Holiday rentals with a pool in South Boston Waterfront

Find and book unique homes with a pool on Airbnb

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

  • Total holiday rentals

    Explore 60 holiday rentals in South Boston Waterfront

  • Nightly prices starting at

    South Boston Waterfront holiday rentals start at $152 SGD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    60 of South Boston Waterfront holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    South Boston Waterfront stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

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

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.

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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, 346 reviews

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

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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, 448 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)

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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, 284 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.

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Guest favourite
Home in Canton
4.76 out of 5 average rating, 38 reviews

Luxury lake retreat- pool, fire pit, trails

A spacious private retreat in nature, on a lake with trails at your door, yet minutes to major highways and easy access to Boston. Grand suite: king bed, air bed, and 2 twin beds with private half bath Bonus Room with twin bed, washer & dryer Star Wars Room with queen bed 3 Spa-like bathroons with walk-in showers, plus Jacuzzi. Gourmet kitchen Beautiful shared backyard with private deck, BBQ grill, in-ground pool (May–August), fire pit, seating areas, and trails right outside your door!

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Superhost
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
4.95 out of 5 average rating, 161 reviews

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite 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 -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

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Guest favourite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guest house in West Roxbury
4.95 out of 5 average rating, 217 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

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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
4.87 out of 5 average rating, 114 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.

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Guest favourite
A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.
Home in Arlington
4.93 out of 5 average rating, 58 reviews

Beautiful Spacious 4BRM House!

A thoughtfully cared-for New England home best suited for a quiet, comfortable stay in a residential neighborhood. Enclosed back yard with pool during summer (June 21 - September 20) 4 bedrooms (2 ensuite), 3 full bathrooms, 1 half bath. Spread over 2 floors: - Floor 1: eat-in kitchen, 1/2 bath, living, dining, office - Floor 2: 4 bedrooms, 3 bathrooms, bonus room - Has STAIRS to bedrooms Outside: Yard, unheated swimming pool (summer 6/21-9/20), patio. 2 off-street parking.

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Top guest favourite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston
4.97 out of 5 average rating, 120 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...

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Guest favourite
A bright living area features two mustard-colored sofas arranged around a marble-top coffee table. Large windows provide a view of the city, allowing natural light to illuminate the space. A modern lamp and a wooden floor lamp complement the contemporary design.
Flat in Fenway-Kenmore
4.85 out of 5 average rating, 34 reviews

Luxury 2BR 2BA Condo Fenway Boston Washer&Dryer in

spacious and stylish apartment located in Fenway will be your conductor in Boston experience. This apartment is a corner unit and is spread across one floor only. Few steps to BU campus. Very close to most important hospitals Boston children's hospital, Dana Farber cancer insitute, & Brigham & women etc.. Guests have access to the communal amenities within the apartment building: Rooftop terrace with a pool, working spaces, dog spa/run, fitness center, and yoga studio.

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Top guest favourite
Apartment in Cambridge
4.93 out of 5 average rating, 27 reviews

“Luxury 2BR Cambridge | Pool + Parking”

Two blocks from Lechmere Station, with the Green Line running direct to Kendall Square, MIT, and Harvard, this residential 2BR/2BA operates on a different standard than corporate hotel rooms. On-site garage parking runs the elevator straight to your floor, unlimited in-and-out, versus $50-65/night at nearby garages that re-bill on every return. Two full bathrooms, in-unit laundry, a fully equipped kitchen, and shared pool access. Sleeps 5.

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Superhost
Flat in Chelsea
4.82 out of 5 average rating, 83 reviews

Cozy 1BR Near Boston w/ Pool & Gym

🌟 Features You’ll Love • 1BR w/ king bed • Fast Wi-Fi + workspace • Smart TVs • Full kitchen • Washer/dryer • Private patio • Private parking • Pool, gym, game room & business lounge 📍 Prime Location • Chelsea, minutes from Boston ✨ Perfect For • Business travelers, travel nurses & city stays 💫 Good To Know • Strictly non-smoking Dont miss out- reserve your stay today and enjoy a memorable Boston experience.

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Popular amenities for South Boston Waterfront rentals with a pool

When is the best time to visit South Boston Waterfront?

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Avg. price$323 SGD$326 SGD$409 SGD$490 SGD$471 SGD$598 SGD$571 SGD$505 SGD$497 SGD$408 SGD$321 SGD$276 SGD
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