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

Apartment in Waltham

4.97 out of 5 average rating, 292 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 favourite

Apartment in Winthrop

4.96 out of 5 average rating, 301 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

Apartment in Winthrop

4.96 out of 5 average rating, 229 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

Cottage in Westford

4.92 out of 5 average rating, 36 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Guest favourite

Apartment in Ipswich

5 out of 5 average rating, 31 reviews

Dunover Farm. One bedroom apartment.

Welcome to our fully renovated apartment on our charming farm retreat near breathtaking Cranes Beach! 1-Bedroom, 1-bath private apartment Outside, you'll find a spacious patio and pool area where you can soak up the tranquility of the farm. Sip your morning coffee with the sheep, or savor a glass of wine in the evening as you enjoy the view of the horses. We are close to the quaint town of Ipswich, minutes to Cranes Beach, minutes to MBTA commuter rail train, and only 40 minutes to Boston.

Guest favourite

Home in Marblehead

5 out of 5 average rating, 10 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

Enjoy poolside fun & daily nature walks! Spread out in this 4-bedroom, 1.5 bath home near Redd's Pond, nature trails and Old Town Marblehead. Beautiful exposed beams are featured in the large living and dining room area with plenty of space to play games or share some laughs. Three of the four bedrooms are located on the first floor along with one full and one half ensuite bath, making single-floor living possible. The fenced-in pool and patio area are just waiting for you to come and enjoy.

Guest favourite

Guesthouse in Maynard

5 out of 5 average rating, 27 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

Superhost

Apartment in East Boston

4.85 out of 5 average rating, 137 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

Cottage in Marblehead

4.98 out of 5 average rating, 108 reviews

Pool in Old Town Marblehead 4 Houses from Harbor

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

Home in Gloucester

5 out of 5 average rating, 11 reviews

Twin Shores Poolside Haven

Welcome to Twin Shores Poolside Haven, steps from the North Shore’s best beaches! Escape to this charming 3-bedroom, 2-bath home that sleeps 8. Nestled just short walks away from the pristine shores of Good Harbor Beach in Gloucester and Long Beach in Rockport, this vacation rental promises sun-soaked days and tranquil evenings by the pool. Book today and start making unforgettable memories on the beautiful shores of Rockport and Gloucester, MA!

Guest favourite

Apartment in Holliston

4.96 out of 5 average rating, 120 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

Guest suite in Manchester-by-the-Sea

4.92 out of 5 average rating, 149 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).