
Holiday rentals in Castle Island
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Castle Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

2BR Spacious Yacht - Heat & AC- On Freedom Trail
Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

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.

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.

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.

Luxurious Open-Concept Home with Roof Skyline View
Enjoy a luxurious stay at this centrally located home, just minutes from the airport, downtown, and Encore Casino. Featuring an open-concept design with high ceilings and stunning views of Everett’s city skyline, this home is perfect for both relaxation and adventure. • Prime Location: Close to key attractions and entertainment. • Modern Comforts: Rooftop deck, Spacious, stylish, and equipped with everything you need.
Popular amenities for Castle Island holiday rentals
Other great holiday rentals in Castle Island

Luxe Duplex nr Beach Seaport/Convention Cntr BCEC

Guest Suite in Milton

4 Bedrooms, 5 Beds, 2.5Bath Near Downtown Boston

Charlestown apartment with private patio

Stay in the Heart of Fenway & Berklee

Luxurious Fenway 2BR Penthouse w/ Roof Deck

Southie condo with Hot tub

North Scituate Cottage
Destinations to explore
- New York City Holiday rentals
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- Philadelphia Holiday rentals
- Boston Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Boston Common
- Boston Seaport
- Gillette Stadium
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- MIT Museum
- East Sandwich Beach
- Duxbury Beach
- North Hampton Beach
- Crane Beach
- Boston College
- Northeastern University
- Quincy Market
- Tufts University





