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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Guest favourite

Home in Palermo

5 out of 5 average rating, 9 reviews

Serenity on Sheepscot Lake

Bring the whole family (or two) to our lake in mid coast Maine! This year round home is in a peaceful setting yet close to coastal towns of Belfast and Camden. Enjoy a paddle around the lake with our kayaks, canoe or simply hang out on the dock. The clean lake is an angler’s dream. We are set up for the youngest (crib, toys, swings)to the oldest ( one step into first floor, bedroom directly across from bathroom). Fall and winter stays bring even more quiet and respite from the outside world.

Guest favourite

Home in Carrabassett Valley

4.92 out of 5 average rating, 37 reviews

A Perfect Home For Family Summer Vacations!

This expansive and family-oriented home is situated on Sugarloaf, offering 5 bedrooms, 4.5 bathrooms, two spacious living areas, and a generously sized kitchen and dining space. Located on the Winter shuttle route and within close proximity to hiking/biking trails, the Carrabassett River and golf course! Enjoy the gas fireplace after a day on the slopes or a game of ping pong with the family! Nestled in the mountains, this exquisite home presents an ideal setting for your upcoming vacation.

Superhost

Home in Windham

4.7 out of 5 average rating, 67 reviews

The "Happy Hen House" cottage in lakes region

Choose to stay here! The cottage is close to restaurants, shopping, arcades, miniature golf & swimming. Stay in this cozy classic cottage that includes 2 semi-private bedrooms (no doors), one with a queen size bed, the other with twin size bunk beds. On the main level, enjoy the sofa that opens to a full size bed; feel free to cook in the kitchen which is equipped w/stove, refrigerator, microwave, toaster & coffee maker. There is also a grill on the back deck w/plenty of outdoor seating.

Guest favourite

Home in Naples

4.95 out of 5 average rating, 104 reviews

Paradise in the Lakes Region

A spectacular, massive, state-of-the-art log cabin that's the perfect getaway for summer vacations (beaches, water-sports, cookouts, galore), fall gatherings (stunning scenery) & winter ski trips (only 25 minutes to Pleasant Mountain) with friends or family. With a chef's kitchen, two ovens, a large dining area, bedrooms for up to 12 (with two king beds), two living rooms, & tons of outdoor dining & relaxation space, there's no gathering this wonderful, warm, gorgeous home can't accommodate!

Guest favourite

Cabin in Greenwood

4.92 out of 5 average rating, 13 reviews

All seasons Lake House next to ski areas

Welcome to the Howell’s cabin ! A beautiful and peaceful lake house in the heart of Maine. Located just 5 minutes from Mt Abrahm ‘s ski area , 20 minutes from Sunday River Ski Center, and 15 minutes from Bethel, a charmy town with great restaurants and unique attractions. This has been our family getaway for nearly 40 years. Recently renovated, fully equipped kitchen, tiled bathroom, heating/ AC system, Wi-Fi and a nice deck to enjoy your morning coffee. No suitable for infants under 6

Guest favourite

Home in Camden

4.87 out of 5 average rating, 15 reviews

Cozy Cottage - Close to Downtown Camden!

Relax with the whole family at this cozy cottage nestled between downtown Camden and Megunticook Lake. Enjoy your morning coffee on the porch with a peaceful setting. We recently renovated to provide more privacy for guests traveling as two couples or w/families. We pride ourselves in creating a level of hospitality that may often be overlooked. If you leave an item or two behind, we likely have you covered for basic amenities, you will truly get lost in the comfort of this little cottage!

Superhost

Chalet in Woodstock

4.95 out of 5 average rating, 86 reviews

On Lake Christopher, Close to Sunday River

Cozy chalet right on Lake Christopher (aka Bryant Pond), 15 mins to Bethel, 20 mins to Sunday River, 12 mins to Mt Abram, 30 mins to Grafton Notch State Park, 1 hour 15 mins to Portland. Clear swimming water, surrounded by excellent hiking, skiing/snowboarding/XC skiing, hunting, fishing, rock climbing, kayaking, more! Kid friendly (we have toddler essentials), but not kid-proof (please use your parental discretion!) Kayaks/SUP board included with rental. July/Aug: Weekly Sat to Sat only.

Top guest favourite

Guest house in Belfast

4.98 out of 5 average rating, 51 reviews

Adorable cottage 5 minute walk from downtown

Newly custom renovated 1 BR, 2 floor cottage 5 minute walk from downtown, 2 minutes from farmers market & bay. Each floor has a balcony for AM coffee/evening drinks. Loft style master BR connecting bathroom, first floor kitchen/living room combo - full (compact) kitchen - Custom woodwork, great design. Bathroom accessible from 2nd Fl BR. (The couch was recently replaced it’s not the one pictured (it’s actually much more comfortable) Crib available upon request No pets No smoking

Guest favourite

Cottage in Northport

4.88 out of 5 average rating, 16 reviews

Charming and Rustic Cottage, water and park view

This is a charming and rustic cottage in the village of Bayside. If you're new to Bayside, consider it the land that time forgot. Adorable little seaside village of Victorian cottages. Walking distance to the 9 hole golf course, or the park with small playground and basketball court. Safe and so family friendly. Enjoy gorgeous views of the wharf and bay. Perfect for family with kids. Short drive to Belfast and Camden, where you will find plenty of good food and activities.

Superhost

Home in Greenwood

4.97 out of 5 average rating, 109 reviews

Lakeside getaway for 6 by Sunday River!

Located along Main Street, this beautifully restored lake front home had a private dock and yard facing the lake. Come enjoy summer on the lake with our canoes, kayaks and corn hole. In the winter come to ice skate in the front yard and ski at Sunday River (20mins) or Mt Abrams (5mins). House offers high speed internet, a smart TV and modern amenities. Custom dining nook, custom kitchen and modern, yet cozy finishes throughout.