Family-friendly vacation rentals in Gloucester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Gloucester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gloucester family-friendly rentals
Family-friendly home rentals with a hot tub
Rental unit in Holliston
4.96 out of 5 average rating, 112 reviewsLake Link
Townhouse in Newton
4.8 out of 5 average rating, 218 reviewsAiry 3 BR House w/ Outdoor Hot Tub Sauna EV Charge
Rental unit in Roxbury
4.77 out of 5 average rating, 286 reviewsModern, Spacious 1BR for 4 - Easy Marathon Access!
Farm stay in Eliot
4.97 out of 5 average rating, 102 reviewsShilo Farmhouse: Goats & Hot Tub! Near Portsmouth
Guest suite in Kittery
4.9 out of 5 average rating, 755 reviewsSeacoast Oasis (NH & ME)
Rental unit in Hampton Beach
5 out of 5 average rating, 3 reviewsCondo with pool sleeps 4
Condo in Hampton Beach
4.67 out of 5 average rating, 79 reviews# 18 Large deluxe 3br, 2 1/2 bath condex sleeps 13
Home in Newton
4.75 out of 5 average rating, 53 reviewsBeautiful 6000 sq ft home 7 miles to Copley Sq.
Family- and pet-friendly home rentals
Rental unit in Ipswich
4.85 out of 5 average rating, 243 reviewsComfortable house, close to beach and downton IPSW
Home in Wakefield
4.96 out of 5 average rating, 219 reviewsWelcoming 7-room house <15 miles to Boston & Salem
Rental unit in Dorchester
4.93 out of 5 average rating, 102 reviewsBeautiful and Cozy Entire Apt in Boston
Rental unit in South End
4.96 out of 5 average rating, 335 reviewsCharming South End Duplex (Pets Ok)
Condo in East Boston
4.94 out of 5 average rating, 166 reviewsFamily Home + Near Downtown + Cool Backyard!
Townhouse in Wakefield
4.89 out of 5 average rating, 118 reviewsEntire 3 bedroom 1st floor home (pets by request)
Rental unit in Cambridge
4.86 out of 5 average rating, 415 reviewsCambridge Getaway @ Harvard & MIT
Cabin in Rockport
4.97 out of 5 average rating, 414 reviewsThe Solar Powered Dogtown Cabin at Applecart Farm
Family-friendly home rentals with a pool
Guesthouse in Hyde Park
4.95 out of 5 average rating, 178 reviewsCountry Cottage in the City
Guest suite in Beverly
4.85 out of 5 average rating, 681 reviewsHistoric North Shore, private suite & bathroom
Home in Manchester-by-the-Sea
4.75 out of 5 average rating, 4 reviewsCountry Estate, Heated Pool, near beach
Home in Seabrook Beach
4.9 out of 5 average rating, 42 reviewsFamily friendly beach house
Cottage in Rye
4.92 out of 5 average rating, 71 reviewsSeaside Cottage in Rye NH
Home in Kittery
5 out of 5 average rating, 22 reviewsSweet Traditional New Englander on Maine Coast
Condo in Hampton
4.78 out of 5 average rating, 50 reviewsBeachn' and North Beach
Home in Hull
4.95 out of 5 average rating, 22 reviewsSpacious 3-BR Furnished Beach Home
Quick stats about vacation rentals that are family-friendly in Gloucester
Total rentals
340 properties
Total number of reviews
10K reviews
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Wifi availability
330 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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