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Vacation rentals in Pleasure Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pleasure Bay

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Guest favorite
Private room in Boston
4.83 out of 5 average rating, 166 reviews

Comfortable Boston Bedroom 03

This beautiful Boston private bedroom is outfitted with a queen sized Casper mattress, Casper pillows, hypoallergenic bedding, free wifi and digital door lock. This space also has a shared kitchen, shared living room and shared bathroom with all the amenities needed to feel at home. NO PARTIES, NO EVENTS, NO DRUGS On the morning of your arrival the full check-in instructions will be sent, including all codes to make your self check-in process seamless. Our space is perfect if you want to be close to the heart of the City: Walk Score: 88 Logan Airport: driving: 15 mins | transit: 43 mins Downtown Boston: driving: 15 mins | transit: 30 mins South Bay Center (Movie theater, Nike Town, Target, plenty of shopping): driving: 5 mins | transit: 11 mins Dorchester Brewery: driving: 5 mins | transit: 11 mins Boston Children’s Hospital: driving: 15 mins | transit: 30 mins Brigham and Women’s Hospital: driving: 15 mins | transit: 30 mins Boston Medical Center: driving: 10 mins | transit: 25 mins Northeastern University: driving: 10 mins | transit: 22 mins Boston University: driving: 16 mins | transit: 43 mins Public Transportation (from apartment): SAVIN HILL STATION (red line): Driving: 0.8 miles | 1.3 km | 4 mins Walking: 0.7 miles | 1.13 km | 15 mins 125 Savin Hill Ave, Dorchester, MA 02124 UPHAMS CORNER STATION (Franklin Line/Foxboro): Driving: 0.6 miles | 0.97 km | 3 mins Walking: 0.6 miles | 0.97 km | 13 mins 691 Dudley St, Dorchester, MA 02125 BUS STOP: BUS #15: stops right down the street and northbound takes you to Ruggles Stations (orange line) or southbound takes you to Fields Corner Station (red line). BUS #17: stops right down the street and northbound takes you to Andrew Station (red line) or southbound takes you to Fields Corner Station (red line). Public Transportation (from apartment): SAVIN HILL STATION (red line): Driving: 0.8 miles | 1.3 km | 4 mins Walking: 0.7 miles | 1.13 km | 15 mins 125 Savin Hill Ave, Dorchester, MA 02124 UPHAMS CORNER STATION (Franklin Line/Foxboro): Driving: 0.6 miles | 0.97 km | 3 mins Walking: 0.6 miles | 0.97 km | 13 mins 691 Dudley St, Dorchester, MA 02125 BUS STOP: BUS #15: stops right down the street and northbound takes you to Ruggles Stations (orange line) or southbound takes you to Fields Corner Station (red line). BUS #17: stops right down the street and northbound takes you to Andrew Station (red line) or southbound takes you to Fields Corner Station (red line).

Guest favorite
Private room in Boston
4.84 out of 5 average rating, 891 reviews

Shelly's Swan Room

A cozy room & warm welcome in a restored historic Boston HOME. Shared common space. Hosts live downstairs-- a PERFECT place for a PRE-FLIGHT OVERNITE, a LATE NIGHT ARRIVAL, or a safe BASE to explore ALL Boston offers! NOOO CLEANING FEES ADDED 100 yds. to Subway! 8 mins. to/from Logan Airport, 10 mins. into downtown Boston. A PERFECT SPOT for airport STOP-OVERS $20 charge for EXTRA guest FREE, Safe on-street PARKING FULL USE KITCHEN BAG STORE BEFORE AND AFTER Sorry, no children under 7 years

Top guest favorite
A spacious sleeping area features a king bed with a plush white duvet and decorative pillows. Warm light is provided by bedside lamps, while a colorful rug adds texture to the wooden floor. A decorative door, showcasing a lighthouse scene, leads to another room.
Guest suite in Boston
4.97 out of 5 average rating, 546 reviews

One by Land BCEC History-Cruise- PVT Bath/Entry

*5 STAR ★★★★★ *Distinctive Suites **No Chores! No To-Do List!** *Sparkling Clean and Sanitized *Yes a Private Bathroom *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *Dedicated Luxury Suites *Key-less Coded Access *King EuroTop Bed *Edloe Finch 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
Private room in Boston
4.86 out of 5 average rating, 640 reviews

Large Private Bedroom & Bathroom by the Seaport

This is the original master bedroom in a single family home in South Boston. The private room is quite spacious with walk-in closet, Queen size bed, mini-fridge, ceiling fan, A/C & heat. There is a bathroom right outside the room that is for your private use. Please note parking is not included but there is street parking in the area. The house is close to several popular local restaurants and bars in the area. Perfect spot if you are going to the Boston Convention Center and the Seaport area.

Guest favorite
An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.
Apartment in Boston
4.99 out of 5 average rating, 104 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Top guest favorite
Private room in Boston
4.96 out of 5 average rating, 452 reviews

219 on the Ocean with Private Bath

An old Boston home in Savin Hill. My place is close to The T, overlooks Malibu and Savin Hill Beaches, easy to get here from the airport, and easy to get downtown. We are close to restaurants, the JFK Museum, and the Harbor-walk. You’ll love my place because of the quiet and beauty. You will have your solitude and privacy. My place is good for solo adventurers, business travelers, medical people. All walks of life welcomed here. Registered with the City of Boston #STR383505

Guest favorite
A light-filled interior features a wooden dining table positioned near a decorative fireplace. The walls are painted in soft blue, creating a calm setting. A glimpse of a modern kitchen is visible in the background, and a framed artwork adds a touch of character.
Apartment in Boston
4.96 out of 5 average rating, 220 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

Top guest favorite
A well-lit bedroom features a spacious bed with white bedding and decorative pillows. A bedside lamp stands next to the bed, and a window is dressed with long gray curtains. A mirror reflects the room's light, enhancing the sense of openness.
Apartment in Boston
4.89 out of 5 average rating, 168 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
Private room in Boston
4.93 out of 5 average rating, 522 reviews

AKBrownstone: modern treetop skyline view by T

🏠 Live like a local: designed bedroom, in a classic Boston Brownstone 🚾 Frequently professionally maintained home, clean shared bathroom 🚇 5 mins walk to the T (Orange Line Subway), 3 stops to city center 👣 Walk to Longwood Medical Area, Museum of Fine Arts, Northeastern, & Fenway Park 🌳 Sunny west/north windows looking over the treetops & partial city skyline 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Guest favorite
Private room in Boston
4.96 out of 5 average rating, 251 reviews

A bit of France in Boston

Historic family-owned 1885 Victorian (not a hotel) in quiet area, walking distance to public transportation (Commuter Rail, Red Line T, Bus). Car parking available. Clean & ecological living in a bedroom, with armoire, chairs & table. Organic cotton futon & bedding w/ down comforters. Air mattress available. Shower w/ water filter, ecological soaps. Perfect for a busy day touring or working. Organic Breakfast & dinner available for a fee.

Top guest favorite
A spacious living area is furnished with a dark sofa, a decorative wall art piece, and a round coffee table. Bar stools are positioned near the kitchen, which is visible in the background. Natural light enters through windows covered by green curtains.
Apartment in Boston
4.93 out of 5 average rating, 421 reviews

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

Top guest favorite
Private room in Boston
4.86 out of 5 average rating, 241 reviews

Private Room 3 Min Walk to Savin Hill Subway Stop

A beautiful Victorian house in Savin Hill neighborhood of Dorchester. 3 minutes walk to Savin Hill Red Line station. Convenient commute to Broadway, South Station, Boston Commons, Downtown, MGH, Harvard Square along the Red Line. hardware floor, private bedroom, gas stove kitchen available, 10 minutes walk to the beach, quiet neighborhood. I'm a male professional working in Boston. My home is open to nice and respectful guests.

Popular amenities for Pleasure Bay vacation rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Pleasure Bay