Family-friendly vacation rentals in Gloucester

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Gloucester family-friendly rentals

Family-friendly home rentals with a hot tub

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favorite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favorite
The kitchen features modern cabinetry and high-end stainless steel appliances, including a refrigerator and microwave. A dark countertop extends to a breakfast bar with two white stools. Warm hardwood floors and soft overhead lighting create an inviting cooking space.
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars3 days ago
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!
Guest favorite
Outdoor dining tables are set under large umbrellas, with guests enjoying a waterfront view. Sailboats are anchored in the calm water during sunset, creating a serene coastal atmosphere. The soft colors of the sky reflect on the water, enhancing the picturesque dining experience.
Guest suite in Kittery Point
4.95 out of 5 average rating, 294 reviews

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!

KyleRating, 5 stars4 days ago
This is one of the best Air B&B experiences that we’ve had…beautiful place and surroundings, great amenities and personal touches, wonderful recommendations. Couldn’t have had a better time.
Top guest favorite
The exterior of a fully remodeled three-bedroom house showcases a stylish design with multiple levels. A spacious rooftop deck is visible atop the structure, while an inviting front entrance leads into the well-maintained property. The surroundings include a paved driveway and landscaped areas.
Home in Newbury
4.98 out of 5 average rating, 51 reviews

Plum Island - Luxury Beach House

TracyRating, 5 stars9 months ago
We rent a house on PI every year and this house was perfect for us. We could walk to the basin with our SUP’s, easy walk to beach and stores and ice cream! We loved the double outdoor shower option for the kids after a long sandy day at the beach and they supplied all the beach toys, umbrellas and chairs! The rooftop deck was our favorite part we watched the sunset every night. We would rent this house again if the dates line up!
Superhost
An indoor pool area features clear waters with a section for relaxation, complemented by a whirlpool. Large windows allow natural light to fill the space, while the entrance door and pool steps are visible in the background.
Apartment in Hampton Beach
5 out of 5 average rating, 5 reviews

Condo with pool sleeps 4

ChristopherRating, 5 stars11 months ago
Great stay. Nice clean place. Good view of fireworks from the balcony.
A charming house is framed by colorful flowers and lush greenery, with steps leading up to the entrance. The exterior features a mix of stone and wood, complemented by red accents. Umbrellas provide shade over outdoor seating areas.
Home in Gloucester
4.9 out of 5 average rating, 10 reviews

Steps to Good Harbor Beach

MichaelRating, 5 stars71 months ago
Kate's house in Gloucester is an ideal place to experience one of the best beaches on the North Shore. Kate's home accommodated the eight of us very comfortably; the proximity to the beach was second to none and Kate and Michelle's response to a couple of minor issues we had was expeditious and friendly. There aren't enough superlatives I could use to recommend Kate's place.
The exterior of the property features a private driveway leading to a garage with a white door. A small entrance with a trellis supports potted plants, and natural light highlights the clean lines of the house, accentuating its welcoming facade.
Condo in Hampton Beach
4.69 out of 5 average rating, 89 reviews

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

RichardRating, 5 stars9 months ago
Our short stay was needed and this location was exactly what we was looking for! Very accommodating, private. Made us feel right at home. Our one complaint would just be the wifi. We struggled to get connected even with simple instructions. All in all, I would DEFINITELY reserve this location for our travels/vacations in the future! Thanks, Rick

Family- and pet-friendly home rentals

Superhost
The exterior of a spacious antique house is shown, featuring a yellow facade with green shutters. A large deck is visible in front, complemented by a white picket fence. The house is set against a clear blue sky, adding a bright and welcoming appearance.
Home in Lakeside Marblehead
4.76 out of 5 average rating, 168 reviews

Walk to Everything Great about Marblehead!

BillyRating, 5 stars3 weeks ago
Great stay, house perfectly as advertised, super cute and great for a big group. John was easy to reach and was able to accommodate an early check-in and a late check-out. Would come back again!
Top guest favorite
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 263 reviews

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

EmilyRating, 5 stars4 weeks ago
We loved staying here! Plenty of space for our family of 6, including one little one. It was exactly as pictured and well-stocked with spices in the kitchen and shampoo etc in the bathroom! Beds were super comfy and we loved how close it was to the lake, restaurants, and a playground. Would definitely stay here again!!
Top guest favorite
A wooden deck is situated in the foreground, featuring a small seating area and an umbrella. Lush greenery, including tall evergreen trees and colorful shrubs, creates a natural backdrop. A stone pathway leads into the garden area, enhancing the tranquil outdoor space.
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 194 reviews

Two bedroom Apt with a deck

CindieRating, 5 stars3 weeks ago
This was the cutest place! We all loved the garden space. The deck was very inviting. Rhona was kind enough to leave English muffins and butter for us. The selection of tea was fabulous! The bouquet and house plants made it feel very homey. There was an area close by that had a convenience store, a Dunkin Donuts, and a few decent restaurants. We would stay here again if we come back.
Top guest favorite
A two-story house with a light grey exterior is framed by a manicured lawn. Bright green accents are present on the front door, which is complemented by a small porch and steps. Surrounding shrubs and trees enhance the outdoor setting.
Home in Kittery
4.96 out of 5 average rating, 105 reviews

Spacious 2 BR Kittery Home - Walk to Portsmouth!

CathyRating, 5 stars3 weeks ago
We instantly felt at home! Everything we needed was there, including things that I often bring with me because they aren't usually provided. Erin has set up this house the way you would if you lived there yourself--extra pillows, blankets, bathroom and kitchen towels, kitchen and laundry detergent. Basic spices, coffee and tea, sugar and creamer, every kitchen gadget and utensil. Bath products, night lights, beach chairs and towels. Even a bluetooth speaker and use of their Netflix account! All we needed were a few groceries and some sunshine to enjoy the outdoor spaces and seasonal game room. The house is spacious and charming! Their check-in and check-out methods are easy and they left ample info on how things work in the house and local restaurant and activity recommendations. This is a great location and home. I almost wish we had brought the kids...
Guest favorite
A coastal view is captured, featuring distant houses and the ocean merging into the horizon. Power lines stretch across the scene, while lush green foliage adds a natural frame to the image. The clear sky complements the tranquil atmosphere.
Home in Ipswich
4.89 out of 5 average rating, 109 reviews

Hillside Ocean View 2BR with Private Beach Access

NancyRating, 5 stars1 week ago
Great location to getaway. Short walk to two different beaches as well as parking pass for great neck beach. Lots of room for two people to spread out. Lots of games to play. Living room was very comfortable, kitchen well stocked. Easy check-in and checkout
Guest favorite
An open concept living area features a modern kitchen with stainless steel appliances and white cabinetry. A dark sofa with decorative pillows faces a coffee table on a woven rug. The light blue walls add brightness to the space, while the 'SURF' lettering decorates the back wall.
Apartment in Salisbury
4.85 out of 5 average rating, 116 reviews

2BD Apt Steps to Beach|Pet Friendly| Wkly Discount

DanRating, 5 stars2 weeks ago
Amazing find! This is a perfect location. Salisbury is such a fun, cute, and affordable town. Lots to do and see and all super walkable from this house. You can get to beach in just a few steps. Take a walk down the beach to get some Beach Pizza at Cristy's (or Tripoli if you prefer) and enjoy one of the best arcades on the east coast at Joe's Playground. Host is super responsive and helpful. Beach gear being already there is a huge plus. Parking is easy. Love this place. Hope to be back some day.
Top guest favorite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Apartment in Concord
4.96 out of 5 average rating, 211 reviews

Mema's Place --Lovely apartment in private home

JackieRating, 5 stars3 weeks ago
Ellen is an excellent host and her apartment was spacious, clean and in a peaceful setting. We always enjoy staying at her place when we have the opportunity to be in the area.
Guest favorite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem
4.95 out of 5 average rating, 153 reviews

Quaint Little New Hampshire Lake House Getaway!

KevinRating, 5 stars2 weeks ago
We really enjiyed our stay and would recommend to anybody else.

Family-friendly home rentals with a pool

An aerial view captures the nearby beach and ocean, with soft waves lapping at the shore. The beach is dotted with sunbathers and umbrellas, while roads lined with buildings provide access. The highlighted location is positioned across from the beach, showcasing a prime coastal setting.
Condo in Hampton Beach
4.85 out of 5 average rating, 27 reviews

Slice of Paradise at Hampton Beach!!

JohnRating, 5 stars11 months ago
Second time staying at Micheal’s place and it’s always a great time. Will be back
Guest favorite
Cottage in Rye
4.91 out of 5 average rating, 78 reviews

Seaside Cottage in Rye NH

HeidiRating, 5 stars9 months ago
We love coming here. The beach is right across the street for me to look for rocks and sea glass and then right down the road is the beach for swimming. Perfect little getaway. Rachel is an amazing hostess.
Guest favorite
An indoor swimming pool is visible, featuring clear water and a hot tub adjacent to it. Large windows allow natural light to fill the space, and a door leads outside. Poolside access is provided by a metal ladder.
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars10 months ago
Clean and good storage for a small space. Good location
Superhost
A cozy kitchenette area is equipped with a microwave, coffee maker, and dining table with high-backed chairs. Decorative elements include a round red wall hanging and various kitchen utensils, creating a functional space. The layout opens to a sleeping area, with soft carpet underfoot.
Condo in Hampton Beach
4.89 out of 5 average rating, 18 reviews

100 yds/Hampton Beach Pool-4 guest

AndreaRating, 5 stars22 months ago
This was our first time at Hampton Beach and we couldn’t ask for a better host or place to stay. If felt like our home away from home. The location was perfect to everything and we didn’t need to use our car. The place was nice, clean and exactly as described and our host was so responsive and helpful! Thank you for making our first experience to the area a great one!!
An aerial view captures the coastline with sandy beach and ocean waves. Nearby buildings line the street, while the main structure is highlighted with a red arrow, indicating the listed suite's location. The openness of the area allows for ample sunshine.
Condo in Hampton Beach

Another Slice of Paradise

KatieRating, 5 stars11 months ago
Easy parking, clean, large balcony, view of the ocean and sunsets, lots of storage for clothes, easy quick communication with Michael. Ac units worked Amazing and very quiet. Tv in each room with a door for master bedroom privacy. Large public parking lot beside condo for family to park for the day. Quick mart with essentials and ice directly under rental. About 500 feet from condo to casino ballroom entrance. Great open clean space to make memories. Perfectly located between ocean, stores, shops and restaurants. Directly above busy street ( suggest ear plugs and eye mask if you are a light sleeper)
Guest favorite
An in-ground pool is surrounded by a grassy area, providing a refreshing outdoor space. Light blue lounge chairs are arranged nearby, offering places to relax. A white house with black shutters is visible in the background, framed by trees under a clear blue sky.
Home in Kittery
5 out of 5 average rating, 23 reviews

Summer Hill: Sweet New Englander on Maine Coast

ElizabethRating, 5 stars12 months ago
This was the perfect place for a girl's weekend. Very close to Kittery and Portsmouth shops, great seafood restaurants and State Park beaches. We were lucky the temperature was cool, as a lot of the windows didn't have screens and were too hard to open. I assumed maybe the owners haven’t fully switched over to summer mode as it's been cold up till recently. Wonderful decor, very whimsical.
Top guest favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 195 reviews

Country Cottage in the City

MariaRating, 5 stars2 weeks ago
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!
Superhost
An enclosed pool area features a clear water pool with a bubbling spa section. The pool is bordered by a smooth, tiled surface, and steps lead into the water. Large windows allow natural light to fill the space, and a door provides access to the exterior.
Apartment in Hampton Beach
4.74 out of 5 average rating, 122 reviews

Beautiful Beach Studio

AlexRating, 5 stars2 weeks ago
Good place to stay for Hampton Beach. Short walk to the water.

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

  • Total rentals

    380 properties

  • Total number of reviews

    13K reviews

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wifi availability

    380 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore