Vacation rentals in South Boston Waterfront

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Top-rated vacation rentals in South Boston Waterfront

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Top guest favorite

An inviting brownstone entrance features a wooden door with decorative glass, framed by large planters filled with colorful flowers. Two tall windows with black shutters are positioned above a stone staircase, enhancing the charming urban setting.

Apartment in Boston

4.99 out of 5 average rating, 243 reviews

Astonishing 1 Bed South End Boston's Best Location

Clean, unique, bright, inviting, 1-bedroom on the 1st floor. Newly renovated with astonishing ceilings, new tall custom windows, new appliances. The best of Boston outside your door Located half a block to Restaurant Row, where you’ll find some of the best dining in the city. Famous bakeries, coffee shops are all near, a super effortless walk to the very BEST Boston has to offer. Complimentary Keurig coffee, snacks, Netflix, movie channels, high speed internet. It doesn't get better than this!

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, 108 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, 393 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

4.93 out of 5 average rating, 127 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 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

A modern kitchen features a spacious island with four padded stools. Sleek cabinetry with wood accents is complemented by stainless steel appliances, including a refrigerator and microwave. Illuminated pendant lights hang above the island, enhancing the functional yet stylish space.

Condo in East Boston

4.93 out of 5 average rating, 151 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

Guest favorite

The exterior of the farmhouse-style home features a welcoming porch supported by white columns. A vibrant display of orange roses flourishes in the flower bed, while an American flag gracefully waves above. Sunlight illuminates the scene, enhancing the inviting atmosphere.

Apartment in South Boston

4.97 out of 5 average rating, 193 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 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, 121 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

Guest suite in South Boston

4.97 out of 5 average rating, 506 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

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, 309 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.

Superhost

A tranquil scene features a reflective body of water surrounded by trees adorned with vibrant autumn foliage. City buildings rise in the background, contrasting with the natural landscape, while the blue sky is mirrored in the water, creating a harmonious blend of nature and urban architecture.

Apartment in Beacon Hill

4.82 out of 5 average rating, 324 reviews

Beacon Hills Studio next to State house 3

Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.Take it easy at this unique and tranquil getaway.