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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Top Guest favourite

Apartment in Waltham

4.97 out of 5 average rating, 344 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)

Top Guest favourite

Apartment in Winthrop

4.97 out of 5 average rating, 325 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.

Top Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 254 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. 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.

Superhost

Apartment in Charlestown

4.89 out of 5 average rating, 73 reviews

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

Superhost

Apartment in Brighton

4.87 out of 5 average rating, 102 reviews

Ideal for long stays | Spacious suite in Boston

Enjoy Boston in an elegant 2 bedroom with sleek interior furnishing 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 -> 24/7 Concierge -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Comfortable Queen Bed -> 1 Twin Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Superhost

Apartment in East Boston

4.83 out of 5 average rating, 180 reviews

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

Guest favourite

Apartment in East Boston

5 out of 5 average rating, 7 reviews

Monthly Skyline Apartment

Welcome to your next retreat, a waterfront haven of fully furnished corporate housing that blends luxury with urban ease. Highlights: • Exceptional location 5-min to the center of downtown • Direct Harborwalk access near Lo Presti Park • Rooftop lounge with skyline vistas, and cozy seating • Pool terrace with grills and herb garden • Chef’s kitchen, billiards, and stylish social spaces • 24/7 fitness center with Peloton and harbor views • Private work rooms and a creative music studio

Top Guest favourite

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 131 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint 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 favourite

Apartment in Revere

4.83 out of 5 average rating, 12 reviews

Boston Designer Beach House | Near Airport

Wake to ocean views, take a morning beach stroll, unwind on the deck, or perfect your swing on the golf simulator—all before sunset cocktails on the rooftop. This 2BR/2BA sanctuary sleeps 6 and blends breezy California vibes with curated vintage style. With a heated pool, firepits, co-working space, free parking, and steps to the train, airport, and beach, it’s your dream escape—just minutes from downtown Boston. The perfect mix of comfort, design, and unbeatable location.

Top Guest favourite

Home in Newton

5 out of 5 average rating, 25 reviews

Villa with private Pool in Boston's Elite Enclave

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, fully stocked kitchen with SS appliances, induction cooktop and double oven, whirlpool tub and bidet toilets, fireplaced 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

Guest favourite

Apartment in Holliston

4.96 out of 5 average rating, 123 reviews

Loch 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

Guest suite in Manchester-by-the-Sea

4.9 out of 5 average rating, 169 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).