Kid-friendly vacation rentals in Oakland

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Oakland kid-friendly rentals

Kid-friendly house rentals

Top guest favorite
A cozy living area features knotty-pine walls and a comfortable seating arrangement with a blue sofa. A small coffee table sits atop a textured area rug. A television is positioned on a media console, illuminated by a nearby lamp. Two windows with patterned curtains allow natural light to fill the space.
Home in Farmington
4.99 out of 5 average rating, 207 reviews

Farmington! Walk to town & trails! Family-Friendly

KarenRating, 5 stars2 weeks ago
Corey’s place was perfect for our long Memorial Day weekend in Farmington! He was very responsive to messages. The house was clean and decorated with adorable Maine memorabilia. We would definitely stay at Corey’s again!
Guest favorite
An outdoor fire pit is surrounded by eight colorful chairs, providing a cozy gathering spot amidst nature. The chalet-style house in the background features a metal roof and is set against a backdrop of trees, enhancing the tranquil ambiance.
Home in Sumner
4.96 out of 5 average rating, 135 reviews

Quiet and Private in Oxford Hills – Dog Friendly!

RaijueneaRating, 5 stars3 weeks ago
Amazing place, host was super kind and accommodated my family’s last minute booking since we were cancelled on twice that week! We are super happy we found this adorable beautiful place that ended up being better than the other places would have been anyway!
Top guest favorite
Home in Bridgton
5 out of 5 average rating, 103 reviews

Wren Cabin + Wood fired Sauna

WillRating, 5 stars1 week ago
Our stay was so relaxing. The house is very comfortable and we felt at home right away. Kitchen had everything we needed to prepare meals. The sauna is absolutely magical and the lake was quiet and peaceful. Check in/out was a breeze. Perfect spot for a relaxing long weekend with zero stress.
Guest favorite
Home in Belgrade
4.86 out of 5 average rating, 21 reviews

Family's Paradise: 3BR/2BA,Game Room & Lake Access

AnthonyRating, 5 stars3 months ago
Great rental property in a great place.
Superhost
A collage captures the serene waterfront home amid autumn foliage. Images depict fishing activities, a turtle sunbathing, grilling with sausages, and a tranquil evening scene with a starry sky reflecting on the water.
Home in Pittsfield
4.82 out of 5 average rating, 124 reviews

Cozy Waterfront Home With Breathtaking Views!!!

JessicaRating, 5 stars5 days ago
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!
Top guest favorite
A spacious dock extends over a calm lake, adorned with colorful Adirondack chairs facing the water. The sky is illuminated with soft hues of purple and orange as the sun sets, creating a serene atmosphere at dusk.
Home in Oakland
4.94 out of 5 average rating, 48 reviews

Lake Front with Amazing Sunset on McGrath Pond

Kristen HRating, 5 stars8 months ago
This place was awesome for our family. My younger daughter and husband have a toddler and the accommodations were perfect. The dock and all of the water sports equipment was a huge hit. We kayaked , and fished. My oldest daughter did a plunge in the lake ( mind you it’s October!!!). Every morning I sat on the dock watched the sun come up and enjoyed the views and wildlife. Having a properly equipped kitchen was an added bonus. The bedrooms were very comfortable and we like we were at home. Dry peaceful and quiet. Looking forward to a return trip.
Guest favorite
A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.
Home in Augusta
4.96 out of 5 average rating, 156 reviews

Lakefront: Private Hot Tub, Sauna & Free Massages!

MichelleRating, 5 starstoday
We had two nights to spend in Maine after a week long trip to Quebec. The lake house was a wonderful place to unwind after our busy trip to Canada. We spent our full day parked in the yard, enjoying the boats provided, reading, playing bags, and just sunning. It was a gorgeous day, and we loved it. The house is spacious, very well-stocked, and has many little amenities to make it feel like home. Highly recommend!
Guest favorite
A sleeping area features a light blue headboard paired with a patterned quilt and striped pillows on a spacious bed. A lamp sits on a bedside table next to the bed. Soft light enters through the partially open window, enhancing the calming ambiance.
Home in Lisbon
4.94 out of 5 average rating, 428 reviews

Unplug at a Beachy Bolthole with Classic New England Style

MatthewRating, 5 stars1 day ago
Stayed here for 1 night to cap off a Maine coastal trip and it was a perfect place to unwind and relax. Good walkable food options and very comfortable bed.

Kid-friendly apartment rentals

Top guest favorite
An inviting entrance features a white door with glass panes, framed by red trim. A decorative wheel hangs on the wall, while a flowering planter adds a touch of greenery. Sunlight casts soft shadows on the rustic shingled exterior.
Apartment in Boothbay
4.97 out of 5 average rating, 323 reviews

Sunnymeade

SamanthaRating, 5 stars4 days ago
Robert’s place was the perfect getaway for me calm, quiet, and peaceful. Everything was perfect, the space was cozy and neat, it had everything I needed for a few days away. Quick drive to the harbor with lots to do if one chooses. Hoping to make it back there soon.
Top guest favorite
A spacious living area is highlighted by hardwood flooring and tasteful furnishings. A gas fireplace adds warmth, while natural light filters through the large windows with soft treatments. A comfortable seating arrangement is complemented by a decorative side table and a modern television mounted on the wall.
Apartment in Hallowell
4.94 out of 5 average rating, 309 reviews

High End Apartment in Downtown Hallowell

PeterRating, 5 stars2 months ago
This place was comfortable, well-provisioned, and very well located. Pam was very responsive as well. Good stay!
Guest favorite
A spacious living area features light teal walls and two large windows allowing natural light to fill the room. A soft gray armchair and a brown recliner are positioned next to a wooden coffee table. The entrance door is framed with white trim.
Apartment in Wilton
4.93 out of 5 average rating, 264 reviews

Apt above Ambition Brewing in Downtown Wilton

JoanneRating, 5 stars1 month ago
Great spot at the center of Wilton. Comfortable bed. Close to restaurants. Responsive and courteous host.
Guest favorite
A cozy living area is highlighted by an electric fireplace set against a stone wall, providing a warm focal point. Two glasses of red wine sit on a rustic glass table, accompanied by decorative wood coasters and a small plant nearby.
Apartment in Kingfield
4.96 out of 5 average rating, 363 reviews

On The River 2 with Lucy the resident cat

IsaahRating, 5 stars3 weeks ago
we always look forward to having a good stay here when its 1 day or a couple. Patricia is always friendly and always helpful for the area. Great host and great spot. highly recommend
Top guest favorite
An open living space features a cozy seating area with a light-colored sofa and a decorative area rug. A spacious bed is placed in one corner, accompanied by soft bedding. The kitchenette is visible in the background, along with a doorway leading to a bathroom.
Apartment in Gardiner
4.97 out of 5 average rating, 113 reviews

The Escape on Elm

KarenRating, 5 stars1 week ago
Beautifully decorated, comfortable bed, clean and in a nice neighborhood. Easy check in and check out. Responsive host. I would stay here again!
Top guest favorite
The lodge features a stately exterior with multiple wings, framed by lush greenery and neatly manicured landscaping. A spacious driveway provides access to the entrance, with sunlight illuminating the building's classic design.
Apartment in Pittsfield
4.99 out of 5 average rating, 112 reviews

The Lodge

MelodyRating, 5 stars2 weeks ago
I cannot say enough about Nancy, the unit I stayed in, or her hospitality! This apartment was perfect and cozy for my visit, with lots of personal touches and extras - if you need it, she’s already thought of it and has it ready for you. She was also very accommodating when my flight was cancelled and I had to shift my days around a bit. The personal touches were perfect - I had farm fresh eggs for breakfast and some delicious muffins too. A wonderful stay, thank you! I will most definitely be back! ❤️
Guest favorite
The kitchen features wooden cabinets and a granite countertop. A round dining table with four chairs is situated centrally. Stainless steel appliances, including a refrigerator and a stove, are visible, along with various kitchen utensils and supplies arranged on the countertop.
Apartment in Augusta
4.82 out of 5 average rating, 117 reviews

Downtown Augusta - 2 Bedroom - Newly renovated!

TheodoraRating, 5 stars1 day ago
Everything you need for a lovely stay. Walkable to downtown and river trails and the most comfortable beds I’ve ever encountered on Airbnb!
Top guest favorite
A cozy living room features a gray sofa with decorative pillows and a light coffee table in the center. A desk and chair set is accompanied by two windows dressed with tailored shades. Natural light illuminates warm wood floors and potted plants add a touch of greenery.
Apartment in Bath
4.97 out of 5 average rating, 101 reviews

1820s Maine Cottage with Garden

DawnRating, 5 stars1 week ago
My partner and I absolutely loved staying here! We came to Bath for the weekend and feel so lucky to have sound this spot. Carrie was a great host, and even loaned us an umbrella when the weekend rain would have otherwise dampened our plans to walk into town. The place was tastefully furnished (unlike some of the cheap IKEA-overload spots we've stayed in before) and showed signs of beautiful craftsmanship and attention to detail throughout. The bedroom was dreamy, and the clawfoot tub in the bathroom made for a relaxing and romantic evening. The kitchen was stocked with just about everything we needed (although a larger cutting board would have made out meal prep a bit easier), and we enjoyed watching all kind of wildlife in the backyard as we ate our meals. After our first sty here we are sure we'll be back next year. Thank you Carrie and family!!

Kid-friendly condo rentals

Guest favorite
The kitchen area features navy cabinetry and stainless steel appliances, including a refrigerator and coffee maker. A dining table with wooden chairs is positioned nearby, and decorative elements like a patterned rug enhance the warm, wooden interior.
Condo in Carrabassett Valley
4.95 out of 5 average rating, 133 reviews

Ski-In/Ski-out, Sunny, On-Mountain Getaway!

DougRating, 5 stars2 months ago
Good location, easy access to the hill by either driving or shuttle. The condo was fine for our group of four. Kitchen had everything to cook for that many. Very comfortable. thanks
Guest favorite
A cozy living area features a comfortable sofa and an accent chair beside a stylish table. A propane fireplace is framed by wooden shelves displaying decorative items. A flat-screen TV is positioned on a wooden console, with board games and books available for guest use.
Condo in Carrabassett Valley
4.96 out of 5 average rating, 101 reviews

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio

JeremyRating, 5 stars1 month ago
This was an excellent condo for us before and after the Sugarloaf road race. It was very clean and welcoming. The hosts were attentive and proactive with information. We would absolutely stay here again!
Top guest favorite
A bright kitchen area features four wooden stools set at a white counter, illuminated by natural light from large windows. Soft yellow walls complement white cabinetry, with a granite countertop adding a touch of elegance to the space.
Condo in Damariscotta
4.89 out of 5 average rating, 164 reviews

River Escape - Studio Apt. with River Access

MarlaRating, 5 stars1 month ago
Lovely stay in a cozy place during a harrowing move. Cozy place provided just what we needed.
Guest favorite
An aerial view captures a spacious condo surrounded by lush greenery and the Damariscotta River in the background. A relaxing pool is visible in the foreground, alongside a parking area with multiple vehicles. The serene landscape contributes to a calming atmosphere.
Condo in Damariscotta
4.96 out of 5 average rating, 47 reviews

Lovely 2 bedroom riverside condo with pool

AnnaRating, 5 stars8 months ago
Lovely, clean apartment with a terrific location! We highly recommend and hope to return soon--maybe even for Pumpkinfest again next year. Thank you especially for the extra blankets, that was such a kind gesture.
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, 179 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

HannahRating, 5 stars1 month ago
Great place to stay in Brunswick! Extremely walkable to the downtown restaurants and shops. Clean and bright space with spacious bedrooms (enough space to throw a pack-and-play in one of the bedrooms). Beds were comfortable and living room/kitchen good for socializing! Bonus — you can also access the Androscoggin River path for a nearby dose of nature and water. This is the second location of Spencer’s we’ve stayed in (the other about two years ago) and both stays were awesome. Highly recommend for a trip to Brunswick!
Top guest favorite
An open concept space features a modern kitchen with light wood paneling and sleek stainless-steel appliances. A multi-colored granite countertop serves as a dining area with four teal stools. Visible in the background is a cozy seating area and an entry to a bedroom.
Condo in Belfast
5 out of 5 average rating, 17 reviews

Harbor View Cottage Unit A 2 bedroom downtown

BrandonRating, 5 stars9 months ago
What a beautiful location and house. There’s nothing better than sitting in the living room or front porch and being able to see the Belfast Bay. The house is very clean and neat. Beds are comfortable, shower is very hot. Don’t miss the sunrise in the mornings. Overall this is one of our favorite places we have stayed in Belfast.
Guest favorite
An open-concept living space is observed from above, featuring a wooden dining table surrounded by red chairs. A ceiling fan is prominently displayed, with a cozy seating area visible. Light enters from large windows, illuminating the warm colors of the decor.
Condo in Greenwood
4.98 out of 5 average rating, 43 reviews

Spacious Bike/Golf/Ski Condo in Mt. Abram Village

JanetteRating, 5 stars4 months ago
Michael was an attentive host; checked in with me several times during our stay. His instructions and requests were very clear and easy to follow. We had no issues during our stay and loved the location. I would recommend Michael as a host to anyone looking to stay in the area.
Top guest favorite
A spacious log cabin is surrounded by young trees and lush greenery. The exterior features a combination of wood textures and a welcoming porch. A gravel area in the foreground provides access to the cabin, enhancing the natural setting.
Condo in Carrabassett Valley
4.96 out of 5 average rating, 90 reviews

First Tracks at Sugarloaf

SarahRating, 5 stars1 month ago
Is is the second time we’ve stayed here and our whole family loves Aka’s place. We feel right at home on the mountain. What an amazing place and a gracious host!

Quick stats about vacation rentals that are kid-friendly in Oakland

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$25,078 GYD before taxes and fees

  • Total number of reviews

    830 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland
  6. Kid-friendly rentals