
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.

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.

Lux 2BR in Assembly Square | Pool & Fitness Center
Welcome to your modern retreat in the heart of Assembly Square, where comfort meets luxury and convenience is just steps away. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • Sky Lounge on the 21st floor with stunning Boston view • 24/7 fitness center, yoga studio, and artist space • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

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

Lovely Boston studio with bedroom and city views!
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.

Elegant & Spacious~Easy Boston Access! STR-25-22
Exclusive retreat in the heart of Boston's premier neighborhood. Minutes away from top Boston's attractions , our space offers the perfect blend of comfort and convenience. Spacious bedrooms, study/ living rm with king bed upon request, fully stocked kitchen with SS appliances, induction cooktop and double oven, whirlpool tub and bidet toilets, library for those family evening over the board games on main floor. Quiet space with massage chair and home theater TV seating on ground floor

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

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

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.
Popular amenities for Brookline rentals with a pool
House rentals with a pool

Bauhaus Retreat in Nature Preserve

Boston 15 min away.

Waterfront Beauty

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Large & beautiful home, shared pool and yard

Spacious 3-BR Furnished Beach Home
Other holiday rentals with a pool

Peaceful suite in Boston with city views

Gallery like studio with room divider near city

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,

Ideal for long stays | Spacious suite in Boston

Cozy Boston studio

The Lister-Luxurious Studio Near Heart of Boston

Central 2BR Boston w/Pool views near Public Garden

Elegant Boston suite
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 188 | € 168 | € 154 | € 151 | € 160 | € 160 | € 146 | € 138 | € 146 | € 191 | € 172 | € 172 |
| 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 € 43 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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