
Holiday rentals with a pool in Brookline
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Brookline

Total holiday rentals
Explore 80 holiday rentals in Brookline

Nightly prices starting at
Brookline holiday rentals start at $64Â SGD per night before taxes and fees

Verified guest reviews
Over 2,870 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 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
Top-rated rentals with a pool in Brookline
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Explore Boston in style! Dream home (STR-26-3)
Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, office with bed, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - desirable and safe suburb 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.

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)

The Watkins : Elevated Cozy • W/D • Amenities
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 Air bed and single rolling cot are only available on request! Ideal for business travelers, couples, nurses, those in hospital treatment and

World Cup Boston • Pool • Sleeps 4 • Near Airport
Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

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.

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 ✔ Patio

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.

Summer heated Pool ~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

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.

Beautiful Spacious 4BRM House!
A thoughtfully cared-for New England home best suited for a quiet, comfortable stay in a residential neighborhood. Enclosed back yard with pool during summer (June 21 - September 20) 4 bedrooms (2 ensuite), 3 full bathrooms, 1 half bath. Spread over 2 floors: - Floor 1: eat-in kitchen, 1/2 bath, living, dining, 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.

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

NEW! Walk To Beach! Sunshine House

Bauhaus Retreat in Nature Preserve w/ Pool

Amazing Home Minutes from Gillette

Boston 15 min away.

Free Parking Close to All Major Boston Attractions

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Spacious 3-BR Furnished Beach Home

Hidden Gem near Boston w/ Private lake access
Other holiday rentals with a pool

Brand New Luxury Retreat w/ Pool & Fitness Center

Hotel-like amenities, all the comforts of home!

2b2b luxury apartment downtown Boston

The Franklin: Wellness • Aesthetic • W/D • Gym

Stylish StudioLux in Vibrant East Boston

Spacious 1BR in Upscale Kendall Square Apt Complex

World Cup and Gillette Hub: Modern Loft w/ Pool

Modern Lux Seaport Convention center, 2BR 2BA APT
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $81 SGD | $81 SGD | $109 SGD | $224 SGD | $236 SGD | $236 SGD | $216 SGD | $204 SGD | $216 SGD | $234 SGD | $124 SGD | $93 SGD |
| 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 |
Destinations to explore
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- Rentals with a patio Brookline
- Pet-friendly rentals Brookline
- Rentals with breakfast Brookline
- Apartment rentals Brookline
- Rentals with a fireplace Brookline
- House rentals Brookline
- Townhouse rentals Brookline
- Rentals with a hot tub Brookline
- Rentals with an EV charger Brookline
- Bed and breakfasts Brookline
- Rentals with outdoor seating Brookline
- Rentals with a washing machine and dryer Brookline
- Flat rentals Brookline
- Loft rentals Brookline
- Fitness-friendly rentals Brookline
- Rentals with a firepit Brookline
- Hotel rooms Brookline
- Family-friendly rentals Brookline
- Private suite rentals Brookline
- Rentals with lake access Brookline
- Rentals with pools Norfolk County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Northeastern University
- Gillette Stadium
- Freedom Trail
- Boston Convention and Exhibition Center
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Onset Beach
- Quincy Market
- Roxbury Crossing Station
- North Hampton Beach
- Museum of Fine Arts
- Boston College
- Things to do Brookline
- Things to do Norfolk County
- Tours Norfolk County
- Sightseeing Norfolk County
- Sports activities Norfolk County
- Art and culture Norfolk County
- Food and drink Norfolk County
- Things to do Massachusetts
- Food and drink Massachusetts
- Sports activities Massachusetts
- Sightseeing Massachusetts
- Art and culture Massachusetts
- Nature and outdoors Massachusetts
- Things to do United States
- Sightseeing United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Food and drink United States
- Sports activities United States
- Nature and outdoors United States
- Wellness United States







