Vacation rentals in South Boston Waterfront

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Top-rated vacation rentals in South Boston Waterfront

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

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Guest favorite

A bright four-season atrium features a large sectional couch, complemented by decorative pillows. Natural light floods the space through the glass ceiling and walls, illuminating the neutral tones of the furniture. A small black coffee table sits in front of the seating area.

Home in Cohasset

4.91 out of 5 average rating, 32 reviews

Village Colonial with Cohasset Harbor Views

Location!! An original Grand Dame of Historical Cohasset Harbor is just waiting for you to come and enjoy all that this historical sea side town has to offer. This newly reno/updated, 1848 village colonial has shows her glory with gorgeous hardwoods, fresh paint, comfortable and stylish decor that reflects the relaxed and beach town style of Cohasset. It has a fabulous third floor suite and a location that can't be beat! Harbor views from top two floors! 1 block to the harbor and walk to town.

Guest favorite

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Guest favorite

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.

Apartment in Winthrop

4.96 out of 5 average rating, 302 reviews

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.

Guest favorite

A child walks along a sandy beach, with waves gently lapping at the shore. The sky above features delicate wispy clouds against a bright blue backdrop. In the distance, beachgoers enjoy the water, and charming coastal houses line the beach.

Apartment in Hull

4.96 out of 5 average rating, 68 reviews

Anchors Away Inn Cozy Walk to Beach, Courtyard

A minute walk across the street to your private beach. Walk on picturesque Cadish Ave to Marina and Local 02045. Drive 5 mins to Kenberma shops. A 7 minute drive to main beach restaurants and bars. Comfy Beds and Bamboo linens. Outdoor shower, private backyard with Lg fire pit and large courtyard with string lights and seating. New AC, Fast-Wifi, dedicated workspace. Dining table for 4 plus a Coffee Bar and a snack or two. Comfortable shower with a seat. Pack & play crib, high chair and games.

Guest favorite

A sandy beach extends along a calm ocean, where gentle waves lap at the shore. Rocky formations are visible in the water, and a clear blue sky overhead enhances the serene coastal view.

Home in Scituate

4.95 out of 5 average rating, 20 reviews

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Top guest favorite

An expansive view of the harbor is captured, showcasing numerous sailboats anchored in the water. Lush green grass and wooden benches frame the scene, with a flagpole standing nearby. A large tree casts shade on the area, contributing to a peaceful atmosphere.

Condo in Lakeside Marblehead

4.99 out of 5 average rating, 174 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

Top guest favorite

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

4.98 out of 5 average rating, 377 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Superhost

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

4.87 out of 5 average rating, 108 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Top guest favorite

A modern living space features a green velvet sofa adorned with decorative cushions, paired with a circular dining table and sleek black chairs. The area is enhanced by a large area rug and a striking wall design, while large windows provide natural light and water views.

Apartment in Beverly

5 out of 5 average rating, 32 reviews

#1 Top Flr Waterview|Lux Design|Pvt Balcony

Experience luxury in this top-floor apartment with stunning water views. Enjoy air conditioning, a private balcony, plush linens, and a custom desk with wireless monitor. Free off-street parking included. Centrally located, you're steps from restaurants and a short walk to the train station for easy access to Boston. Perfect for a serene getaway or productive stay, with Salem's historic charm just minutes away. Book now for a blend of comfort, convenience, and coastal beauty!

Superhost

A modern kitchen space features sleek cabinetry and a marble countertop with bar seating for two. Natural light filters through a nearby window, illuminating an artistic water-themed wall piece. A pendant light hangs above the bar, enhancing the clean design.

Apartment in Lakeside Marblehead

5 out of 5 average rating, 3 reviews

Captains Qs 2 bed, downtown MHD sleeps 4, parking

‘Captain’s Quarters’ New! In the heart of Historic Old Town Marblehead. Situated close to Maddies, the Landing, shopping and right next to the Driftwood diner, for the best breakfasts and fried dough on the weekends! Steps to the harbor where you can easily access local yacht clubs and a Public launch service is available for Harbour tours. Prime parking, AC, a fresh modern clean space and amenities will provide you with a very relaxing stay in our beautiful seaside town

Superhost

Apartment in Brighton

4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

Experience Boston in a 1 bedroom with comfortable decor and charming feel! Just a 5 min walk from the T and close to Boston College/Harvard/MIT, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 55” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed -> Balcony Ideal for business travelers, couples, nurses, and anyone looking to experience Boston in peace and comfort.

Top guest favorite

A bright bedroom features a spacious bed dressed in crisp white linens. Three windows offer panoramic views of the water, allowing natural light to fill the space. A white shelving unit stands to the side, enhancing the room's functionality.

Home in Hull

4.95 out of 5 average rating, 21 reviews

Every room a water view updated kitchen & bath

Make some memories at this unique and family-friendly place. 5 minute walk to commuter boat/ferry to Boston, Ma/Logan airport. Ferry ride is 15-30 minutes depending if boat is direct to Boston, MA or stops at Logan or Hingham. Please check ferry schedule as it changes to weekday only in the off season. The house is 28 miles south of Boston. Panoramic water views. Beach access across the street. Vacation or work from home with water views from every window.

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What guests are saying

Entire House: Home Away Home

5 out of 5 average rating, 19 reviews3 weeks ago

My two adult children and I stayed here with our two dogs while my wife was having surgery in Boston. The location was great. Car ride to the Longwood medical area was about 25 minutes. The neighborhood consists of single family homes on small lots, not at all fancy but entirely safe as far as we could tell. We were just a few short blocks from a school playing field where leashed dogs were welcome, and other dog-walkers were often on the street in the morning and evening. The house is a bit quirky. There is no seating in the kitchen, but the dining area is very spacious although located down a short hallway from the kitchen. Each of the three bedrooms was more than ample and very quiet at night. We slept well. As we stayed more than a week we were grateful that laundry facilities were present in the basement. Roosevelt was an excellent host and quick to respond to my requests. I would definitely stay in his place again should a similar situation arise.

Home in West Newton

What guests are saying

Connected Apartments: walk to town & ocean park

4.83 out of 5 average rating, 6 reviews9 months ago

We had a wonderful stay at this peaceful cottage in a beautiful seaside town. House was very comfortable and clean. The whole town is walkable so you can easily get to restaurants, coffee, groceries etc. Having 2 joined suites worked wonderfully so that our teenagers could have their own space while still being connected to us. Our family had a wonderful time!

Home in Lakeside Marblehead

What guests are saying

Charming condo steps from beach

4.86 out of 5 average rating, 14 reviews1 month ago

I can’t rave enough about how wonderful our stay was. Casie was absolutely great. She made sure our stay was perfect from the beginning to the end. The location is amazing. There are restaurants and the beach that are walking distance. Winthrop is a true gem! We are looking forward to coming back and staying here again!

Apartment in Winthrop

What guests are saying

Elegant home in historic Marblehead.

4.91 out of 5 average rating, 45 reviews1 week ago

In a sea of Airbnb’s that are soulless money makers for owners, this home is a gem — and a real nod to what the concept of home sharing is about. This is a beautiful home —- appointed perfectly, clean as can be, comfortable, peaceful and clearly loved and cared for by its owner, Eileen. Marblehead is such a stunning place but to have such a fantastic place to call home for a few days made this one of our favorite trips. Very lucky that Eileen makes this home available for guests to enjoy. Thank you again!!!

Home in Lakeside Marblehead

What guests are saying

Luxury Sand Castle Beach House Historic SALEM

4.91 out of 5 average rating, 11 reviews4 months ago

Gary provided an amazing experience during our stay! The home was spotless, beautifully decorated, and equipped with everything we needed for a comfortable visit. The location was perfect, close to main attractions, yet peaceful and relaxing. Gary was incredibly thoughtful and responsive, making us feel right at home. Small touches like a welcoming Thanksgiving card and chocolates really stood out. We couldn’t have asked for a better place to stay and would absolutely recommend this Airbnb to anyone visiting the area. We hope to return soon! Thank you for the exceptional hospitality!

Condo in Salem

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