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

Rental unit in Waltham

4.97 out of 5 average rating, 269 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'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)

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 298 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 favorite

Villa in Newton

4.93 out of 5 average rating, 58 reviews

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.

Guest favorite

Rental unit in Brighton

4.9 out of 5 average rating, 40 reviews

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.

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 223 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 favorite

Guest suite in Rockland

4.89 out of 5 average rating, 70 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.

Guest favorite

Rental unit in Downtown Boston

4.8 out of 5 average rating, 10 reviews

Chinatown Condo Public Garden DT Work | Gym & Pool

Welcome to your oasis in the sky! Breathtaking views of Boston skyline and Chinatown 2 bedroom 2 full bathroom luxurious penthouse with balcony! **ASK US ABOUT MONTHLY RATES** The Unit: → Lightning Fast Wi-Fi → Comfortable memory foam mattress beds → Dedicated Workspace → 60” Smart TV → Full Kitchen → Washer & Dryer → View and Lounge → Full Size Gym Ideal for business travelers, medical professionals and corporate clients. ***Ask us about our unbeatable monthly rates!***

Guest favorite

Cottage in Marblehead

4.98 out of 5 average rating, 108 reviews

4 Houses from Harbor | Old Town | Pool | Parking

Marblehead Harbor is just 4 houses away from this beautiful home with a backyard pool in Old Town Marblehead. This quaint antique cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Guest favorite

Condo in East Cambridge

4.98 out of 5 average rating, 50 reviews

Modern New Lux Apt/ King bed close to MIT Harvard

1 Bed/ 1 Bath luxury condo conveniently located in a prime neighborhood in Cambridge, MA. Access to building gym, business center and outdoor gym in summer months. Luxurious KING size bed, 1 full size air mattress 1 couch, Washer/dryer. Convenient walk to cafes & restaurants, Markets, MBTA. Close to Freedom Trail, science museum, Cambridge side mall. NO smoking anywhere in the building. Suitable for children and pets. Street parking only or paid garage across the street.

Superhost

Rental unit in Malden

4.91 out of 5 average rating, 76 reviews

Luxe Serene 1BR 15 min from Boston with Gym & More

You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, pool table, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

Superhost

Home in Revere

4.96 out of 5 average rating, 26 reviews

Boston's Beach Home: Pool, 1min to Beach, Pet +

~Seaside Serenity In Boston~ 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)

Guest favorite

Guesthouse in West Roxbury

4.95 out of 5 average rating, 191 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.