
Kid-friendly holiday 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.
Holiday rentals for every style
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Popular amenities for Oakland kid-friendly rentals
Child-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.

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!

Hilltop Retreat with Hot Tub & Sauna near Downtown
Everything was as described and more! With a wonderful location close to town, good privacy, and so much space inside with many commodities we wouldn’t even think of. Even our dog had a fun filled week with us. We hope to visit again, it’s just the perfect home away from home. Couldn’t recommend a better place to stay.

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.

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.

Private Lakehouse, Firepit & Amazing Sunset Views
fantastic stay. clean and well equipped. the lake is even more beautiful than the pictures! Roman was very responsive and went above and beyond in providing helpful information about the area and place.
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
Nice place with a great location. It’s a quick walk to downtown Hallowell. Downtown has coffee shops,bakeries and restaurants. Good access to the rail trail for a nice walk along the river.

Apt above Ambition Brewing in Downtown Wilton
Enjoy stay beautiful lake , lots of Restaurants, and don't forget to stop at ambitions brewery and chaos coffee I've been here 32 years it's the best place

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.

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! ❤️

1820s Maine Cottage with Garden
We booked last minute and had such a relaxing one night stay here. Gorgeous little cottage with an insanely comfortable bed under the velux windows so you can look up at the trees! We loved it and it was perfect to break up our trip up the coast to Acadia. Really clean and comfortable and we loved watching TV with pizza and then playing a couple games! The bath was also very nice for a quick morning soak. Would really recommend it!
Child-Friendly Holiday Condos

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 holiday rentals that are kid-friendly in Oakland
Total rentals
20 properties
Nightly prices starting at
$185 AUD 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
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
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- Rentals with outdoor seating Oakland
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- House rentals Oakland
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- Kid-friendly rentals Kennebec County
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- 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
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Rockland Breakwater Light
- Three Island Beach
- Spragues Beach
- Eaton Mountain Ski Resort
- Pinnacle Park
- 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