
Vacation 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.

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.

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)

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.

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 • Complimentary 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

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.

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!

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!

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

2BR Penthouse Boston Common DT
***2 Bedroom Penthouse with Balcony in Boston Downtown Chinatown!*** MassLiving offers a wide range of furnished apartment homes in Boston and Cambridge. Breathtaking views of Boston skyline and Back-Bay in your luxurious 2 bedroom 2 full bathroom penthouse with Gym and Roof Top! The Condo: → Lightning Fast Wi-Fi → Lux memory foam mattress beds → Dedicated Workspace → Full Kitchen → Washer & Dryer → Full Size Gym 24/7 FREE → 2 Elevators → 2 Folding beds - Baby Crib and High-chair

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.

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

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...
Popular amenities for South Boston Waterfront rentals with a pool
House rentals with a pool

Luxury Ultra Modern House in Newton ; Boston

Elegant & Spacious~Easy Boston Access! STR-25-22

Pet-friendly 4-Bed Home w/Pool, Nature Trails

Bauhaus Retreat in Nature Preserve

Boston 15 min away.

Waterfront Beauty

Beautiful Spacious 4BRM House!

Large & beautiful home, shared pool and yard
Other vacation rentals with a pool

The Attia

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,

Experience Hotel Concierge Service

Luxury suite with room divider near downtown

Ideal for long stays | Spacious suite in Boston

The Lacks- Perfect for Monthly Stays

Lux 2BR in Assembly Square | Pool & Fitness Center

Bright & Modern @ MIT
Quick stats about vacation rentals with a pool in South Boston Waterfront

Total vacation rentals
Explore 50 vacation rentals in South Boston Waterfront

Nightly prices starting at
South Boston Waterfront vacation rentals start at $166 CAD per night before taxes and fees

Verified guest reviews
Over 170 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of South Boston Waterfront vacation 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
Destinations to explore
- Rentals with a patio South Boston Waterfront
- Rentals with outdoor seating South Boston Waterfront
- Family-friendly rentals South Boston Waterfront
- Pet-friendly rentals South Boston Waterfront
- Fitness-friendly rentals South Boston Waterfront
- Rentals with beach access South Boston Waterfront
- Rentals with a washer and dryer South Boston Waterfront
- Apartment rentals South Boston Waterfront
- Rentals with a fireplace South Boston Waterfront
- Rentals with pools Boston
- Rentals with pools Suffolk County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- MIT Museum
- Good Harbor Beach
- Freedom Trail
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Onset Beach
- Quincy Market
- North Hampton Beach
- Rye North Beach
- Prudential Center
- Oakland Beach
- White Horse Beach




