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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.

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Rental unit in Rockport

4.73 out of 5 average rating, 105 reviews

Charming Apt in Ctr of Rockport-Walk to Beach-WiFi

Immerse yourself in the heart of America's most famous seaside artists' colony. Located on Bearskin Neck and nestled in the center of Rockport's vibrant and exciting colonial historic district, replete with shops, galleries, restaurants, fishmongers, kayaking, schooner tours, and the finest lobsters in the North Atlantic. Steps from our door you may visit idyllic beaches, bandstands, our library, churches, yacht clubs, whale watching tours, fishing charters, art association, golf, & bicycling.

Home in Salisbury

4.9 out of 5 average rating, 126 reviews

NEW 3BR home, incredible views - Beach across St

Enjoy sunrises and sunsets with an expanse of windows that offer breathtaking views of the river and marsh in a new construction, BEAUTIFUL, single family home. Over 2000 Sq Ft wTile & hardwood floors. 1st level has Open living room/kitchen, half bath & 1 bedroom. 2nd Floor has 2 bedrooms, bath, laundry & Large outdoor deck. Beach is a 2 minute walk across the street. 10 minutes to Browns Seafood restaurant, Ice Cream, Groceries & more. 2+ Parking spots. We follow the Advanced Clean Protocol.

Rental unit in Winthrop

4.96 out of 5 average rating, 295 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Condo in Portsmouth

4.94 out of 5 average rating, 710 reviews

Downtown Gem |Group Getaway A+ Locale Free Parking

AMAZING LOCATION This downtown gem has 2 floors (1200sf) of living space, steps away from restaurants, theater, jazz club, bars, music hall, shopping + waterfront concerts. Luxe linens + modern décor. Full kitchen, 3 bedrooms, 1.25 baths, central air + hardwood floors. Private yard + 2 FREE parking spots. MUST be 24+ to reserve. Parents+kids < 24 is permitted. No 3rd party bookings. If you book, you must be staying. NO PETS. MOBILITY issues?? PLEASE take note of STEEP+NARROW staircase. Sleeps 8.

Home in Hampton

4.9 out of 5 average rating, 127 reviews

Luxury Vacation House at North Beach

Beautiful family house located in a quiet residential neighborhood, just steps from North Beach comes with everything you need for a relaxing vacation! This 4BR, 4.5BA house with two living areas, spacious kitchen, & ocean views is the perfect location for a luxury getaway. Three bedrooms have queen beds, & 1 has 2 full beds. With two outdoor living spaces to enjoy the summer weather, this house also has a washer/dryer and wi-fi, dining table for 8, and 4 additional seats at the kitchen island.

Home in Wayland

4.77 out of 5 average rating, 460 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Condo in Cambridge

4.89 out of 5 average rating, 135 reviews

#1A-Cambridge Harvard MIT with In unit W/D!

WALK to Harvard, MIT and steps to all public trans & blue bikes! Gorgeous fully furnished (1 month minimum). stays! Great for visiting nurses, Harvard, MIT fellows! In-unit washer/dryer and full eat in kitchen with granite counters, dishwasher/disposal (all cooking utensils, etc.). Light filled living room with custom built in bookshelves, large bay windows, and great picture book collection... All wood floors. AC/WIFI/all utilities included! Pets (yes large dogs too) welcome approval only.

Home in Hampton Beach

4.94 out of 5 average rating, 105 reviews

Pearls on Perkins, Beautiful Condo!

The Pink Pearl is the downstairs 1100 sqft. condo unit! With 2 bedrooms (1 queen & 1 twin bedroom, includes sheets, blanket & comforter), 2 full baths, with towels for your convenience, there is also a comfortable pull out sleep sofa, TV, WIFI, central air, washer/dryer. A large front to back fully equipped kitchen/living room with pots, pans & dishes for home cooked meals. Large roof top deck to watch the sunset over the Hampton River. Fantastic location, only 1 street from the beach.

Rental unit in Beverly

4.75 out of 5 average rating, 293 reviews

Salem/Beverly/ North Shore- "Sea" Us This Season!

Bringing the gang to Boston's North Shore? Holiday visitors? You'll love this unfussy, spacious, apartment in historic Beverly. Plenty of room for the family! College visits, holidays & more. 1st floor with plenty of kitchen space. Explore the area from this central location on a quiet side street with parking. Walk to beaches, entertainment and a vibrant downtown with a great food scene. Just steps from the commuter rail with trains to Boston, Salem or points north! Let's book!

Guest suite in Kittery Point

4.95 out of 5 average rating, 265 reviews

Enjoy Warm Autumn Days; Cool Hot Tub Nights!

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

Home in North Andover

4.95 out of 5 average rating, 149 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Rental unit in West Newton

4.83 out of 5 average rating, 380 reviews

Airy, Sunny, CLEAN 2 BR in Waltham- 15 min BOS

CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College.

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Popular amenities for Gloucester family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in West Roxbury

4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Cottage in Newbury

4.67 out of 5 average rating, 3 reviews

Ocean Front house on Plum Island

Condo in Hampton Beach

4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

Home in Gloucester

4.9 out of 5 average rating, 10 reviews

Steps to GOOD HARBOR BEACH!

Guest suite in Kittery

4.9 out of 5 average rating, 814 reviews

Seacoast "Hot Tub" Oasis (NH & ME)

Condo in Hampton Beach

4.69 out of 5 average rating, 89 reviews

# 18 Large deluxe 3br, 2 1/2 bath condex sleeps 13

Guest suite in Canton

4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

Place to stay in Hampstead

4.88 out of 5 average rating, 89 reviews

Sunrise Sunset Lakefront Suite

Family- and pet-friendly home rentals

Home in Wakefield

4.96 out of 5 average rating, 239 reviews

Welcoming 7-room house <15 miles to Boston & Salem

Cabin in Rockport

4.97 out of 5 average rating, 429 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Rental unit in South End

4.96 out of 5 average rating, 357 reviews

Charming South End Duplex (Pets Ok)

Home in Salem

4.94 out of 5 average rating, 143 reviews

Quaint Little New Hampshire Lake House Getaway!

Rental unit in Hampton

4.96 out of 5 average rating, 157 reviews

Cozy 1 Bedroom Apartment with private entrance!

Home in Medford

4.83 out of 5 average rating, 131 reviews

Sunny home minutes from Boston. Free parking.

Rental unit in Cambridge

4.87 out of 5 average rating, 432 reviews

Cambridge Getaway @ Harvard & MIT

Rental unit in Ipswich

4.85 out of 5 average rating, 269 reviews

Comfortable house, close to beach and downton IPSW

Family-friendly home rentals with a pool

Condo in Hampton Beach

4.85 out of 5 average rating, 27 reviews

Slice of Paradise at Hampton Beach!!

Cottage in Rye

4.91 out of 5 average rating, 78 reviews

Seaside Cottage in Rye NH

Condo in Hampton Beach

4.89 out of 5 average rating, 18 reviews

100 yds/Hampton Beach Pool-4 guest

Home in Kittery

5 out of 5 average rating, 23 reviews

Summer Hill: Sweet New Englander on Maine Coast

Guesthouse in West Roxbury

4.95 out of 5 average rating, 191 reviews

Country Cottage in the City

Rental unit in Hampton Beach

4.74 out of 5 average rating, 121 reviews

Beautiful Beach Studio

Home in Hull

4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

Home in Derry

4.83 out of 5 average rating, 134 reviews

Beautiful Lakefront Vacation

Quick stats about vacation rentals that are family-friendly in Gloucester

Total rentals
370 properties
Total number of reviews
12K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Wifi availability
370 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore