Holiday rentals in Castle Island

Cozy 2-Bedroom in Heart of Southie

COMPLETELY PRIVATE IN-LAW SUITE! 2-bedroom/1-bathroom apartment with its own PRIVATE ENTRANCE, PRIVATE KITCHEN and PRIVATE LIVING ROOM! The only “shared” space is the washer/dryer room. We are 5 blocks from the beach, 1/2 block from Broadway (bars, restaurants, boutiques). We are a great way to see the city for much less than a hotel. Full kitchen, Charming fireplace, unique furniture, each room has central heat and AC! We do not provide parking. Local garage availability through SpotHero app.

Cozy & Modern Entire Residential Home ❤️

Discover your dream stay in this cozy 2bed, 1bath property located in picturesque Winthrop, Ma. It's perfectly situated 5-min from Yirrell Beach offering access to relaxation & city excitement. A convenient 20min drive from the bustling heart of Boston & 15min from Logan Airport & Encore Casino. Walking distance to public transportation & easy access to city adventures. clean & beautifully furnished and has a fully stocked eat-in kitchen, and a spacious deck. Short & long term stays are welcome

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!

Studio in East Boston #1

Peaceful and comfortable studio located in East Boston, Ma! It is located 10 mins away from the airport and 15 away from downtown Boston. It is also a 2 min walk from the train station. Guest will have full access to this studio which offers a bedroom, bathroom and kitchen area. Airport train station (10 mins), free shuttles to terminals. Kids under 3 years old don’t count as a guest. We offer a pack n play with a mattress! There is NO SMOKING inside the apt or hallways, fine will be charged.

2 BDR/2b- walk to Seaport & BCEC

We welcome you to stay at our stylish apartment in South Boston (Southie)! Located next to West Broadway, South Boston’s main road with plenty of restaurants, coffee shops, groceries, and boutique stores. Located walking distance to the Seaport District, Convention Center (BCEC), and our local Southie beaches. The space is ideal for travelling professionals, small families, couples, and those looking for a true neighborhood experience, tucked away just minutes from all the big city attractions.

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

South Boston. Minutes away from Convention Center

In the Heart of South Boston, walking distance to restaurants, coffee shops, bars and nightlife. Less then 1 mile from the convention center. 5 min in Taxi or Uber. #7 Bus from corner will drop you right outside Convention Center. 1 mile from children's museum accessible to downtown Boston via bus from the corner of our street. Bus will also take you to the Red line subway service which can access all subway MBTA lines. 1 block from the beach at pleasure bay and parks and Castleisland.

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

Ideal for families with young children, traveling professionals, campus visitors, and tourists! Spacious and recently renovated townhome in South Boston: 3 miles from Logan Airport, 3miles Fenway Park, 2 miles to Seaport, 1 mile to the Boston Convention Center, 1.6 miles to South Station (Commuter Rail/Amtrak), <1 mile to the Red Line (Broadway T-Station) to Kendall Sq (Harvard, MIT) and 1 block from the 9 Bus to Copley (~15min ride to Copley Sq). Great location for World Cup visitors!

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.

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.

Quiet 1BR retreat w/ private patio

Welcome to your private South Boston retreat on Telegraph Hill - a cozy apartment with a patio, full amenities, and an unbeatable location near the Red Line and Seaport District. - Sleeps 4 | 1 bedroom | 2 beds | 1 bath - Private patio w/ outdoor dining area & fully fenced backyard - Private entrance & self check-in w/ keypad - Full kitchen w/ GE gas stove, dishwasher & coffee setup - Free in-unit washer & dryer - long term stays welcome - Pet-friendly | Crib available on request

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