
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.

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. ā Shared Gym ā City Skyline ā Work Station ā Sleek Stylish Design

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.

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 -> 65ā 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.

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.

2bed Condo in Cambridge w/balcony Garage Parking
2BR Apartment w Balcony in the Heart of Cambridge Welcome to your stylish home away from home! This modern 2-bedroom apartment is located in one of Cambridge's most desirable neighborhoods - just steps from the Charles River, MIT and Kendall Square, and easy access to downtown Boston. ⢠Two beautifully furnished bedrooms with plush mattresses and hotel-style bedding ⢠Private balcony ⢠Bright and open layout ⢠Fully equipped kitchen ⢠Rooms with smart TV and high-speed Wi-Fi

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...

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.

Serenity - 36ā Aft Cabin Carver
At Constitution Marina's Bed & Breakfast Afloat you can enjoy the ambiance, the comfort, the romance of staying ON THE WATER with all the amenities of a modern hotel, at rates as low as you'll find anywhere in Boston! For boats with 2 staterooms, there is an additional fee of $100.00 plus tax/night if the 2nd room is rented. The 2nd room is booked directly through the host.

Antique Home - Steps from Harbor - Private Pool
HIGHLIGHTS: ⢠Marblehead Harbor - 4 houses away ⢠Private backyard pool ⢠0.2 Miles to Fort Sewall ⢠0.3 Miles to Gas House beach ⢠0.4 Miles to Old Town Marblehead ⢠300 Feet to The Barnacle Restaurant ⢠Walkable to restaurants and shopping ⢠Beautiful private garden ⢠One king bed ⢠Two twin beds ⢠One queen sofa bed ⢠2-car off-street tandem parking spaces
Popular amenities for South Boston Waterfront rentals with a pool
House rentals with a pool

NEW! Walk To Beach! Sunshine House

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

Bauhaus Retreat in Nature Preserve w/ Pool

Boston 15 min away.

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Spacious 3-BR Furnished Beach Home
Other holiday rentals with a pool

Peaceful suite in Boston with city views

Family & Friends Retreat

Modern and spacious 3Br 3Ba apartment assembly row

Luxe Amenitiesā¢Jacuzziā¢Airport Shuttleā¢

Beachfront apartment with city accessibility

Stylish and Cozy at Revere Beach

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

1 Bed Room Apt in Assembly Square
When is the best time to visit South Boston Waterfront?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £152 | £184 | £215 | £286 | £318 | £369 | £333 | £294 | £289 | £237 | £187 | £161 |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
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 £89 per night before taxes and fees

Verified guest reviews
Over 150 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 ā averaging 4.8 out of 5!

Nearby attractions
South Boston Waterfrontās top spots include Boston Children's Museum, Broadway Station and South Station Tower
Destinations to explore
- Flat rentalsĀ South Boston Waterfront
- Pet-friendly rentalsĀ South Boston Waterfront
- Rentals with outdoor seatingĀ South Boston Waterfront
- Rentals with a patioĀ South Boston Waterfront
- Rentals with a fireplaceĀ South Boston Waterfront
- Family-friendly rentalsĀ South Boston Waterfront
- Rentals with a washing machine and dryerĀ South Boston Waterfront
- Rentals with beach accessĀ South Boston Waterfront
- Fitness-friendly rentalsĀ South Boston Waterfront
- Rentals with poolsĀ Boston
- Rentals with poolsĀ Suffolk County
- Rentals with poolsĀ Massachusetts
- Rentals with poolsĀ United States
- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Freedom Trail
- New England Aquarium
- Boston Seaport
- MIT Museum
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Crane Beach
- Gillette Stadium
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- North Hampton Beach
- Onset Beach
- Prudential Center
- Roxbury Crossing Station
- Roger Williams Park Zoo




