Vacation rentals in South Boston Waterfront

Home in Lakeside Marblehead

5 out of 5 average rating, 13 reviews

Charming antique in historic seaside beach town

Built in 1840, this historic home is loaded with character! Charming beamed ceilings, fireplaces, and wide-pine floors are coupled with contemporary stylish decor and all the modern conveniences. Located downtown, you can walk to restaurants, shops, the movie theater and historic Old Town. The patio, deck & tiered backyard offer a private oasis and options for outdoor dining and lounging. Explore the many beaches and harbor on foot. Nearby beaches boast a playground, a cafe and paddle boarding.

4.91 out of 5 average rating, 32 reviews

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

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.

Superhost

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

4.97 out of 5 average rating, 266 reviews

The charming entrance of the cottage is framed by vibrant greenery and colorful flowers. Two wooden chairs are positioned in front of the entrance, welcoming guests. A decorative flag flutters above the door, completing the inviting scene.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.96 out of 5 average rating, 308 reviews

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

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.

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.

4.95 out of 5 average rating, 22 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.

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

4.86 out of 5 average rating, 113 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.

An oceanfront balcony offers a spacious wooden deck featuring several high-top chairs and tables, providing an ideal spot to enjoy the coastal views. The serene ocean can be seen in the distance, complemented by a subtle gray color palette of the flooring and building exterior.

5 out of 5 average rating, 27 reviews

Oceanfront-Harbor View Home

Welcome to your ultimate oceanfront getaway in Scituate, Massachusetts! Nestled at the tip of a picturesque peninsula, this Airbnb is a dream destination for those seeking a coastal retreat. With breathtaking views of the ocean, a neighboring historical lighthouse, and a bustling harbor, this home promises an unforgettable vacation. Experience unmatched sunset views and the quaint shops and delicious eateries in the harbor town a mile away. Book now and create lasting memories by the sea!

5 out of 5 average rating, 34 reviews

A private balcony features two dark wood chairs positioned for optimal views of the surrounding landscape. The scene captures the expanse of water in the distance, framed by a cloudy sky. An urban setting is visible below, highlighting the coastal charm.

Apartment in Beverly

#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

The image captures a serene beachfront with gentle waves lapping against sandy shores. Rocks line the edge of the beach, while a clear blue sky stretches overhead, merging with the tranquil sea. The distant coastline features various structures, enhancing the scenic view.

4.84 out of 5 average rating, 61 reviews

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

5 out of 5 average rating, 22 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!