Vacation rentals in South Boston Waterfront

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Top-rated vacation rentals in South Boston Waterfront

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Guest favorite

A spacious rooftop deck is furnished with a light-colored wicker seating area and vibrant blue cushions. A matching coffee table sits at the center. The deck is surrounded by greenery and presents views of the neighborhood.

Apartment in East Boston

4.95 out of 5 average rating, 110 reviews

Luxury Penthouse w/ Private Roof Deck By The Ocean

Take in the beautiful skyline view as you have your morning beverage of choice, then take a relaxing stroll along the harbor walk 1 minute to the harbor 5 minute uber / 10 minute walk to airport 15 minutes to downtown Boston (by MBTA or uber) ON STREET PARKING: Only free 6P-8A and on the weekend. There is a $2.50 toll to drive into the city. Spot hero is a parking app that works great in Boston also. PARTIES: Not allowed. This is a family neighborhood. No loud music. Quiet hours after 9pm.

Guest favorite

A well-lit staircase with a wooden handrail leads upward. The walls are painted in a light color, enhancing the airy feel. A doorway at the top of the stairs reveals a bathroom with natural light filtering through a partially covered window.

Home in South Boston

4.92 out of 5 average rating, 394 reviews

3 BR Private Family Home, S. Boston/Seaport/BCEC

A beautiful, renovated single home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features luxurious amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

Guest favorite

A spacious deck features a patio sectional sofa and a dining table with high chairs. Potted plants adorn the railing, adding greenery. The wooden deck is arranged for relaxation and outdoor dining, providing a comfortable retreat with ample seating.

Apartment in South Boston

4.92 out of 5 average rating, 131 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.

Guest favorite

A modern kitchen features a large island with seating for three, situated adjacent to exposed brick walls. Stainless steel appliances are prominently displayed, complemented by white cabinetry and a sleek countertop. Natural light brightens the space, highlighting the warm wooden flooring.

Apartment in East Boston

4.97 out of 5 average rating, 154 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. Dive into our vibrant, 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 favorite

A serene beach scene features soft sand bordered by gentle grass, with two trees standing in the foreground. The water reflects a pastel sky at dusk, showcasing shades of pink and blue. Distant landmasses can be seen on the horizon.

Apartment in South Boston

5 out of 5 average rating, 84 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, 1.5 miles to BCEC! 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 property!

Guest favorite

Condo in Charlestown

4.98 out of 5 average rating, 128 reviews

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. Luxurious KING sized bed, work desk area, living room w/queen pull out bed, fireplace, fully equipped kitchen & priv deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in the house and NO smoking in courtyard. Not suitable for children under 6 years old.

Guest favorite

A modern shower area features sleek glass walls with hexagonal tiles, complemented by a decorative mosaic floor. A handheld showerhead and recessed lighting provide functionality, while neatly arranged towels hang nearby. The compact space is efficiently designed for convenience.

Condo in East Boston

4.96 out of 5 average rating, 250 reviews

CITY APARTMENT NEAR AIRPORT

🏙️ City Apartment Near Airport Station - New Listing! 🏙️ Experience luxury living in this private one-bedroom apartment, ideally situated just one block from the Airport Station. Enjoy easy access to Boston's vibrant attractions, including: Public Library: Just three blocks away, perfect for a quiet afternoon. Bremen's Park: A beautiful green space for relaxation and outdoor activities. Shopping Centers & Trendy Restaurants: Explore a variety of dining and shopping options nearby.

Guest favorite

An outdoor patio area features a wicker bench sitting on a brick-paved surface. A wooden railing surrounds the space, with a white privacy fence in the background. The area is partially shaded, providing a quiet place to relax.

Apartment in South Boston

4.86 out of 5 average rating, 123 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 favorite

A staircase leading to the upper level is framed by a vibrant mural depicting a ship on the water, featuring wooden crates at its base. A vintage mirror hangs on the wall, adding a decorative touch to the space.

Guest suite in South Boston

4.97 out of 5 average rating, 509 reviews

History BCEC Cruise Beach Pvt Bath/Entry King Bed

* *5 STAR ★★★★★ **No Chores! No To-Do List!** *Yes a Private Bathroom *Sparkling Clean and Sanitized *Historic and Charming home. *South Boston trendy neighborhood. *Dedicated Luxury Suite *Key-less Coded Access *King EuroTop Bed *Sitting area with 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 favorite

A narrow hallway features smooth hardwood flooring leading toward a living area at the end. On the left, a washer and dryer are visible, while a houseplant adds a touch of greenery against the wall. Natural light enters through a nearby window.

Guest suite in Back Bay

5 out of 5 average rating, 77 reviews

Cozy studio in Bay Village near Public Garden

This newly renovated private studio is ready to welcome you! This unit has 1 queen bed and 1 sleeper sofa, a desk, a kitchenette, a full bathroom, and a washer/dryer. It is the lower level of a historic 1800s Bostonian house, recently renovated. It has its own separate entrance. Great location! Conveniently located in Bay Village next to the Boston Public Garden, the studio is close to Downtown, Theater district, Chinatown, Beacon Hill, Back Bay, and South End!

Guest favorite

A cozy nook is featured with a small desk and an elegant chair, positioned by large windows with white blinds that allow natural light to filter in. A stylish lamp illuminates the space, while a hint of greenery is visible on the desk.

Condo in Beacon Hill

4.97 out of 5 average rating, 310 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 favorite

A traditional Chinese archway is seen at the entrance to a bustling Chinatown area, adorned with intricate carvings and a vibrant green roof. Shops and eateries line the streets, with pedestrians walking below the arch, highlighting the neighborhood's lively atmosphere.

Condo in Downtown Boston

4.97 out of 5 average rating, 164 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 queen size bed. There's also a side chair that converts to a chaise or a twin sleeper. 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.