
Kid-friendly holiday rentals in Oakland
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Oakland
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Oakland family-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!

Cute Midcoast Cottage w Hot Tub
We absolutely loved our stay, the house is very private and comfy. The master bathroom and kitchen were both really nice. Beds are very comfy as well. I would definitely recommend this place to anyone

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!

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.
Family-friendly apartment rentals

Fernald's Backside
We had a great stay at Sumners place. It's location is very cool being right downtown but at the same time it is quiet and peaceful. He has it set up with everything you need and more. We appreciated his friendliness and great communication!

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.

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! ❤️

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!
Family-friendly apartment rentals

6 miles from Sunday River with heated outdoor pool
Easy quick getaway for ski/snowboard trip

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

Riverbend Ski Condo < 3 miles to Sunday River
Great place to stay so close to Sunday river! Wonderful to be within close driving distance of the mountain. Comfortably slept 4 people for a weekend. Kitchen and bathroom were clean and had everything we needed! Would definitely recommend staying here for a ski trip or whatever else.

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.

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
$154 SGD 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 Holiday rentals
- Portland Holiday rentals
- Bar Harbor Holiday rentals
- Mid-Coast Holiday rentals
- Southern Maine Coast Holiday rentals
- Old Orchard Beach Holiday rentals
- Wells Holiday rentals
- Hudson Valley Holiday rentals
- The Hamptons Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Rentals with outdoor seating Oakland
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- House rentals Oakland
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- Family-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