Family-friendly vacation rentals in Westbrook

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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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Superhost

The exterior of a classic Victorian building is displayed, characterized by its wooden siding painted in muted grey. Large windows and unique architectural details enhance its charm. Surrounding greenery adds a touch of nature to the urban setting, and a gravel path leads to the entrance.

Apartment in West End

4.78 out of 5 average rating, 734 reviews

BEST location! HUGE 1 bedroom downtown Portland

License#STHR0011152019 Spacious 1 bedroom w/living room, eat-in kitchen and bath in ideal Portland peninsula location, walk to all. situated on the edge of the west end and downtown. 2 blocks from the ocean. Walk everywhere in this central, historic, perfect location. Easy street parking. Simple furnishings, older retro flair. 2nd floor of 3 unit Victorian on dead end, quiet street. Queen bed. There is no parking but often spaces are available on this dead end street. Note steep steps going up

Guest favorite

A stone pathway leads to a garden-level entrance featuring a glass-paneled door surrounded by lush greenery. Stone steps are nestled amongst various plants and natural stones, creating an inviting approach to the suite.

Guest suite in East End

4.9 out of 5 average rating, 394 reviews

Garden Suite @ A Peaceful Oasis on Munjoy Hill

Spacious garden-level suite in an prime location, perfect for couples or solo travelers. Features tasteful art, contemporary furnishings, a queen bed, kitchenette, seating area, and bathroom with shower. LOCATION! Just a 5-minute walk to the Eastern Promenade with its food trucks, beach and scenic trails. Nearby you'll find bakeries, cafes, world-class restaurants and popular breweries. Just a 15-minute walk to the Old Port. At the end of the day, come back and relax at A Peaceful Oasis.

Superhost

A cozy living area is displayed, featuring a gray sofa adorned with patterned cushions. A modern floor lamp provides warm lighting. A small side table holds a decorative plant, and a minimalist clock is mounted on the wall. Natural light illuminates the space.

Apartment in Portland

4.84 out of 5 average rating, 557 reviews

Clean & Safe Apt w/Parking-Close to Downtown

Your cute, cozy one bedroom apartment is close to all that Portland has to offer! Your home away from home, you have 1 GBPS Wifi, the fastest Portland offers along with a comfortable desk to work from. Centrally located, the space it is a short drive to all of the great restaurants, bars, shops, parks and more! It is close to the 295-N ramp (Freeport outlet shopping is just a few exits down).Our location blends city living with that “just-off-the-beaten-path” feel that offers pleasant rest.

Top guest favorite

A spacious bedroom is furnished with a king-size bed featuring a plaid bedding set. Two windows allow natural light to enter, complemented by a bedside lamp. Wooden accents, including a wardrobe and a small table, enhance the room's warm ambiance.

Guest suite in Freeport

4.97 out of 5 average rating, 237 reviews

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Guest favorite

A spacious yard features a hammock set up for relaxation, accompanied by a fire pit area. The light yellow house stands in the background, offering multiple levels and direct access to outdoor spaces. Lush greenery surrounds the property, contributing to a serene outdoor setting.

Guest suite in Westbrook

4.93 out of 5 average rating, 237 reviews

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, 300Mbit wifi, smart TV, heat, ping pong, darts, and much more! 15 mins downtown Portland ($15 Uber) 1 mile from I-95 11 mins from the airport We will give you awesome tips on everything in the area and beyond!

Guest favorite

A comfortable armchair is positioned near a closet with shelves displaying books and board games. A dog bed is situated on the floor, providing a cozy space for pets. Light hardwood floors enhance the warmth of the room, complemented by neutral wall tones.

Apartment in Westbrook

4.88 out of 5 average rating, 111 reviews

Cozy 3BR | Pet Friendly | Near Portland | Parking

This 3-bedroom apartment in a quiet Westbrook neighborhood offers a bright, pet-friendly stay just 15 minutes from downtown Portland. With a full kitchen, private workspace, and plenty of natural light, it’s a great fit for families, professionals, or small groups. Key Amenities: • 3 queen beds + queen air mattress • Full kitchen • Smart TV, board games, and books • In-unit washer & dryer • 1 full bathroom • Keurig • Free driveway + street parking • Pet-friendly • Smart lock entry

Top guest favorite

A spacious backyard features a landscaped area with vibrant flowers and stone terraces. The home, set above, includes an elevated deck shaded by a canopy. Lush greenery surrounds the property, providing a sense of seclusion in a serene environment.

Home in Gorham

4.99 out of 5 average rating, 153 reviews

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Guest favorite

A serene bedroom space features a metal frame bed dressed in a quilted coverlet and decorative pillows. A wooden nightstand holds a lamp and a book, while a vintage chair sits nearby. A window allows natural light to brighten the room, enhancing its calm atmosphere.

Apartment in Portland

4.92 out of 5 average rating, 163 reviews

Inn@Norwood large private 2 br suite

3rd floor walk-up large 2 br suite all yours Spacious lr/dr kitchenette no range/oven or large fridge Private bath hi speed wifi secluded relaxing deck quiet neighborhood contact host for very reasonable off-season student/visiting professional rates Public trans plentiful safe street parking great restaurants parks nearby downtown Portland bus/train station airport colleges 2 mile walk or short ride Come to the Inn to relax in privacy enjoy your event & explore Maine

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 429 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Superhost

A spacious living area features comfortable seating, a dining table, and a fireplace. Natural light filters through large windows, highlighting the warm wood floors. The connected kitchen showcases modern appliances and a clean, airy layout, creating an inviting social space.

Apartment in West End

4.79 out of 5 average rating, 627 reviews

Sunny Downtown 2 Bed Apt, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. Location location location! This apartment is centrally located in the trendy West End neighborhood of Portland, minutes away from great restaurants, coffee shops, museums and a 15-minute walk or a 5min taxi ride to the Old Port. An off-street parking spot is included. The apartment entry is entirely keyless and painless!

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

4.96 out of 5 average rating, 481 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 when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

Superhost

The image presents a scenic view of a traditional working farm, featuring a large barn with a distinctive red roof and a white farmhouse. Surrounding greenery includes tall grass and trees, contributing to the rural atmosphere.

Apartment in Hollis Center

4.83 out of 5 average rating, 335 reviews

Lily Brook Farm, Hollis, Maine

One bedroom apartment on horse/sheep farm in Hollis, Maine. View of farm from living room, bedroom on second floor up very steep farm stairs. One Queen comfy bed. There is a day bed in the living room. 21 miles from Portland and Kennebunkport. The farm is on rt 35. Cars can go by fast, they always break the speed limit. Lots of peace out the back door but be aware this is not way out back away from the road.