Vacation rentals in Pleasure Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pleasure Bay

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

Guest favorite

Home in Cohasset

4.9 out of 5 average rating, 29 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

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

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

Apartment in Swampscott

4.89 out of 5 average rating, 104 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

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

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

Apartment in Beverly

5 out of 5 average rating, 21 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

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

Guest favorite

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

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.

Guest favorite

Guesthouse in Marshfield

4.98 out of 5 average rating, 80 reviews

Adorable 1 bedroom guest house with ocean view

Take it easy at this unique and tranquil getaway with an amazing ocean view. Enjoy the oversized deck for sunning, and grilling. 1 Queen bedroom and a pull out sleeper sofa in the family room with TV and WiFi. Kitchen includes basic appliances: mini-fridge, microwave, Keurig, toaster, toaster oven, air fryer, and portable cooktop. Amenities include use of sand volleyball court, linens and towels, window A/C, water toys, and 1 parking spot.