Vacation rentals in Pleasure Bay

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Top-rated vacation rentals in Pleasure Bay

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

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Guest favorite

A scenic harbor view showcases numerous fishing boats gently resting on calm waters. The landscape features a distant tree line under a clear blue sky, contributing to a serene coastal atmosphere.

Home in Cohasset

4.9 out of 5 average rating, 30 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

Apartment in Winthrop

4.96 out of 5 average rating, 301 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 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, 19 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.

Guest favorite

A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.

Apartment in Salem

4.98 out of 5 average rating, 374 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.

Guest favorite

A private wrap-around porch is shown, featuring a wooden dining table with matching chairs. Sunlight filters through, illuminating the surrounding neighborhood with cozy homes and greenery visible in the background. The space is complemented by a decorative plant on the table.

Apartment in Swampscott

4.9 out of 5 average rating, 105 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.

Guest favorite

The oceanfront house features a spacious wraparound balcony supported by sturdy pillars, providing views of the sea. The exterior showcases a combination of textured gray siding and large windows. A rocky shoreline is visible in the foreground, with clear blue skies above.

Home in Scituate

5 out of 5 average rating, 25 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!

Guest favorite

The seaside house is visible against a backdrop of a vibrant sky, showcasing soft pastel hues of pink and blue. Lush green lawns surround the house, with outdoor seating arranged in the foreground. The historic character of the structure is highlighted with its traditional windows and inviting facade.

Home in Scituate

4.96 out of 5 average rating, 25 reviews

*Location & Views* Walk to Beaches & Harbor Town

This charming, renovated 1910 seaside house is on a hilltop in quaint & historic Scituate, offering wide-ranging water views of the harbor and open ocean. It’s ideal for families or a group of friends. This relaxing coastal home is well-laid out, well-appointed, & within a 5min walk to all of Scituate Harbor’s cafes, restaurants, shops, movie theater, & grocery. Peggotty, Museum, & First Cliff beaches are all within walking distance (~0.7 miles), as is Scituate’s historic lighthouse.

Guest favorite

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

5 out of 5 average rating, 25 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 bright living area features a comfortable white sofa adorned with accent pillows. A small white coffee table is positioned in front, accompanied by a decorative item. A large piece of colorful wall art and natural light from the window enhance the welcoming space.

Apartment in 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

A beach-style bungalow features a welcoming porch with steps leading to the entrance. A white picket fence surrounds the property, with a gravel path and grassy areas visible. Surrounding trees provide shade, creating a relaxing outdoor ambiance.

Home in Scituate

4.83 out of 5 average rating, 58 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!

Guest favorite

The exterior of the coastal rental features a charming two-story building with light-colored siding and black shutters. A well-maintained lawn and colorful garden beds surround the property, while an American flag adds a welcoming touch to the front entrance.

Home in Scituate

5 out of 5 average rating, 20 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!

Guest favorite

A three-story house is depicted, showcasing a light-colored exterior and a welcoming front porch. Grassy beach access is visible in the foreground, and power lines extend across the skyline, adding a unique perspective to the coastal setting.

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.