Vacation rentals in Pleasure Bay

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!

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.

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.

Nana's House

Your family will be close to everything when you stay at this centrally-located home. 2 mins away from the beach and a few doors away from a bus to bring you to downtown Boston/Seaport, freedom trail, museums, shopping and entertainment. You will be surrounded by the history and beauty of a family friendly neighborhood. Just a 5 min. walk to Broadway with shops, restaurants and bars for almost 2 miles. Spacious shared backyard. Family lives on premises in other unit if you need anything.

Timeless Stay | Freedom Trail. Fitness Center

Explore a beautifully reimagined luxury hotel, The Newbury Boston, where the bustle of the Back Bay is your playground and the idyllic Boston Public Garden your front yard. Attractions just nearby: ✔Boston Expressionist paintings and Chinese ceramics at Museum of Fine Arts ✔Deep dive into history at Boston’s Tea Party Museum ✔Sharks, rays, penguins at New England Aquarium ✔400 years of Boston’s history and the story of nation’s pursuit of liberty, Freedom Trail ✔Downtown Boston

Paul Revere Suite PVT Entry/BATH QN Bed History

*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.

Beautiful Southie Single Family

Your whole family can enjoy this single-family rental in the heart of Southie. Five bedrooms with lots of room for families of all ages! This house is situated in a picture-perfect, calm, and quiet part of Boston but is centrally located a short walk from beaches, parks, shopping, and top-rated restaurants. Easy public transit connects you directly to the Back Bay, Seaport, or Downtown. Plus you can bring your car and park in our garage spot a 10 min walk from the front door.

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

Seaport Hotel® Boston, Deluxe room king bed

Deluxe room one king bed features a king bed with a pillowtop mattress, local artwork, and city or Boston Harbor views. Enjoy a 55-inch HDTV, complimentary wifi, Keurig coffee maker, mini refrigerator, laptop-sized safe, and a beautifully appointed bathroom with Gilchrist and Soames BeeKind toiletries, fog free mirror, and walk-in shower or tub. Additional amenities include complimentary bottled water, rolling desk, Tivoli audio system, and access to the Wall Street Journal.

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

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.

In The Heart of Boston’s Seaport + Rooftop Bar

The Envoy Hotel connects Boston with food, drink, and skyline views that define the city. At Para Maria, Chopped champion Tatiana Rosana serves eclectic dishes inspired by French training, Cuban roots, her wife’s Korean heritage, and New England grit. Rooftop at The Envoy offers craft cocktails and fire pits with stunning harbor views. With art‑filled spaces, vibrant design, and Seaport originality, The Envoy delivers hospitality that rises above the ordinary.