Kid-friendly holiday rentals in Oakland

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Oakland family-friendly rentals

Kid-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.
Top guest favourite
Home in Oakland
4.94 out of 5 average rating, 72 reviews

Classy AF Home, walk across the street to Colby!

JessicaRating, 5 stars1 week ago
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!
Guest favourite
Home in Northport
4.98 out of 5 average rating, 169 reviews

Cute Midcoast Cottage w Hot Tub

DustinRating, 5 stars1 week ago
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
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 Wayne
4.94 out of 5 average rating, 213 reviews

Peaceful Getaway at The Ledges

JeffreyRating, 5 stars8 months ago
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
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.

Family-friendly apartment rentals

Guest favourite
Flat in Damariscotta
4.92 out of 5 average rating, 286 reviews

Fernald's Backside

KriyaRating, 5 stars1 month ago
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!
Top guest favourite
Flat 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
Flat 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.
Guest favourite
Flat in Kingfield
4.96 out of 5 average rating, 363 reviews

On The River 2 with Lucy the resident cat

IsaahRating, 5 stars3 weeks ago
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
Top guest favourite
Flat 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
Flat 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
Flat 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! ❤️
Guest favourite
Flat in Augusta
4.82 out of 5 average rating, 117 reviews

Downtown Augusta - 2 Bedroom - Newly renovated!

TheodoraRating, 5 stars6 days ago
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

Guest favourite
Apartment in Hanover
4.87 out of 5 average rating, 63 reviews

6 miles from Sunday River with heated outdoor pool

CarmineRating, 5 stars3 months ago
Easy quick getaway for ski/snowboard trip
Guest favourite
Apartment 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
Apartment in Bethel
4.9 out of 5 average rating, 39 reviews

Riverbend Ski Condo < 3 miles to Sunday River

Emma CRating, 5 stars3 months ago
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.
Guest favourite
Apartment 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
Apartment 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
Apartment 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
Apartment 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
Apartment 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

    $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