Holiday rentals in Castle Island

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.

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.

Bright Southie Retreat | Private Deck + Walkable

Enjoy a bright and spacious South Boston retreat with a private deck with outdoor lounge + TV. The condo features large bay windows, an open living area, fully equipped kitchen, workout equipment and dedicated workspace - ideal for both weekend getaways and longer stays. Located in the heart of Southie, you’ll be within walking distance of restaurants, coffee shops, bars, markets, and the waterfront. Public transit and quick Uber/Lyft rides make exploring the city simple and convenient.

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.

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.

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

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.

Guest Suite in Milton

This private suite features 2 comfortable bedrooms with cozy bedding. The suite includes a fully equipped kitchenette stocked with essentials for preparing meals. A clean, modern bathroom is supplied with fresh towels and basic toiletries for your convenience. It’s perfect for small families, couples, or business travelers. Enjoy complete privacy with your own separate entrance from the main house, allowing you to come and go as you please without disturbance.

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*

(Mlb7) Charming and Cozy Back Bay Studio

📍 Stay in the heart of Back Bay, just steps from Newbury Street, the Prudential Center, and Copley Square. This inviting space is close to Boston’s top hospitals—Mass General, Brigham and Women’s, Boston Children’s—prestigious universities like 🎓 Harvard, MIT, BU, and Northeastern, and iconic landmarks such as Boston Common, the Freedom Trail, and the Museum of Fine Arts.