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

4.83 out of 5 average rating, 160 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).

Superhost

Private room in Boston

4.86 out of 5 average rating, 627 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.

Superhost

Apartment in Boston

5 out of 5 average rating, 94 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!

Superhost

Private room in Winthrop

4.97 out of 5 average rating, 405 reviews

Sky harbor wine lounge experience Plane Watching

Treat yourself to a getaway at my newly renovated nautical themed home nestled in Winthrop’s charming friendly seaside neighborhood close to Logan Airport and downtown Boston. We are delighted to offer you a spacious private bedroom with full bed, refrigerator & AC. You’ll share my home with me (Shirley) my two cats, Caleb & Otto and one other airbnb guest room. For an additional $40 you have access to the Sky Lounge overlooking Boston harbor. You would share the rest of my home with us.

Superhost

Guest suite in Boston

4.96 out of 5 average rating, 425 reviews

Paul Revere Suite PVT Entry/BATH QN Bed Sparkling

*5 STAR ★★★★★ **No Chores! No To-Do List!** Yes, Private Bathroom! Cleaned and Sanitized *Luxury and Comfort *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *National Historic Sites *Dedicated Luxury Suites *Key-less Coded Access *Queen Pillow Top Bed *Private bath with shower *Great Bath Amenities *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking.

Superhost

Guest suite in Winthrop

4.95 out of 5 average rating, 964 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.

Superhost

Private room in Boston

4.96 out of 5 average rating, 438 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

Superhost

Apartment in Boston

4.88 out of 5 average rating, 152 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.

Superhost

Private room in Boston

4.98 out of 5 average rating, 289 reviews

Southie Gem: Private Room & Bath Near Seaport

Charming shared condo in the heart of “Southie,” one of Boston’s most beloved neighborhoods. Just a short walk to the Seaport, public transit, beaches, and a vibrant mix of bars, restaurants, and shops. Enjoy easy access to all parts of the city! Perfect for couples, solo travelers, and business guests. You'll have a private bedroom and bathroom in a shared unit. On-site parking may be available upon request in advance. Daily parking rate: $30.

Superhost

Private room in Boston

4.97 out of 5 average rating, 242 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.

Superhost

Private room in Boston

4.85 out of 5 average rating, 226 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.

Superhost

Private room in Boston

4.87 out of 5 average rating, 836 reviews

Spacious, Modern & Comfy East Boston Hidden Gem

Welcome to Boston! This bright, modern private room is perfect for solo travelers or couples. Located in East Boston, you’re just 5 minutes from Logan Airport and 2 subway stops to Downtown, the North End, Seaport, and more. Enjoy a comfy bed, fast Wi-Fi, and a secure room with key access. Thoughtfully designed shared spaces include a fully equipped kitchen. Walk to parks and cafes, a. We look forward to hosting you!