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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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, 393 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 Deering Center

4.84 out of 5 average rating, 555 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.

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, 234 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 Deering Center

4.92 out of 5 average rating, 162 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 hyper-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

Home in Hollis

4.99 out of 5 average rating, 428 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.

Guest favorite

A modern kitchen with sleek cabinetry and a central wooden table is featured. Two metal chairs are positioned at the table, and stainless steel appliances are visible. Natural light enters through large glass doors, illuminating the space and highlighting decorative cushions on a nearby sofa.

Apartment in East End

4.9 out of 5 average rating, 403 reviews

Hip & Cozy, high end Modern Design

Hip, modern retreat. This is your pied a terre for your Portland visit. High quality new construction, private, sweet unit, with wide-plank white oak and concrete floors, huge windows, full kitchen, tasteful design. In Portland's coveted Munjoy Hill neighborhood, you will be a block and half from the spectacular eastern Promenade, 5 minute walk to shops and restaurants at the top of 'the Hill', and 20 minute walk to the Old Port and all Portland has to offer.

Guest favorite

A private patio area is enclosed by a wooden fence, featuring a small dining table with two chairs. Potted flowers and ferns add color to the space, while string lights create a cozy ambiance. Natural light filters through leafy trees above.

Apartment in Rosemont

4.8 out of 5 average rating, 374 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

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

4.96 out of 5 average rating, 478 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

Guest favorite

A cozy living room features a leather couch adorned with vibrant red pillows and a soft blue throw. A wooden coffee table sits in front, accompanied by a designer easy chair. Natural light filters through large windows, illuminating the space.

Guest suite in South Portland

4.92 out of 5 average rating, 253 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

Top guest favorite

The charming farmhouse features white clapboard siding and a gabled roof. A welcoming front porch is adorned with red steps and surrounded by lush greenery, creating an inviting entrance. Windows with white trim allow natural light to fill the interior.

Guest suite in Rosemont

4.9 out of 5 average rating, 164 reviews

Welcome Home to Sunny View ~ A Home away from home

Our century old farmhouse is 10 minutes from downtown Portland in the friendly Rosemont neighborhood. The space is the upstairs of our house and consists of a queen bedroom A small twin bed room - and a common living area that greets the morning sun Peaceful and relaxing. The suite will sleep one couple Or two singles comfortably.