Holiday rentals with a pool in Boston

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Boston

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit in Waltham

4.97 out of 5 average rating, 252 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 will love this large 400 sq. ft private 1 bedroom studio. This unit has a private 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)

Guest favourite

Rental unit in Winthrop

4.97 out of 5 average rating, 289 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

Rental unit in Brighton

5 out of 5 average rating, 16 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.

Guest favourite

Loft in Brockton

4.97 out of 5 average rating, 38 reviews

Modern Studio Apt with Pool

This warm and inviting, spacious basement apartment is located in the Historical west side of Brockton, prime location for all the “Hotspots” of Mass. Minutes to route 24 and 15 minutes walk or you can take the bus in front of the house to commuter rail to Boston. Perfect for long term stays! or just a few nice days of tranquility. Your home-away-from-home awaits you! You have access to heated saltwater pool and beautiful garden. Expect a quiet and relaxing environment while staying with us!

Guest favourite

Rental unit in Winthrop

4.95 out of 5 average rating, 216 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. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. 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

Home in Hopkinton

4.94 out of 5 average rating, 143 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed. My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families.

Guest favourite

Rental unit in Holliston

4.96 out of 5 average rating, 118 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favourite

Home in North Andover

4.95 out of 5 average rating, 147 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Guest favourite

Cottage in Marblehead

4.98 out of 5 average rating, 103 reviews

4 Houses from Harbor | Old Town | Pool | Parking

Quaint antique cottage with a pool that is located 4 houses from the harbor in Marblehead's Historic District — steps The Barnacle Restaurant. Private backyard pool with indoor and outdoor seating. Close to attractions like Fort Sewall, Fort Beach, and local eateries. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Guest favourite

Condo in Acton

5 out of 5 average rating, 5 reviews

Updated cozy one bedroom

Clean and comfortable one bedroom apartments. Recently renovated with stylish furnishings, and decor. Fully furnished with all kitchenware, and linens. Cable TV, heat, hot water, and wifi are included. Easy access to many shops, restaurants, and grocery. Card-Op laundry on the building. Safe, and secure location. 10% discount for 30 nights, or longer.

Guest favourite

Guest suite in Manchester-by-the-Sea

4.91 out of 5 average rating, 140 reviews

Modern Space With Pool Close To Singing Beach

Situated in a very quiet neighborhood, you will rest comfortably. Drive five minutes and you can be in downtown Manchester-By-The-Sea with singing beach and great restaurants. secluded back yard with fire pit and pool. Inside you'll find a freshly updated and modern living space with fireplace. (Pool open from 5/27-9/8).

Guest favourite

Guesthouse in West Roxbury

4.95 out of 5 average rating, 187 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.