Holiday rentals with a pool in South Boston Waterfront

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Boston Waterfront

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

%{current} / %{total}1 / 1
Superhost
A modern living area is shown, featuring a white sofa with black and cream accents. Natural light fills the space through large windows adorned with dark curtains. A stylish area rug anchors a coffee table, with a sleek work desk positioned nearby.
Flat in Chelsea
4.78 out of 5 average rating, 54 reviews

Boston Modern Apt: Luxe Stay w/ Gym, Parking

Discover Boston from a contemporary luxury apartment with exceptional ambiance and amenities. STRICT NONSMOKING!!! The Unit: → Lightning Fast Wi-Fi → Comfortable King Bed → Dedicated Corporate Office Workspace → 65" Living Room Smart TV → 55" Bedroom Smart TV → Fully Stocked Kitchen → Washer & Dryer → Private Parking The Amenities: → Business Lounge → Pool → Full Size Gym → Gameroom Ideal for business travelers, travel nurses and corporate clients looking to experience Boston in style.

Top guest favourite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Flat in Waltham
4.97 out of 5 average rating, 378 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
The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.
Flat in Winthrop
4.97 out of 5 average rating, 333 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.

Superhost
Flat in Somerville
5 out of 5 average rating, 4 reviews

Stylish 1BR in Assembly Square | Pool, Gym & Views

Experience elevated living at its finest in the heart of Assembly Square, where sophistication, comfort, and style blend seamlessly to create a luxurious urban escape. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complementary gourmet coffee, plush linens and premium bath essentials • 24th-Floor Lookout Lounge offering breathtaking panoramic views of Boston • State-of-the-art fitness center, spin studio, yoga deck & outdoor wellness spaces

Top guest favourite
A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.
Flat in Winthrop
4.96 out of 5 average rating, 265 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
The living area features a sleek design, with large windows offering panoramic city skyline views. A comfortably upholstered sofa is accompanied by stylish seating and a decorative table. A flat-screen HDTV stands against the wall, while greenery adds a touch of nature to the modern space.
Flat in Kendall Square
4.83 out of 5 average rating, 6 reviews

Panoramic City-Skyline MIT/Harvard CIC Kendall Sqr

Experience your next high rise apartment retreat in Kendall Square, where sleek interiors harmonize with panoramic city skyline views through large windows. Immerse yourself in a fully equipped kitchen and queen sized bedrooms. Explore the building's shared gym, outdoor garden and business center. Enjoy proximity to innovation hubs such as Harvard Square and Cambridge Innovation Center, creating a vibrant/comfortable retreat. ✔ Shared Gym ✔ City Skyline ✔ Work Station ✔ Sleek Stylish Design

Guest favourite
A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.
Flat in Brighton
4.96 out of 5 average rating, 115 reviews

Peaceful suite in Boston with city views

Enjoy Boston in an elegant 2 bedroom/bath 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 -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Top guest favourite
Guest suite in Lakeside Marblehead
5 out of 5 average rating, 32 reviews

Headers’ Haven

Your family will be close to everything when you stay at this centrally-located in-law suite. Walking distance to beaches, shops, and restaurants. Steps from Steer Swamp Conservation Area. 13 miles from Boston, and an easy 10 min drive to Salem. Cool off in the pool during the summer heat, or relax in the hot tub on a chilly evening. There’s room for everyone on the pull out sectional to snuggle up for a movie night, complete with popcorn and candy machines. Sure to be a fun and cozy stay!

Guest favourite
A spacious studio apartment is presented, featuring a full bed with soft linens and decorative pillows. Natural light fills the room through large windows, which are dressed with elegant curtains. A modern seating area includes a sleek black sofa and an armchair, creating a comfortable relaxation space.
Flat in Beachmont
4.85 out of 5 average rating, 208 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
A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.
Guest suite in Rockland
4.88 out of 5 average rating, 101 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 Cod. 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.

Top guest favourite
Home in Weston
4.97 out of 5 average rating, 107 reviews

Spacious vacation unit in premium suburban town

Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Top guest favourite
The inviting backyard features a clear pool reflecting a serene atmosphere. A patio with seating is visible near the pool. The house, with large windows, provides a bright indoor space that overlooks the outdoor area, surrounded by lush greenery and charming landscaping.
Cottage in Lakeside Marblehead
4.99 out of 5 average rating, 144 reviews

Antique Home - Steps from Harbor - Private Pool

Just steps from Marblehead Harbor, this antique home offers a private backyard pool and beautiful garden. Walk to The Barnacle (300 ft), Fort Sewall, Gas House Beach, and Old Town Marblehead — easy and walkable access to all. Features one king bed, two twins, and a queen sofa bed. Enjoy walkable dining and shopping plus two tandem off-street parking spots—your perfect coastal getaway with plenty of amenities nearby.

Popular amenities for South Boston Waterfront rentals with a pool

Quick stats about holiday rentals with a pool in South Boston Waterfront

  • Total holiday rentals

    Explore 50 holiday rentals in South Boston Waterfront

  • Nightly prices starting at

    South Boston Waterfront holiday rentals start at € 102 per night before taxes and fees

  • Verified guest reviews

    Over 170 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    50 of South Boston Waterfront holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across South Boston Waterfront rentals

  • 4.8 Average rating

    South Boston Waterfront stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    South Boston Waterfront’s top spots include Boston Children's Museum, Broadway Station and South Station Tower