Family-friendly holiday 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.
Holiday 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
Guest suite in Kittery Point
4.94 out of 5 average rating, 237 reviewsCoastal Views! Walk to Wharf & Enjoy Hot Tub Too!
Home in North Andover
4.94 out of 5 average rating, 131 reviewsNana-tucket Inn
Apartment in Boston
4.77 out of 5 average rating, 283 reviewsModern, Spacious 1BR for 4 - Easy Marathon Access!
Townhouse in Newton
4.8 out of 5 average rating, 218 reviewsAiry 3 BR House w/ Outdoor Sauna Hot Tub EV Charge
Condo in Hampton
4.69 out of 5 average rating, 77 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.
Condo in Hampton
4.93 out of 5 average rating, 28 reviewsHampton 100 yards to beach
Home in Salisbury
4.83 out of 5 average rating, 104 reviewsNamaste at the Beach
Family- and pet-friendly home rentals
Apartment in Ipswich
4.85 out of 5 average rating, 238 reviewsComfortable house, close to beach and downton IPSW
Apartment in Ipswich
4.89 out of 5 average rating, 240 reviewsIpswich Apartment
Apartment in Newbury
4.92 out of 5 average rating, 124 reviewsPretty Cottage on Plum Island, Newbury MA
Barn in Carlisle
4.83 out of 5 average rating, 524 reviews✨Entire Secluded Barn Suite Ctr Historic Carlisle✨
Tiny home in Kittery
4.95 out of 5 average rating, 440 reviewswater view property "The Little House"
Apartment in Natick
4.98 out of 5 average rating, 334 reviewsScandi-Modern Apartment
Guest suite in Salem
4.83 out of 5 average rating, 599 reviewsSalem House
Apartment in Portsmouth
4.94 out of 5 average rating, 477 reviewsPrivate Sunny Apartment in hip Portsmouth West End
Family-friendly home rentals with a pool
Guesthouse in Dedham
4.95 out of 5 average rating, 175 reviewsCountry Cottage in the City
Apartment in Winthrop
4.96 out of 5 average rating, 281 reviewsCody's Place Boston Airport Pool/Beaches ParkFree
Villa in Cambridge
4.99 out of 5 average rating, 194 reviewsPhil's Harvard & MIT Home
Home in Seabrook
4.9 out of 5 average rating, 42 reviewsFamily friendly beach house
Apartment in Hampton
4.72 out of 5 average rating, 113 reviewsBeautiful Beach Studio
Home in Manchester-by-the-Sea
4.75 out of 5 average rating, 4 reviewsCountry Estate, Heated Pool, near beach
Condo in Hampton
4.78 out of 5 average rating, 50 reviewsBeachn' and North Beach
Cottage in Rye
4.92 out of 5 average rating, 71 reviewsSeaside Cottage in Rye NH
Quick stats about holiday rentals that are family-friendly in Gloucester
Total rentals
340 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
330 properties include access to Wi-Fi
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Total number of reviews
10K reviews
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