
Kid-friendly vacation rentals in Oakland
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Oakland
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakland kid-friendly rentals
Kid-friendly house rentals

Farmington! Walk to town & trails! Family-Friendly
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!

Quiet and Private in Oxford Hills – Dog Friendly!
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!

Wren Cabin + Wood fired Sauna
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.

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Great rental property in a great place.

Cozy Waterfront Home With Breathtaking Views!!!
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!

Lake Front with Amazing Sunset on McGrath Pond
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.

Lakefront: Private Hot Tub, Sauna & Free Massages!
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!

Unplug at a Beachy Bolthole with Classic New England Style
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

Sunnymeade
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.

High End Apartment in Downtown Hallowell
This place was comfortable, well-provisioned, and very well located. Pam was very responsive as well. Good stay!

Apt above Ambition Brewing in Downtown Wilton
Great spot at the center of Wilton. Comfortable bed. Close to restaurants. Responsive and courteous host.

On The River 2 with Lucy the resident cat
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

The Escape on Elm
Beautifully decorated, comfortable bed, clean and in a nice neighborhood. Easy check in and check out. Responsive host. I would stay here again!

The Lodge
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! ❤️

Downtown Augusta - 2 Bedroom - Newly renovated!
Everything you need for a lovely stay. Walkable to downtown and river trails and the most comfortable beds I’ve ever encountered on Airbnb!

1820s Maine Cottage with Garden
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

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

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio
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!

River Escape - Studio Apt. with River Access
Lovely stay in a cozy place during a harrowing move. Cozy place provided just what we needed.

Lovely 2 bedroom riverside condo with pool
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.

New 2BR 2King beds Private Apt Downtown Brunswick
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!

Harbor View Cottage Unit A 2 bedroom downtown
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.

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

First Tracks at Sugarloaf
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
- China Vacation rentals
- Portland Vacation rentals
- Bar Harbor Vacation rentals
- Mid-Coast Vacation rentals
- Southern Maine Coast Vacation rentals
- Old Orchard Beach Vacation rentals
- Wells Vacation rentals
- Hudson Valley Vacation rentals
- The Hamptons Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Québec City Vacation rentals
- Rentals with a washer and dryer Oakland
- Rentals with lake access Oakland
- Pet-friendly rentals Oakland
- Rentals with a fire pit Oakland
- Rentals with outdoor seating Oakland
- House rentals Oakland
- Family-friendly rentals Oakland
- Waterfront rentals Oakland
- Rentals with a fireplace Oakland
- Rentals with a kayak Oakland
- Rentals with a patio Oakland
- Kid-friendly rentals Kennebec County
- Kid-friendly rentals Maine
- Kid-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Samoset Resort
- Saddleback Ski Mountain Maine
- Belgrade Lakes Golf Club
- Sugarloaf Golf Club
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Pinnacle Park
- Spragues Beach
- Lost Valley Ski Area
- Pebble Beach
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Black Mountain of Maine
- Farnsworth Art Museum
- The Camden Snow Bowl
- Martindale Country Club