Family-friendly holiday rentals in Watertown

4.78 out of 5 average rating, 181 reviews

A welcoming entrance is framed by neatly trimmed shrubs and seasonal planters, featuring vibrant flowers and a pumpkin. The stairs lead to a door with a yellow hue, flanked by windows with green shutters, set against the backdrop of a quiet neighborhood.

Apartment in Belmont

Quiet, convenient and cozy!

Clean and comfortable. 2 bedrooms, full bath and kitchen, and free parking spot. 1st floor of 2-family. Owner lives upstairs. Door to the guest's residence is through a rear hallway. Hallway is occasionally shared with owner. 1 block to 15 min bus ride to Harvard Sq. (directions below) Easy access to Boston but in green and quiet neighborhood. There's no living room but there is comfortable sitting area in one of the bedrooms. Work space can also be arranged. Please let us know what you need.

FamilyKitchenCondition

4.93 out of 5 average rating, 105 reviews

A contemporary living area is showcased with a large flat-screen TV positioned on a wooden console. A cozy armchair and a plush area rug complement the warm hardwood flooring, while a framed artwork decorates the wall above. A decorative item is displayed on the console.

Apartment in Belmont

Modern Cozy 2 Bed Near Cambridge

Brand new, stylish Airbnb in Cushing Square, Belmont! If you're planning a trip to Boston and seeking a clean, contemporary Airbnb, this is the ideal spot for you. Located in the heart of the recently developed Cushing Village, right across from cafes, restaurants & shops. Mass Pike- 2 miles Watertown Square- 1 mile Star Market - 1 mile Mount Auburn Hospital- 2 miles St. Elizabeth's Hospital- 2.5 miles Harvard- 3 miles MIT- 4 miles Boston Common- 7 miles Close to Route 95, Route 93, & Route 2

Indoor spacesFamilyAmenities

4.97 out of 5 average rating, 156 reviews

A well-lit bedroom features a spacious bed covered in a warm yellow quilt. Two teal cushions and a decorative pillow add a pop of color. Light streams in through two window frames with wooden blinds, creating a bright and inviting atmosphere.

Guest suite in Watertown

Charming 2nd floor Suite w/ a Separate Entrance

Welcome to our retro-inspired one-bedroom apartment/suite with a separate entrance on the second floor of our two-family home. The space is newly renovated and includes all new linens, a rug, pillows, and a comfortable bed. It's perfect for those who want a homier feel than a hotel but don't need access to a kitchen. The suite includes an electric kettle and a mini-fridge, but no microwave or TV. Please note there is a flight of stairs to access the unit. Come enjoy a stay in our neighborhood.

Indoor spacesKitchenHeating

4.92 out of 5 average rating, 274 reviews

A cozy bedroom features a fold-down sofabed dressed in red linens, complemented by a fluffy pillow. Warm light from wall sconces casts a soft glow over the space. A decorative area rug with a world map adds character, while a bookshelf offers storage and décor.

Guest suite in Watertown

sofa-bed w 3” foam pad, b’room, bath & work space

A 3rd-floor bedroom has a fold-down sofabed with a futon mattress, 3” foam pad, flannel sheets now, draperied windows facing north, closet spaces, small writing desk and dresser. Private rear-door coded entrance. Complete bathroom w shower, mini-fridge, microwave oven and work space. Free wi-fi. Free on-street summer parking; from January 1 an overnight winter parking ban is in place til March 1. If you have a car we’ll provide a space for you. A new ductless mini-split provides AC /heat

FamilyIndoor spacesWi-Fi

4.93 out of 5 average rating, 162 reviews

A spacious living area features two gray sofas with yellow accent pillows, arranged around a circular wooden coffee table. A gas fireplace is centered against a white mantel, complemented by large windows allowing natural light and views of greenery.

Townhouse in Waltham

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. Just 1 min walk to Waltham Rail Station (some ambient rail sounds possible), buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

FamilyIndoor spacesRiver

4.99 out of 5 average rating, 141 reviews

A modern kitchen with sleek cabinetry and a spacious island features three high-backed bar stools. Stainless steel appliances are visible, along with a contemporary backsplash. Natural light brightens the space through large windows, offering views of the green meadow outside.

Apartment in Brighton

New 3 bedroom, 2 bath unit, meadow view!

Located on the 2nd floor of a brand-new building, this modern unit is perfect for family and group trips! Living in this quiet, residential neighborhood, you will be minutes away from many universities (BC, BU, Harvard, MIT, NEU, etc.), downtown Boston, and many major attractions (Boston Common, Newbury Street, Freedom Trail, etc.). Relax and enjoy the peaceful meadow views at the back of the building. Subway stations, bus stops, and restaurants and grocery store are within walking distance!

Indoor spacesKitchenAccess

4.94 out of 5 average rating, 592 reviews

Apartment in Cambridge

Spacious Strawberry Hill Suite (West Cambridge)

This 3rd floor suite is less than 2 miles west of Harvard Sq. You'll have exclusive access to the space, which has a full bathroom and kitchenette. There is a queen bed suitable for two people and the couch in the living room converts to a bed for one. Our neighborhood is friendly, safe, and has a lot to offer. Public transportation (bus) is a 5 minute walk. The trip to Harvard Square is 10-15 minutes. I live in the home downstairs and am available should you need me during your stay.

KitchenIndoor spacesLayout

4.83 out of 5 average rating, 150 reviews

A spacious bedroom features two neatly made beds, one larger and one smaller, adorned with white bedding. A bedside table holds a lamp, and a window with light curtains allows natural light to enter, complemented by warm LED ceiling lights.

Condo in Waltham

Lovely one bedroom apartment condo, with parking

The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

KitchenIndoor spacesHospitality

4.99 out of 5 average rating, 117 reviews

A stylish living room features a green sectional sofa complemented by colorful throw pillows. A round coffee table rests on a patterned area rug. Art pieces adorn the walls, and natural light enters through windows, illuminating the warm wooden flooring and brick fireplace.

Home in Arlington

The Brickhouz at Arlington !

Just a little bit of everything for everyone to have a spectacular time in Boston, perfect for family gathering ! A funky and quirky cozy 4-bedroom brickhouse smack right in the middle of Arlington Center. 10 mins to Harvard Square, 15 minutes to Boston and Logan airport. Sleeps 8 - 2 bathrooms. Short 1 minute walk to cafes and restaurants. Discounts available for longer stays. Strictly no parties or unapproved pets.

FamilyIndoor spacesCleanliness

4.95 out of 5 average rating, 472 reviews

Apartment in Newton

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

Indoor spacesKitchenNearby

4.94 out of 5 average rating, 112 reviews

A light-filled living room is presented with large windows offering views of the surrounding neighborhood. A navy blue sofa is paired with a yellow accent chair, and a wooden coffee table is centered on a patterned rug. A tall bookshelf holds various books and decorative items.

Townhouse in Arlington

Modern 2-Story Near Boston & Harvard

Large, stylish, two-floor home in East Arlington, minutes from Cambridge and Boston. Set on a quiet street near Mass Ave, with easy access to Harvard University, MIT, and Tufts University. Public transit via Red Line and 77 bus, plus convenient access to Gillette Stadium. Spacious, quiet, and perfect for families or groups seeking comfort near the city.

KitchenFamilyAmenities

4.94 out of 5 average rating, 254 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

The guesthouse is located on a lovely quiet street, less than 1 mile to I-90 and just minutes to Boston. Enjoy a kitchen, dining, living space, bedroom, 2 baths, solarium & deck with table & chairs. Space includes 2 twin beds & queen sleep-sofa.

Indoor spacesFamilyComfort

Popular amenities for Watertown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 218 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

FamilyIndoor spacesAmenities

4.92 out of 5 average rating, 236 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 282 reviews

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

KitchenIndoor spacesWi-Fi

4.78 out of 5 average rating, 359 reviews

The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.

Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

KitchenIndoor spacesHeating

4.94 out of 5 average rating, 36 reviews

A modern bathroom features double vanities with stylish circular mirrors and a glass shelf above. Natural light floods in from the window, highlighting the neutral tile floor and sleek cabinetry. A contemporary toilet is positioned nearby, promoting a clean and functional space.

Guest suite in Waltham

Cozy & convenient place with sunset & garden view

KitchenComfortLocation

5.0 out of 5 average rating, 32 reviews

Home in Wellesley

Wellesley Spacious and Modern

FamilyKitchenHeating

4.95 out of 5 average rating, 91 reviews

An open-concept living space is highlighted by warm wood flooring and soft lighting. A modern kitchen with wooden cabinets and sleek countertops is visible in the background. Comfortable seating is arranged around a glass coffee table, inviting relaxation and conversation.

Home in Newton

Explore Boston in style! Dream home (STR-26-3)

KitchenIndoor spacesAccess

4.95 out of 5 average rating, 20 reviews

Apartment in Somerville

New luxury 4BR/3 bath apartment with AC & EV charger

KitchenFamilyCheck-in

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 234 reviews

The spacious living area features warm wooden flooring and a central table with seating. Natural light enters through a nearby door, complemented by modern pendant lighting. A kitchenette is visible with a stylish shelf displaying decorative items, creating a functional yet inviting environment.

Apartment in Arlington

Dixie’s House, 1BD in Arlington

KitchenIndoor spacesHeating

4.92 out of 5 average rating, 414 reviews

A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.

Apartment in Newton

Conveniently Located Private Garden Apartment

Indoor spacesFamilyNearby

4.89 out of 5 average rating, 169 reviews

A charming two-story yellow house is framed by lush green shrubs and trees. The front porch features a covered entrance with a set of steps leading up to double doors. Large windows are visible on the upper floors, enhancing the light and airy appearance.

Apartment in Cambridge

Urban oasis in Huron Village

KitchenIndoor spacesParking

5.0 out of 5 average rating, 209 reviews

A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.

Guest suite in Weston

Flower Farm Getaway 2BR, 20 Min To Boston

FamilyIndoor spacesAir conditioning

4.85 out of 5 average rating, 123 reviews

Apartment in Waltham

2bed/2bath Apt at Waltham Landing. Middle Unit

Indoor spacesFamilyLaundry

4.98 out of 5 average rating, 121 reviews

A living area features a comfortable sofa with cushions, a glass coffee table, and a flat-screen TV on a stand. A round dining table with wooden stools is visible, along with a large mirror reflecting the space. Sunlight enters through sheer curtains.

Apartment in Waltham

Just Renovated, Private & Quiet 2 Bedroom Condo

KitchenFamilyOutdoor spaces

Apartment in Chestnut Hill

ThouArtHome, BC, DanaFarber, Parking, PetFriendly.

FamilyKitchenComfort

4.76 out of 5 average rating, 243 reviews

4.94 out of 5 average rating, 110 reviews

The exterior of a Victorian-era home is surrounded by lush greenery, with vibrant flowers lining the pathway. A spacious porch is visible, framed by tall trees, inviting guests to enjoy the natural setting. A gravel driveway leads to the welcoming entrance.

Home in Waltham

Harvard House-The Gathering Place.

KitchenFamilyBathroom

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 445 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

Indoor spacesKitchenValue

4.96 out of 5 average rating, 159 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

KitchenFamilyAccuracy

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

Country Cottage in the City

Indoor spacesFamilyCondition

4.95 out of 5 average rating, 217 reviews

4.88 out of 5 average rating, 206 reviews

A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.

Guest suite in Revere

Amazing studio

KitchenIndoor spacesGetting around

4.92 out of 5 average rating, 126 reviews

Apartment in Everett

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

KitchenFamilyCheck-in

4.99 out of 5 average rating, 167 reviews

Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

FamilyKitchenLong stay

4.97 out of 5 average rating, 120 reviews

The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.

Home in Weston

Spacious vacation unit in premium suburban town

Indoor spacesFamilyBackyard