Family-friendly vacation rentals in Westbrook

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Westbrook

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.
Loft in Falmouth
4.95 out of 5 average rating, 689 reviews

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Top guest favorite
Tiny home in Gorham
4.97 out of 5 average rating, 115 reviews

The Chickadee Tiny House

The newly built Chickadee allows you to experience upscale tiny living within a stones throw of some popular local attractions. While we feel the Chickadee offers plenty of privacy from the inside you should make note that it is located in the middle of a neighborhood setting and the landscaping is still being worked on though won't be disruptive to your stay. Just under a mile from downtown Gorham 20 minutes to Portland Ski, swim, shop, eat, leaf peep, hike, the activities nearby are endless

Top guest favorite
Home in Westbrook
4.89 out of 5 average rating, 617 reviews

Cozy Maine Cottage • Near Jetport & Coast

Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

Superhost
A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.
Loft in Portland
4.89 out of 5 average rating, 360 reviews

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Guest favorite
A spacious living area features a sectional sofa in soft brown upholstery, accented with decorative pillows. A black coffee table displays a decorative centerpiece, while a floor lamp adds light. The room is complemented by light grey walls and modern decor.
Guesthouse in Westbrook
4.83 out of 5 average rating, 118 reviews

Modern stay Westbrook Maine

Welcome to our modern 1-bedroom basement retreat, nestled in the charming town of Westbrook, just a short 3-minute drive from the Portland, Maine. With its stylish design and upscale amenities, this Airbnb offers the perfect blend of comfort and convenience for your stay in the area. The bedroom features a Queen-size bed, a queen-size pull-out sofa in the living area, accommodating additional guests comfortably in the spacious living area. There’s a $200 pet fee per pet.

Top guest favorite
The interior of the yurt is divided into two distinct areas. One side features a spacious bed with light bedding, while the other side includes a cozy loveseat and a small coffee table. An area rug adds warmth to the flooring, enhancing the inviting space.
Yurt in Windham
4.98 out of 5 average rating, 117 reviews

Sebago Sunrise Yurt - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.

Guest favorite
The image features a studio layout with four sections. A cozy sitting area includes a blue sofa and armchair, facing a smart TV. A table set for dining is seen next to a modern kitchen. A spacious king bed is presented with decorative pillows, and a coffee table adorned with tasteful decor completes the scene.
Apartment in Westbrook
4.91 out of 5 average rating, 141 reviews

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

Top guest favorite
A spacious sleeping area features natural wood paneling and a high ceiling. A comfortable bed is dressed in light blue and white linens, accompanied by two decorative pillows. A wooden cabinet and a bedside lamp add functional elements, while a window allows soft light to fill the room.
Barn in Portland
5 out of 5 average rating, 473 reviews

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

Top guest favorite
The cozy cabin is illuminated by soft outdoor lights, enhancing its charming facade. The front porch features a seating area, with potted flowers adding a touch of nature. The surrounding grassy area includes stone steps leading towards the entrance, promoting a welcoming atmosphere.
Tiny home in Portland
4.95 out of 5 average rating, 531 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Guest favorite
Apartment in Westbrook
4.91 out of 5 average rating, 114 reviews

Cozy 2 Bedroom Apartment Close to Portland

This is a newly renovated two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a Pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Top guest favorite
A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.
Guest suite in Freeport
4.98 out of 5 average rating, 120 reviews

Studio Apartment in Freeport

Relax with your family in this modern studio apartment. Kids or adventurous adults will love climbing into the twin bed nook to read a book or sleep. Have a seat at the table to play a board game, eat a home cooked meal, or devour takeout. Lay in the king bed or sit on the couch to watch a movie or just relax. We are in a private wooded area just 5 minutes from downtown Freeport.

Guest favorite
Cabin in Freeport
4.95 out of 5 average rating, 103 reviews

Gorgeous A-frame in a quiet campground - 15

The Escape is a gorgeous A-frame cabin that features a wall of 18' wall of glass overlooking beautiful woods. It is set among the tranquil northern pines of the recently renovated campground of the Desert of Maine. The cabin is 11/10 romantic and has everything you need to enjoy a luxurious, relaxing outdoor experience. Disconnect from the world at this beautiful A-frame!

Popular amenities for Westbrook family-friendly rentals

When is the best time to visit Westbrook?

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Avg. priceG$35,155 GYDG$34,108 GYDG$31,597 GYDG$36,619 GYDG$41,014 GYDG$47,501 GYDG$62,776 GYDG$62,776 GYDG$45,827 GYDG$44,780 GYDG$41,432 GYDG$38,921 GYD
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Quick stats about vacation rentals that are family-friendly in Westbrook

  • Total vacation rentals

    Explore 40 vacation rentals in Westbrook

  • Nightly prices starting at

    Westbrook vacation rentals start at G$16,740 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,060 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Westbrook vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westbrook rentals

  • 4.8 Average rating

    Westbrook stays are highly rated by guests—averaging 4.8 out of 5!