Holiday houses in South Boston Waterfront

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Top-rated holiday rentals in South Boston Waterfront

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious sleeping area features a king bed with a plush white duvet and decorative pillows. Warm light is provided by bedside lamps, while a colorful rug adds texture to the wooden floor. A decorative door, showcasing a lighthouse scene, leads to another room.
Guest suite in South Boston
4.97 out of 5 average rating, 555 reviews

One by Land BCEC History-Cruise- PVT Bath/Entry

*5 STAR ★★★★★ *Distinctive Suites **No Chores! No To-Do List!** *Sparkling Clean and Sanitized *Yes a Private Bathroom *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *Dedicated Luxury Suites *Key-less Coded Access *King EuroTop Bed *Edloe Finch Sofa *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking. Paid parking located at: 12 Drydock Ave, Boston, MA 02210

Top Guest favourite
A spacious bedroom is furnished with a wooden bed featuring a floral-patterned duvet. Decorative cushions add a pop of color. Natural light filters through a large window adorned with blue curtains, illuminating the warm wooden floor and creating a cozy ambiance.
Apartment in Boston
4.87 out of 5 average rating, 125 reviews

Walk! Walk! Kenmore Square - 2 Beds / 1 Bathroom

2 beds / 1 bathroom apartment in the middle of everything! Located right in Kenmore Square, steps from subway station and Famous Citgo Sign. Walking distance to Fenway Park, Back Bay, restaurants, bars, and more! Walk walk walk everywhere! Next to Boston University and in front of Charles River Esplanade. Very close to Downtown, Cambridge, Longwood Medical Area, supermarkets, and way so many cool places! Includes everything you'll need for your stay. Super safe and convenient neighborhood! :)

Top Guest favourite
An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.
Apartment in South Boston
4.99 out of 5 average rating, 109 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Top Guest favourite
A bright bedroom features a spacious bed with light bedding and decorative pillows. Two large windows allow natural light to illuminate the room. A cozy armchair and a nightstand with lamps enhance the comfort, while a subtle area rug adds warmth to the hardwood floor.
Apartment in South Boston
4.92 out of 5 average rating, 173 reviews

2 BDR/2b- walk to Seaport & BCEC

We welcome you to stay at our stylish apartment in South Boston (Southie)! Located next to West Broadway, South Boston’s main road with plenty of restaurants, coffee shops, groceries, and boutique stores. Located walking distance to the Seaport District, Convention Center (BCEC), and our local Southie beaches. The space is ideal for travelling professionals, small families, couples, and those looking for a true neighborhood experience, tucked away just minutes from all the big city attractions.

Superhost
A well-lit bedroom features a spacious bed dressed in crisp white linens, flanked by small bedside tables with lamps. Large windows provide natural light and views of the surrounding area, while the soft blue walls create a calming ambiance.
Condo in South Boston
4.87 out of 5 average rating, 123 reviews

Penthouse 2 Beds /2 Baths luxury in South Boston

Kick back and relax in this calm, stylish space. You won’t even feel like you are in the center of the city . Everything you need is within a walking distance , bars , coffee shops and many restaurants to choose from. Top floor unit, private balcony with 2 full bedrooms & 2 full bathrooms on opposite sides of the house makes traveling in groups much more comfortable. Brand new build 2023 , this is a hotel like stay professionally managed but with the comfort of a home away from home

Top Guest favourite
A modern kitchen is showcased with light wood cabinetry and an expansive island featuring a white marble countertop. Pendant lights hang above, illuminating the space. The open layout leads to a cozy living area with a large sectional sofa, surrounded by windows that invite natural light.
Condo in East Boston
4.94 out of 5 average rating, 193 reviews

Luxury apt w/ sauna & deck | by airport, downtown

Welcome to your private oasis just minutes away from Logan Airport AND Boston's bustling streets. Start your day with a walk along the water, then enjoy all that Boston has to offer right nearby. 1 min. walk to the waterfront 5 min. walk to Logan Airport 10 min. Uber (or 1 MBTA stop) to Downtown Boston PARKING IS DIFFICULT: - If you’re coming during the week, parking can be hard to navigate - If you MUST bring a car, do not arrive in the evening or you may not find a spot

Top Guest favourite
A light-filled interior features a wooden dining table positioned near a decorative fireplace. The walls are painted in soft blue, creating a calm setting. A glimpse of a modern kitchen is visible in the background, and a framed artwork adds a touch of character.
Apartment in South Boston
4.96 out of 5 average rating, 237 reviews

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Guest favourite
A well-lit bedroom features a spacious bed with white bedding and decorative pillows. A bedside lamp stands next to the bed, and a window is dressed with long gray curtains. A mirror reflects the room's light, enhancing the sense of openness.
Apartment in South Boston
4.89 out of 5 average rating, 175 reviews

Cozy suite in the city!

Enjoy a stylish experience at this centrally-located place in an extremely vibrant neighborhood of Boston. While staying at the AIRBNB, you will be in close proximity to the BCEC if you are in town for work. If you are in town for a pleasure, you will be very close to Downtown Boston, Fenway Park, the Seaport District, Faneuil Hall and the historic North End. You’ll be pleasantly surprised of how easy public transportation is to navigate around the city from the AIRBNB.

Guest favourite
A scenic view of the city skyline is captured from a waterfront promenade, with bright sunlight reflecting off the water. A curved brick pathway leads towards the railing, showcasing the expansive skyline of modern buildings in the distance.
Apartment in East Boston
4.96 out of 5 average rating, 189 reviews

Nxt to ocean, 5 min dntwn by T

Embark on an urban escape! Immerse yourself in our chic 2BR/1B + office retreat, ideal for up to 4 guests. Enjoy fast WiFi, steps away from an oceanfront park with stunning Boston skyline views. Walk to the Blue Line T station, one stop to downtown or the airport. Safe, historic neighborhood with restaurants, bars, yoga, sailing, and galleries. Not suitable for children, NO PARKING/pets/smoking/cannabis/parties. Make this urban oasis your next unforgettable getaway!

Top Guest favourite
The living room features a dark sofa with teal accent pillows, complemented by a wooden coffee table. A light fixture hangs from the ceiling, and natural light fills the space through large windows. A small dining table with two chairs is visible, enhancing the cozy layout.
Condo in Beacon Hill
4.97 out of 5 average rating, 340 reviews

Gorgeous Beacon Hill 1BR | 1BA

Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

Guest favourite
A studio space features a spacious bed with a memory foam mattress and a queen pull-out sofa. A modern kitchen is visible, complemented by a dining area with high stools. Natural light enters through a window, while artwork adds visual interest to the walls.
Condo in East Boston
4.83 out of 5 average rating, 304 reviews

Stylish garden level studio with a private patio

Enjoy your stay in this stylish East Boston garden level studio with a private back patio. It is centrally located near restaurants, the waterfront, a running & biking trail, the airport, public transportation, and it is 1 metro stop away from downtown Boston. The metro stop, Maverick, is a 4 minute walk! The studio is equipped with a king bed that has a memory foam mattress, a queen pull out sofa, and a fully equipped kitchen.

Top Guest favourite
A pair of large, double doors with a rich, textured surface stands prominently in the background. The doors are flanked by warm, wooden floors and a light-colored sofa adorned with decorative pillows. A vibrant area rug adds color to the setting.
Condo in Downtown
4.97 out of 5 average rating, 186 reviews

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area-queen bed, also sofa in living room can become a pull-out double size bed. The bathroom is with shower and tub, a complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

Popular amenities for South Boston Waterfront holiday rentals

When is the best time to visit South Boston Waterfront?

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Avg. price$304 NZD$359 NZD$357 NZD$379 NZD$433 NZD$506 NZD$518 NZD$503 NZD$498 NZD$423 NZD$372 NZD$355 NZD
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Quick stats about holiday rentals in South Boston Waterfront

  • Total holiday rentals

    Explore 170 holiday rentals in South Boston Waterfront

  • Nightly prices starting at

    South Boston Waterfront holiday rentals start at $66 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    170 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

  • 4.7 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