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

Total vacation rentals
Explore 70 vacation rentals in Brookline

Nightly prices starting at
Brookline vacation rentals start at $50 per night before taxes and fees

Verified guest reviews
Over 3,390 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Brookline vacation rentals include wi-fi 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 Boston College Station
Top-rated rentals with a pool in Brookline
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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)
FamilyValueHospitality

Private Suite• Pool • Sleeps 4 • Boston • 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
LocationFamilyBackyard

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.
LocationFamilyGrill

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.
FamilyValueAir conditioning

Spacious quiet Newton Villa *Easy Boston Access!
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, living room 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. STR-25-22
FamilyLocationNearby

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.
FamilyLocationWifi

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.
LocationFamilyPool

The Murthy : Bright • Spotless • W/D
Enjoy Boston in this elegant suite 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 -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!
LocationValueWalkability

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. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.
ValueLocationCleanliness

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.
LocationFamilyComfort

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...
ValueLocationOutdoor spaces

“Luxury 2BR Cambridge | Pool + Parking”
Two blocks from Lechmere Station, with the Green Line running direct to Kendall Square, MIT, and Harvard, this residential 2BR/2BA operates on a different standard than corporate hotel rooms. On-site garage parking runs the elevator straight to your floor, unlimited in-and-out, versus $50-65/night at nearby garages that re-bill on every return. Two full bathrooms, in-unit laundry, a fully equipped kitchen, and shared pool access. Sleeps 5.
FamilyLocationSleep quality
Popular amenities for Brookline rentals with a pool
House rentals with a pool

Luxury lake retreat- pool, fire pit, trails
ValueFamilySleep quality

Beautiful Spacious 4BRM House!
LocationValueCheckout

Private/Quiet Single Family Home
ValueFamilyAmenities

Theatre | Arcade | Pool w. Free 3 Car Parking
LocationFamilyComfort

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
ValueLocationAccess

Boston 15 min away.
FamilyValueTV
Other vacation rentals with a pool

Cozy Urban Stay 1BR | Assembly Row | Gym & Pool
LocationCleanlinessWalkability

Cozy 1BR Near Boston w/ Pool & Gym
FamilyLocationLaundry

Luxury 2b2b downtown Boston
LocationNearbyIndoor spaces

Sunny Quiet 2 BR MIT Hrvrd BU Fenway Longwood
ValueLocationGetting around

Luxury Apartment w King Bed, Shared Pool & Rooftop
ValueLocationView

Luxury 2BR 2BA Condo Fenway Boston Washer&Dryer in
FamilyLocationPool

1 BDRM Retreat | King Bed, Pool, Gym, Parking+ Bus
FamilyLocationPets

Central 2BR Condo in Assembly with Pool, Row Gym,
LocationAccessPool
When is the best time to visit Brookline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $63 | $63 | $85 | $134 | $172 | $166 | $169 | $160 | $169 | $183 | $97 | $73 |
| Avg. temp | 30°F | 32°F | 38°F | 49°F | 58°F | 68°F | 74°F | 73°F | 66°F | 55°F | 45°F | 36°F |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Portland Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Newport Vacation rentals
- Atlantic City Vacation rentals
- Providence Vacation rentals
- Bar Harbor Vacation rentals
- Salem Vacation rentals
- House rentals Brookline
- Townhouse rentals Brookline
- Condo rentals Brookline
- Bed and breakfasts Brookline
- Hotel rooms Brookline
- Rentals with breakfast Brookline
- Rentals with a hot tub Brookline
- Rentals with lake access Brookline
- Apartment rentals Brookline
- Family-friendly rentals Brookline
- Private suite rentals Brookline
- Loft rentals Brookline
- Pet-friendly rentals Brookline
- Rentals with pools Norfolk County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- Boston College
- Northeastern University
- Duxbury Beach
- MIT Museum
- North Hampton Beach
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Things to do Brookline
- Things to do Norfolk County
- Sports activities Norfolk County
- Food tours Norfolk County
- Food and drink Norfolk County
- Landmarks Norfolk County
- Nature and outdoors Norfolk County
- Art and culture Norfolk County
- Cultural tours Norfolk County
- Tours Norfolk County
- Sightseeing Norfolk County
- Things to do Massachusetts
- Cultural tours Massachusetts
- Art and culture Massachusetts
- Art workshops Massachusetts
- Sightseeing Massachusetts
- Outdoors Massachusetts
- Food and drink Massachusetts
- Food tours Massachusetts
- Landmarks Massachusetts
- Water sports Massachusetts
- Tastings Massachusetts
- Wildlife Massachusetts
- Tours Massachusetts
- Nature and outdoors Massachusetts
- Sports activities Massachusetts
- Things to do United States
- Dining United States
- Tours United States
- Museums United States
- Shopping and fashion United States
- Food and drink United States
- Sightseeing United States
- Cultural tours United States
- Entertainment United States
- Workouts United States
- Art and culture United States
- Flying United States
- Art workshops United States
- Sports activities United States
- Architecture United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Nature and outdoors United States
- Beauty United States
- Outdoors United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes







