Vacation rentals in Pleasure Bay

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Top-rated vacation rentals in Pleasure Bay

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Superhost
Private room in Boston
4.8 out of 5 average rating, 176 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).

A modern living area showcases an open layout with a comfortable seating arrangement. Natural light fills the space through large windows. A dining table is set nearby, complemented by stainless steel appliances in the kitchen. Decorative elements enhance the overall design.
Apartment in Boston
4.91 out of 5 average rating, 309 reviews

Swanky unit Convenient to Downtown nr Restaurants

My Swanky pad is a modern renovated garden level unit with a great open layout. Is very clean, comfortable, has private entrance, high ceilings, large windows which project great natural light into the space. Consist of: -- Kitchen w. Dining Space (work space) --Stainless steel appliances, full stove, refrigerator & over the range microwave --Keurig Coffee ( Complimentary coffee ), Electric hot water kettle --Large closets --55" Smart Tv in living room --High Speed WIFI --Full Bath with Tub

Guest favorite
Private room in Boston
4.87 out of 5 average rating, 645 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.

Top 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, 107 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
An open-concept living area showcases a modern kitchen with white cabinets and stainless steel appliances. A dining table is positioned adjacent, with seating for four. Comfortable seating is provided by a light-colored sofa and stylish chairs, complemented by a textured area rug.
Condo in Boston
4.96 out of 5 average rating, 108 reviews

Modern Luxury | Free Parking, Near T | Home Cinema

Welcome to our stylish East Boston condo! Just a 5-minute walk to the Blue Line and 11-minute drive (or 25-min walk) to Logan Airport. Only two blocks from the waterfront with stunning Boston skyline views. This modern farmhouse retreat features two cozy bedrooms plus two more beds downstairs. The sleek kitchen and dining area are great for meals or morning coffee. Relax in the comfy living room or enjoy movie nights on the 135-inch home theater. Includes in-unit laundry and off-street parking.

A compact efficiency unit features a twin size day-bed dressed in soft linens, flanked by decorative pillows. A small dining table and two chairs are positioned nearby, with natural light filtering through a window adorned with light curtains. Artistic wall decor enhances the cozy atmosphere.
Apartment in Boston
4.91 out of 5 average rating, 32 reviews

Sunlit Efficiency Unit-Longwood/Fenway

Discover comfort and convenience in our compact efficiency unit located steps away from many popular restaurants, world-renowned hospitals, tourist attractions & universities. We're a 2 minute walk to the Fenwood Green line Subway, 1 mile to Fenway Park, and 0.4 miles to Longwood Medical. We're less than 1 mile from Museum of Fine Arts and the Isabella Gardner Museum. Some of the cities best attractions are located 1-2 miles from us; Prudential, Boston Common, Newbury St, Chinatown & more!

Guest favorite
A spacious suite features a king EuroTop bed adorned with decorative pillows. A gray sofa with colorful accent pillows and a dark coffee table complement the room. Natural light enters through two windows, with light-colored curtains framing them. An eclectic rug adds warmth to the wooden floor.
Guest suite in Boston
4.96 out of 5 average rating, 532 reviews

Two by Sea BCEC Cruise History Pvt Bath/Entry King

* *5 STAR ★★★★★ **No Chores! No To-Do List!** *Yes a Private Bathroom *Sparkling Clean and Sanitized *Historic and Charming home *Luxury and Comfort *South Boston trendy neighborhood. *Dedicated Luxury Suite *Key-less Coded Access *King EuroTop Bed *Sitting area with 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

Top guest favorite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 994 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Guest favorite
A modern kitchen features sleek white cabinets and stainless steel appliances. A spacious island with a cooktop is surrounded by red metal stools. Natural light fills the area through a nearby window, complementing the contemporary design and providing a warm, inviting atmosphere.
Home in Boston
4.92 out of 5 average rating, 424 reviews

3 BR Private Family Home, S. Boston/Seaport/BCEC

A beautiful single home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features plenty of amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

Guest favorite
A vibrant exterior view of The Verb Hotel showcases a retro red bus alongside the building's large 'Verb' mural. Lush greenery surrounds the area, and Fenway Park's stadium lights are visible in the background, highlighting the connection to the iconic ballpark.
Hotel room in Boston
4.92 out of 5 average rating, 116 reviews

Steps from Fenway Park + Free Breakfast & Pool

Stay steps from Fenway Park in a hotel that lives and breathes rock ‘n’ roll. At The Verb, you’re not just checking into a room—you’re stepping into a retro-cool experience with a vinyl library, record players in every room, and a year-round outdoor pool. Whether you’re catching a game, exploring Boston’s iconic music scene, or sipping cocktails poolside, this stay is anything but ordinary. It’s fun, loud (in a good way), and full of personality—just like the city around it.

Top 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, 228 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

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, 174 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.

Popular amenities for Pleasure Bay vacation rentals

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