Family-friendly vacation rentals in Westbrook

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Popular amenities for Westbrook family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A modern farmhouse is situated on elevated land, surrounded by trees. Its white exterior is complemented by large windows that reflect in the calm water below. The scenic scene is framed by lush greenery, creating a serene atmosphere.
Home in Woolwich
5 out of 5 average rating, 43 reviews

Amazing view, eagles, hot tub, 1 mi walk from Bath

GregoryRating, 5 stars2 weeks ago
Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.
Top guest favorite
Apartment in Falmouth
4.91 out of 5 average rating, 200 reviews

Falmouth 3br near Town landing

EllenRating, 5 stars1 week ago
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.
Guest favorite
A wood-fired cedar hot tub sits on a deck, surrounded by trees. Two folding chairs are placed beside the hot tub, offering a serene spot for relaxation. The structure's screened-in porch provides a view of the surrounding nature.
Treehouse in Georgetown
4.97 out of 5 average rating, 341 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

JustinRating, 5 stars2 weeks ago
Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!
Superhost
A hot tub is positioned under a wooden pergola, surrounded by a spacious patio area. Red Adirondack chairs are arranged nearby, facing a grassy yard bordered by trees. Soft sunlight filters through the foliage, enhancing the inviting setting.
Home in Conway
4.84 out of 5 average rating, 241 reviews

Best backyard in N Conway w/ hot tub, game room...

KatherineRating, 5 stars4 months ago
We spent a lovely few days at this property enjoying the winter weather at its finest. The house is close to everything but still felt private and cozy. A great choice for families!
Superhost
A spacious outdoor pool area is seen, surrounded by a paved deck. Sun loungers are positioned neatly along the perimeter, with blue umbrellas providing shade. A clubhouse with a large deck overlooks the pool, set against a backdrop of trees.
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars7 months ago
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.
Guest favorite
The three-story beach house features a prominent grey exterior with multiple large windows allowing natural light. A spacious patio is surrounded by landscaped greenery, offering seating areas with chairs and sun beds. Balconies extend from the upper levels, providing outdoor spaces with relaxing views.
Home in Old Orchard Beach
4.96 out of 5 average rating, 147 reviews

Luxury 6 bedroom Beach House 50 ft from beach

JacobRating, 5 stars3 weeks ago
The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.
Guest favorite
A private deck area showcases a hot tub, emitting a soft blue light. Two chairs are positioned nearby, with a decorative cushion displayed on one. Lattice fencing and greenery provide privacy, creating an inviting setting for relaxation at night.
Apartment in Topsham
4.87 out of 5 average rating, 551 reviews

Cozy hot tub haven

ColeRating, 5 stars2 days ago
Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.
Superhost
Two wooden chairs are positioned on a deck, facing a serene pond surrounded by vibrant autumn foliage. A small table rests between the chairs, and the expansive sky is filled with clouds, adding to the tranquil atmosphere of the natural setting.
Home in Harrison
4.9 out of 5 average rating, 308 reviews

Riverfront Luxury in the woods, Million $ Views.

KristieRating, 5 stars2 weeks ago
Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

Family- and pet-friendly home rentals

Guest favorite
A rustic cottage with dark wood siding is surrounded by greenery. Two adirondack chairs are positioned on the grassy lawn in front of the house, which features large windows and a spacious deck. Trees provide shade on a bright, sunny day.
Home in Yarmouth
4.81 out of 5 average rating, 136 reviews

Kelley's Ocean View Cottage

LindaRating, 5 stars7 months ago
Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.
Guest favorite
A spacious deck is highlighted by a large red umbrella over a table, surrounded by four wicker chairs. Lush greenery and colorful flowering bushes create a natural backdrop, enhancing the outdoor seating area in the yard.
Guest suite in Freeport
4.73 out of 5 average rating, 581 reviews

Freeport Village Sunny Studio

CaitlinRating, 5 stars2 weeks ago
What stood out the most to me was how responsive Jennifer was, even before booking. It just showed how much she cares about her rental. Her and her family were very accommodating, the rental was clean and had everything we needed, and the location was perfect for a trip to Freeport! Would highly recommend! 😊
Guest favorite
A cozy bedroom features a spacious bed with a floral quilt and decorative pillows. Natural light filters through curtains adorned with floral patterns, enhancing the inviting atmosphere. A bedside table and a wooden dresser are present, contributing to the room's functionality.
Apartment in Old Orchard Beach
4.93 out of 5 average rating, 199 reviews

The Upstairs Moose

StacyRating, 5 stars6 months ago
Normand and his wife were simply amazing. From the eggs and snacks that were waiting for us when we arrived to the homemade cookies on our check out. The place was very cozy and comfortable with tons of toys and games for kids and adults. Normand was very accommodating to any request and even helped me chase the puppies when they accidently got out. I would highly recommend this!
Guest favorite
The exterior of a Victorian farmhouse is showcased, featuring classic white siding and multiple large windows. Lush green trees frame the house, while vibrant pink and purple flowers add color to the front yard. A covered porch invites relaxation.
Apartment in Lisbon falls
4.94 out of 5 average rating, 467 reviews

Charming Victorian farmhouse 1880's bedrooms-2

KandiceRating, 5 stars3 weeks ago
Thoughtfully designed and appointed place - has all the things you need and Marcia makes it very easy to get in and check out. Easy to get to Lewiston, Brunswick, Portland and everywhere in between!
Guest favorite
A charming white cottage with a sloped roof is situated near the water's edge. Orange window boxes add a pop of color to the exterior, while a stone patio features several wooden chairs. Lush greenery surrounds the property, providing a natural backdrop.
Home in Bath
4.91 out of 5 average rating, 345 reviews

Gorgeous Studio on the Kennebec

AlexandraRating, 5 stars6 days ago
Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!
Guest favorite
Two vintage-style homes are set against a backdrop of tall trees under a clear blue sky. One home is slightly elevated, showcasing a classic white exterior with dark shutters, while the other features a wraparound porch and larger windows, blending harmoniously with the natural landscape.
Apartment in Freeport
4.92 out of 5 average rating, 227 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

GemmaRating, 5 stars2 months ago
A beautiful and cozy space with lovely natural light and generous room to spread out. The full kitchen is equipped like a real home, with everything from basic pots and pans to whisks and even nut crackers! A great place for cooking full meals. A nice quiet location, even with its relative proximity to a regularly-traveled road. I'm sensitive to noise and was never bothered by sounds of traffic. Pettengill Farm is only a few minutes up the road, a beautiful place to walk for both dogs and humans and really easy to access multiple times a day. Mandana was always very responsive to communication, and when there was a glitch with Airbnb's fee calculation she was extremely helpful and approachable and took care of it immediately.
Superhost
An open concept kitchen and dining area is visible, featuring a red retro fridge, white cabinetry, and a wooden dining table with black chairs. Natural light is provided by several windows, illuminating a minimalist decor style with a vase of flowers and a laptop on the table.
Condo in Brunswick
4.85 out of 5 average rating, 180 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

BonnieRating, 5 stars3 weeks ago
We stayed at a few of Spencer's places while our child was at Bowdoin college. The places are lovely and convenient and made visiting our child a pleasure.
Top guest favorite
A bright common area is visible, featuring a dark sofa adorned with yellow cushions, a wooden coffee table, and a dining table surrounded by light-colored chairs. Large windows allow natural light to fill the room, with plants positioned near the windowsill.
Apartment in East End
4.97 out of 5 average rating, 464 reviews

Bright and cozy Munjoy Hill neighborhood apartment

KathleenRating, 5 stars2 weeks ago
This home was fabulous! The space was clean, lovely, and so comfortable. Additionally the neighborhood offered but walks in nature and restaurants/stores. I wish I could go back next month!

Family-friendly home rentals with a pool

Superhost
A historic lake-front cottage is presented with its red siding and white trim, featuring numerous windows that enhance natural light. A cupola tops the building, while a porch extends along the front. A sandy area in front leads to the water.
Cottage in Poland
4.61 out of 5 average rating, 18 reviews

Lake Beach House at Poland Spring Resort

Erin Rating, 5 stars10 months ago
Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!
Top guest favorite
A vibrant view captures the amusement park, featuring a large Ferris wheel and colorful attractions. The beach stretches in the background, illuminated by a soft, pastel sunset. A lively crowd gathers below, enjoying the bustling atmosphere of the town square.
Condo in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 months ago
This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!
Guest favorite
A large outdoor pool area is surrounded by lounge chairs in vibrant colors. The pool is complemented by neighboring buildings with multiple windows, providing a welcoming atmosphere. The concrete patio offers ample space for relaxation and sunbathing, with a barbecue area visible in the background.
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones
A serene lakeside view captures a sunset reflected on calm water. Silhouetted trees frame the scene, with a picnic table and a bench positioned on the sandy shore. Gentle waves are visible, and a distant boat rests peacefully as the sky radiates soft colors.
Cottage in Frye Island
5 out of 5 average rating, 10 reviews

Sebago Lake - A-frame cottage on Frye Island

TarynRating, 5 stars10 months ago
Perfect little spot on Frye Island! Great location, walking distance to our favorite beach on island as well as the general store. House was clean, comfortable, just as described. We enjoyed our stay!
Guest favorite
A refreshing pool area is surrounded by well-kept landscaping and seating options. Two blue umbrellas provide shade over metal chairs and tables. Colorful pool floats are positioned in the clear water, and a charming white structure is visible in the background.
Apartment in Falmouth
4.97 out of 5 average rating, 93 reviews

Poolside Suite-Gateway to Portland

CameronRating, 5 stars3 weeks ago
Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.
Guest favorite
An aerial view of a spacious backyard showcases a well-maintained heated pool surrounded by a patio area with seating. Lush greenery and trees frame the property, enhancing the outdoor space, while a shaded fire pit area and landscaped garden beds are visible.
Home in Portland
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown
A charming wooden cabin is framed by lush green trees, creating a serene forest setting. A small shed is located to the side, while a grill complements the porch area, featuring wooden steps and adjacent seating. Natural sunlight gently illuminates the scene.
Chalet in Frye Island
4.76 out of 5 average rating, 87 reviews

Cabin in Paradise

ChiaraRating, 5 stars9 months ago
My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.
Guest favorite
A spacious pool area features clear blue water, surrounded by a well-maintained concrete deck. Lounge chairs are arranged along the sides, providing ample seating. In the background, a clubhouse with large windows is framed by greenery, offering a shaded space for relaxation.
Home in Bridgton
4.88 out of 5 average rating, 162 reviews

Moose Pond Mountain Escape

PhilRating, 5 stars2 days ago
We had a great time at Jim and Gwens place in Knight's Hill. The amenities were great and the location provided us with everything we were looking for near Moose Pond. Would highly recommend.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$18,838 GYD before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

Destinations to explore