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!

Luxe Duplex nr Beach Seaport/Convention Cntr BCEC

NOTE: There is no on-site parking, however, there is free parking by the beach, just one block from the Airbnb A Stylish, newly built two-level home, all to yourself! Featuring three bedrooms, a full bathroom with a spacious walk-in shower, and thoughtful amenities throughout. Just steps from vibrant shops and restaurants, 1.5 miles from the Convention Center, and offering beach views, this home is ideal for large groups or business travelers seeking a relaxed, suburban feel right in the city.

Truly Oceanfront! Spacious Family Petfriendly Home

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

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

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.

Endless Summer Oceanside Views

Stay a weekend. Stay a week! All of the amenities of home are included in this spectacular apartment-on-the-water in the heart of Boston's North End. Enjoy amazing harbor views and cool ocean breezes in the light-filled stateroom. Prepare breakfast in the fully stocked chef's kitchen, complete with stainless steel appliances and a granite island. Invite friends over for drinks on the enormous deck. This is truly Boston's most unique and memorable vacation experience.

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.

Perfectly Renovated Home w/ Private Outdoor Oasis

COMPLETELY PRIVATE - NO SHARED SPACE OTHER THEN WASHER/DRYER AREA IN BASEMENT! Enjoy a private kitchen, 2 bedrooms, 2 baths and private outdoor space. The Master Bedroom has a king Bed with an ensuite bathroom. The Second Bedroom has a queen bed, gas fireplace and is right across from the second full bath. PARKING IS NOT INCLUDED. **outdoor furniture will be put away for the Winter in November & reassembled mid-May*

South Boston 3bdr BCEC & Seaport

Experience South Boston from our spacious, cozy apartment just a short walk from Broadway! Walk to cafes and boutiques, dine at our highly rated neighborhood restaurants, and explore nearby Seaport, BCEC (Convention Center), and our local beaches. Perfect for professionals, couples, small families, and anyone seeking a genuine neighborhood feel—just minutes from downtown Boston’s top attractions.

Curated Designer Retreat • Pool • Gym • Dining

Experience modern Everett living in this bright 2BR/2BA home! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit laundry, and spacious sunlit living areas. Relax by the courtyard pool, stay active in the 24/7 fitness center, or unwind in the outdoor lounges and fire pits. Close to Encore, Assembly Row and major highways for easy access to Greater Boston.