Vacation rentals with a pool in Downtown, Boston

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Downtown, Boston

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

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Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 210 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)

Dec 4 – 11

R2,309 ZAR per night

Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 276 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.

Feb 22 – Mar 1

R3,800 ZAR per night

Guest favorite

Villa in Cambridge

4.99 out of 5 average rating, 189 reviews

Phil's Harvard & MIT Home

* An entire apartment with a Harvard bedroom and an MIT bedroom Right at the heart of Harvard University, we are seconds away from university facilities and key attractions, making it a perfect place to stay if you are interested in exploring Harvard. The house is in traditional Victorian style with a lot of history while the interior was renovated in 2016. There are two bedrooms of unique styles: The Harvard and MIT rooms. * Please view my other listings for renting one of the bedrooms only

Oct 24 – 31

R6,144 ZAR per night

Guest favorite

Apartment in Winthrop

4.95 out of 5 average rating, 194 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.

Feb 14 – 21

R5,079 ZAR per night

Guest favorite

Guest suite in Rockland

4.89 out of 5 average rating, 54 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 Code. 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.

Sep 12 – 19

R2,144 ZAR per night

Guest favorite

Apartment in Cambridge

4.92 out of 5 average rating, 13 reviews

Stylish Luxe apartment Cambridge

Enjoy a stylish experience at this centrally-located place. Only 2 miles away from TD Garden, steps away from Lechmere train station. Includes a balcony, a built in desk, and plenty of closet space. You will also get to take advantage of the amazing up to date amenity spaces such as the fitness center, club room, work from home stations, kitchen space, and a roof-deck looking over the beautiful city of Boston & the Charles River. Don’t miss out on this amazing experience!!!

Aug 7 – 14

R5,741 ZAR per night

Guest favorite

Apartment in Boston

4.94 out of 5 average rating, 47 reviews

Ideal for long stays | elegant suite Boston views

Experience Boston in an ultra unique midcentury Jr. 1 bedroom with views of downtown Boston! 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 -> 24/7 Concierge -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

May 10 – 17

R3,446 ZAR per night

Guest favorite

Apartment in Peabody

4.94 out of 5 average rating, 90 reviews

Modern Apartment - Easy Commute to Salem/Boston

This modern, spacious and cozy home was completely renovated at the end of 2022, thoughtfully designed for our family and guests when they visit. It is conveniently located close to popular spots such as Salem, North Shore and Boston (right off route 1 and highway 95). Grocery store, pharmacy, dry cleaners and other amenities are just down the road. In a quiet and friendly neighborhood. We open it up for Airbnb guests seasonally. We look forward to hosting you!

Jul 25 – Aug 1

R2,881 ZAR per night

Guest favorite

Apartment in Revere

4.91 out of 5 average rating, 22 reviews

2 Bedroom apartment

Discover comfort and style in our 2-bed, 2-bath apartment. Modern decor, fully equipped kitchen, and cozy bedrooms await. Enjoy the convenience of nearby attractions, like Revere Beach and downtown Boston. Parking onsite is free. Your home away from home for a memorable Boston experience! The two bedrooms are thoughtfully designed to ensure a restful night's sleep. Both bedrooms are equipped with King sized beds. You will have the apartment all to yourself.

Jan 9 – 16

R2,562 ZAR per night

Superhost

Home in Revere

4.64 out of 5 average rating, 11 reviews

Seaside Serenity Boston -Pet Frndly+Htd Pool

Experience coastal luxury and elegance in this stunning home located right by the tranquil shores of Point of Pines in Revere. This magnificent residence offers the perfect setting for your upcoming getaway, just a one-minute stroll from Revere Beach in Boston. Enjoy exclusive resident-only beach access, allowing you to immerse yourself in the peaceful charm of coastal living. Note : Swimming pool open from (April 30- Sep 30)

Nov 18 – 25

R14,623 ZAR per night

Guest favorite

Apartment in Belmont

4.92 out of 5 average rating, 12 reviews

Luxury 2Bd 2Bth, King Beds, Fast Wi-Fi, Pool, Gym

Welcome to your urban oasis! Spacious, luxurious, and newly renovated. Easy commute to Alewife, Harvard, & MIT. The Unit: → Lightning Fast Wi-Fi → Comfortable King Beds → Dedicated Workspace → 55” Living Room & Bedroom Smart TV's → Fully Stocked Kitchen → Washer & Dryer → Private Parking The Amenities: → Lounge & Pool Table → Full Size Gym → Pool (Seasonal)

Jun 2 – 9

R5,035 ZAR per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 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.

Jul 28 – Aug 4

R3,164 ZAR per night