Family-friendly holiday rentals in Boston

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.

(N2F) Bay Windows, Newbury, Prime Location!

🌆 Stay on Iconic Newbury Street, Back Bay Experience Boston at its most stylish on Newbury Street, famous for its historic brownstones, tree-lined sidewalks, and vibrant atmosphere. 🛍️ Stroll right outside your door to explore designer boutiques, local shops, art galleries, and some of the city’s best cafés and restaurants. You’ll be just steps from Copley Square, the Prudential Center, and the Charles River Esplanade, with easy access to the Green Line T for exploring the rest of the city.

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Charming, spacious gem in heart of City

Amazing location with this 1st floor airy and serene, fully furnished apartment in a two family, historic, recently renovated Greek Revival row-house with a private entrance. Located in a quiet, family-friendly location close to the Charles River, Kendall Square, Cambrideside Mall, Kendall Theater, Harvard Square, MIT, groceries, cafes, restaurants and more. Close to red line (Kendall), green line (Lechmere) and multiple convenient bus lines as well as a quick drive from Logan Airport.

SouthEnd Penthouse

Centrally located penthouse unit in the heart of Boston SouthEnd. Abundance of sunlight, spacious living area, and open kitchen will make your stay a unique and charming experience in a historically preserved area. Ideal to explore the local neighborhood restaurants or walk to Boston commons, the ballpark, downtown or Newbury Street. The neighborhood is historic to Boston with classical brick stone look and the place itself is quite a gem, very quiet and open dining+living room style.

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

Second Oldest Home in Beacon Hill

Small private studio apartment built in 1789, located at the top of Beacon Hill. It is next door to the oldest house in Beacon Hill and is close to many tourist attractions while still being in a quiet local neighborhood. You will be with in 5 minutes of the Massachusetts State House and the oldest park in the country known as the Boston Common. You will also be within walking distance of Back Bay and the North End. We welcome you to our small home in Beacon Hill.

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

Harvard Square Home in Heart of Cambridge!

Harvard Square apartment with treetop views. Come visit the heart of Cambridge in this quiet, bright unit with a mix of modern and period pieces. Harvard campus and libraries, restaurants, shops, public transportation all minutes away. 3 Day visitor Parking pass available for surrounding streets. We continuously strive to create an eco-friendly environment by using products that are biodegradable. Relax in this peaceful apartment. Your yoga mat awaits.

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Peaceful Garden Apartment

Your beautiful garden guest unit is a tranquil getaway. The layout is ideal - a bedroom with an ensuite bath; living room with a pull out couch and a door that transforms the living room into a private bedroom; a second full bath; and a kitchen/dining area. Best of all, it's less than a ten minute walk to 500 acres of parkland and "JP" center with great restaurants, pubs, bakeries and shops.