
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.

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.

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.

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

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.

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!

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.

Condo in Kendall Square MIT/Harvard
Stunning apartment in Kendall Square with all amenities: gym, pool, social room, business center, grills, courtyard. Just a 5-minute walk to MIT, the subway, the Charles River, and a short walk to Beacon Hill and other Boston highlights. Experience vibrant executive and family life with nearby restaurants and cafes. This luxurious, safe complex offers a quiet apartment with high-speed WiFi, HVAC, a sofa bed, a cozy living area, and an open kitchen. Perfect for business or leisure.

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 we may have chickens(hens) in the backyard...

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,
Discover comfort and style in our 2-bed, 2-bath apartment. Modern decor, fully equipped kitchen, and cozy bedrooms await. Enjoy the convenience of nearby attractions, like Revere Beach and downtown Boston. Parking onsite is free. Your home away from home for a memorable Boston experience! The two bedrooms are thoughtfully designed to ensure a restful night's sleep. Both bedrooms are equipped with King sized beds. You will have the apartment all to yourself.

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
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!

the house of id; vintage shop, accessible space
Other holiday rentals with a pool

Peaceful suite in Boston with city views

Sun-filled Unit, Elevator, Pool, Boston College

Ideal for long stays | Spacious suite in Boston

Stylish and Cozy at Revere Beach

Private & Comfy New England Guest Suite (I95/I93)

The Lister-Luxurious Studio Near Heart of Boston

Bright & Modern @ MIT

Central 2BR Boston w/Pool views near Public Garden
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 $214 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
50 of South Boston Waterfront holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Pet-friendly rentals South Boston Waterfront
- Rentals with a washing machine and dryer South Boston Waterfront
- Apartment rentals South Boston Waterfront
- Rentals with a fireplace South Boston Waterfront
- Rentals with beach access South Boston Waterfront
- Fitness-friendly rentals South Boston Waterfront
- Family-friendly rentals South Boston Waterfront
- Rentals with outdoor seating 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
- Duxbury Beach
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Onset Beach
- Quincy Market
- Rye North Beach
- North Hampton Beach
- Oakland Beach
- Prudential Center
- White Horse Beach




