Kid-friendly holiday rentals in Oakland

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Oakland kid-friendly rentals

Child-friendly house rentals

Top Guest favourite
Home in Farmington
4.99 out of 5 average rating, 207 reviews

Farmington! Walk to town & trails! Family-Friendly

KarenRating, 5 stars3 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 favourite
Home in Farmington
4.97 out of 5 average rating, 222 reviews

Carriage House

CarlaRating, 5 stars2 weeks ago
Beautiful place to stay! Very peaceful. Loved the carriage house.
Guest favourite
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 favourite
Home in Hallowell
4.98 out of 5 average rating, 130 reviews

Hilltop Retreat with Hot Tub & Sauna near Downtown

AshleyRating, 5 stars6 days ago
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.
Top Guest favourite
Home in Bridgton
5 out of 5 average rating, 104 reviews

Wren Cabin + Wood fired Sauna

CourtneyRating, 5 stars1 week ago
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.
Guest favourite
Home in Augusta
4.96 out of 5 average rating, 157 reviews

Lakefront: Private Hot Tub, Sauna & Free Massages!

MichelleRating, 5 stars5 days ago
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 favourite
Home in Lisbon
4.94 out of 5 average rating, 429 reviews

Unplug at a Beachy Bolthole with Classic New England Style

MatthewRating, 5 stars6 days 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.
Top Guest favourite
Home in Canton
4.99 out of 5 average rating, 154 reviews

Private Lakehouse, Firepit & Amazing Sunset Views

JaneRating, 5 stars2 weeks ago
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

Top Guest favourite
Apartment in Boothbay
4.97 out of 5 average rating, 323 reviews

Sunnymeade

SamanthaRating, 5 stars1 week 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 favourite
Apartment in Hallowell
4.95 out of 5 average rating, 310 reviews

High End Apartment in Downtown Hallowell

DaveRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Wilton
4.93 out of 5 average rating, 265 reviews

Apt above Ambition Brewing in Downtown Wilton

AmyRating, 5 stars1 week ago
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
Guest favourite
Apartment in Pittsfield
4.89 out of 5 average rating, 100 reviews

Loft Retreat

MarkRating, 5 stars2 weeks ago
This Airbnb was exactly as listed. Everything is updated, very clean, and comfortable. Jordana was very responsive and accommodating. I would stay here again.
Top Guest favourite
Apartment in Nobleboro
4.92 out of 5 average rating, 184 reviews

Finding Joy

VallerieRating, 5 stars3 days ago
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.
Top Guest favourite
Apartment in Gardiner
4.97 out of 5 average rating, 114 reviews

The Escape on Elm

NicoleRating, 5 stars4 days ago
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.
Top Guest favourite
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! ❤️
Top Guest favourite
Apartment in Bath
4.97 out of 5 average rating, 102 reviews

1820s Maine Cottage with Garden

RebeccaRating, 5 stars2 weeks ago
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

Guest favourite
Condo in Carrabassett Valley
4.95 out of 5 average rating, 133 reviews

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

DougRating, 5 stars3 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 favourite
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 favourite
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 favourite
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
Condo in Brunswick
4.85 out of 5 average rating, 180 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

BonnieRating, 5 stars3 weeks ago
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.
Top Guest favourite
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 favourite
Condo in Greenwood
4.98 out of 5 average rating, 43 reviews

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

JanetteRating, 5 stars5 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 favourite
Condo in Carrabassett Valley
4.96 out of 5 average rating, 91 reviews

First Tracks at Sugarloaf

RichardRating, 5 stars4 days ago
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

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