
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!

Carriage House
Beautiful place to stay! Very peaceful. Loved the carriage house.

Classy AF Home, walk across the street to Colby!
The photos don’t do this place justice! It is extremely pretty and bigger than I thought! Its location is perfect and made for an easy reunion weekend at Colby!

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
the perfect cabin nestled in the woods in a quaint town! We spent the week in Emily’s peaceful cabin and it was the perfect Maine getaway. The pond is a highlight! I loved getting to stay in this lovely cabin.

Peaceful Getaway at The Ledges
Our stay at Margaret's home was very relaxing and comfortable. Pristine bathroom, kitchen and bedding. The lake view was so much more than we anticipated. It was serene, peaceful, and breathtaking. She went out of her way to answer questions for us about the area, and we left feeling like we just gained a new friend. Jeff and Donna

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

Mystical Mary Howe Room, Downtown Damariscotta
Such a great place to stay! Thank you so much

Loft Retreat
This Airbnb was exactly as listed. Everything is updated, very clean, and comfortable. Jordana was very responsive and accommodating. I would stay here again.

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

Finding Joy
We enjoyed our time here. Brenda was very responsive and helped us out when we needed accommodations pretty short notice. The area is private and peaceful, it was just what we needed to rest up and recharge for busy traveling days.

The Escape on Elm
This was my second stay at this location, and again, we really enjoyed our stay! Everything is as described. Very cozy place. There is a nice park close by if you have kids along with you.

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! ❤️

Two Bedroom Mid Century Modern Downtown Apartment
A great location and exceptionally clean, with small details like snacks and wine available. Very comfortable beds, a deep tub and good vibes.

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!
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
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.

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
Second time there in spring and summer had an awesome time and Eka was unbelievable
Quick stats about vacation rentals that are kid-friendly in Oakland
Total rentals
20 properties
Nightly prices starting at
R2,163 ZAR 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 a fire pit Oakland
- Rentals with a fireplace Oakland
- House rentals Oakland
- Pet-friendly rentals Oakland
- Waterfront rentals Oakland
- Rentals with lake access Oakland
- Rentals with a kayak Oakland
- Rentals with a patio Oakland
- Family-friendly rentals Oakland
- Rentals with outdoor seating 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
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Saddleback Ski Mountain Maine
- Sugarloaf Golf Club
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Hermon Mountain Ski Area
- Rockland Breakwater Light
- Three Island Beach
- Spragues Beach
- Pinnacle Park
- Eaton Mountain Ski Resort
- Narrow Place Beach
- Lost Valley Ski Area
- The Camden Snow Bowl
- Bear Island Beach
- Pebble Beach
- Black Mountain of Maine
- Martindale Country Club
- Farnsworth Art Museum