 NZD
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Quick stats about holiday rentals with a pool in Brookline

  • Total holiday rentals

    Explore 90 holiday rentals in Brookline

  • Nightly prices starting at

    Brookline holiday rentals start at $83 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Brookline holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Brookline rentals

  • 4.8 Average rating

    Brookline stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Brookline's top spots, include Jamaica Pond, Reservoir Station, and Brookline Village Station

Destinations to explore