Kid-friendly holiday rentals in Gloucester
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Gloucester
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in Gloucester
4.9 out of 5 average rating, 105 reviewsGloucester Beach House, near Good Harbor Beach!
15–22 Jan
Home in Rockport
4.97 out of 5 average rating, 282 reviewsCharming Toe-Hold, A Short Walk to Town and Beach
26 Jan – 2 Feb
Home in Gloucester
4.94 out of 5 average rating, 124 reviewsWonderful Rocky Neck home on Gloucester harbor
20–27 Apr
Home in Gloucester
4.96 out of 5 average rating, 121 reviewsBooking spring/summer-Overlooking Lobster Cove
6–13 Dec
Home in Gloucester
4.99 out of 5 average rating, 154 reviewsRocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
6–13 Dec
Home in Gloucester
4.82 out of 5 average rating, 161 reviewsGloucester Private Contemporary 4 bedrooms
14–21 Oct
Home in Gloucester
4.8 out of 5 average rating, 137 reviewsGloucester getaway ocean escape
6–13 Sept
Home in Marblehead
4.91 out of 5 average rating, 172 reviewsBungalow in Downtown Marblehead
20–27 Jan
Family-friendly apartment rentals
Flat in Gloucester
4.93 out of 5 average rating, 107 reviewsOpen Concept Eclectic Mod 3 BR
2–9 May
Flat in Beverly
4.94 out of 5 average rating, 617 reviewsBeverly Farms Apartment “Homeport”
18–25 Jan
Flat in Beverly
4.97 out of 5 average rating, 182 reviewsGarden City of the Northshore
10–17 Dec
Flat in Ipswich
4.98 out of 5 average rating, 121 reviewsCharming 2 Bedroom Apartment in Historic Ipswich.
6–13 Apr
Flat in Beverly
4.84 out of 5 average rating, 282 reviewsSalem/Beverly last minute opening for April!
18–25 Apr
Flat in Rockport
4.94 out of 5 average rating, 148 reviewsMary's By The Sea
24 Feb – 3 Mar
Flat in Rockport
4.87 out of 5 average rating, 163 reviews"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven
18–25 Nov
Flat in Gloucester
4.85 out of 5 average rating, 105 reviewsBright One Bedroom Apartment 5 Min Walk From Beach
19–26 Jul
Family-friendly apartment rentals
Apartment in Rockport
4.99 out of 5 average rating, 144 reviewsBearskin Neck Rockport ★ Amazing Views ★ Parking
17–24 Dec
Apartment in Rockport
4.99 out of 5 average rating, 186 reviews6 Tuna Wharf - Harbor right outside kitchen door!
24 Jun – 1 Jul
Apartment in Marblehead
4.99 out of 5 average rating, 151 reviewsHarbor Hideaway
7–14 Nov
Apartment in Marblehead
4.97 out of 5 average rating, 118 reviewsHistoric Studio|Minutes to Salem|Reserved Parking
23–30 Aug
Apartment in Hampton
4.84 out of 5 average rating, 172 reviews2 minutes walk to Beach parking and Wi-Fi
28 Oct – 4 Nov
Apartment in Beverly
4.95 out of 5 average rating, 211 reviews*Spacious2Br Retreat|DowntownBeverly|Salem&Parking
8–15 Nov
Apartment in Beverly
4.95 out of 5 average rating, 212 reviewsHistoric Chic|Downtown Gem|Cabot
22–29 Sept
Apartment in Hampton
4.87 out of 5 average rating, 103 reviewsLittle slice of paradise
18–25 Sept
Quick stats about holiday rentals that are kid-friendly in Gloucester
Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
£72 before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
- Martha's Vineyard Holiday rentals
- Cambridge Holiday rentals
- Portland Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Québec City Holiday rentals
- Québec Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals Cape Cod
- Family-friendly rentals New Hampshire
- Family-friendly rentals Massachusetts
- Beach house rentals Gloucester
- Beachfront rentals Gloucester
- Monthly Rentals Gloucester
- Rentals with outdoor seating Gloucester
- Pet-friendly rentals Gloucester
- Rentals with an EV charger Gloucester
- Rentals with breakfast Gloucester
- Private suite rentals Gloucester
- Apartment rentals Gloucester
- Rentals with a firepit Gloucester
- Cottage rentals Gloucester
- Rentals with a fireplace Gloucester
- Rentals with a washing machine and dryer Gloucester
- Waterfront rentals Gloucester
- Family-friendly rentals Gloucester
- House rentals Gloucester
- Rentals with a patio Gloucester
- Rentals with beach access Gloucester
- Flat rentals Gloucester
- Family-friendly rentals Essex County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom