Family-friendly vacation rentals in Oakland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oakland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Nov 19 – 26

ﺩ.ﺇ568 per night

Guest favorite

Cabin in Weld

4.97 out of 5 average rating, 156 reviews

Colby's Cabin

Beautiful, off-the-grid, rustic log cabin on 10 acres one mile up a 4-wheel drive trail. Located in a wilderness region minutes to Webb Lake, Tumbledown Mountain & Mt. Blue State Park. Trails of all kinds right out the front door. In the middle of Maine’s finest hiking, hunting, fishing, and boating. A perfect place for adventure, romance, celebration or serenity. An escape from the electronic world, the cabin has solar and battery lights but no power generator. (See Winter Conditions below)

Dec 23 – 30

ﺩ.ﺇ324 per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Jul 14 – 21

ﺩ.ﺇ571 per night

Guest favorite

Cabin in Skowhegan

4.82 out of 5 average rating, 401 reviews

The Cabin -Skowhegan

This guest house, main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler bed. Loft contains 2 twin beds. There is also a couch that could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large toaster oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/blu ray player, Gas BBQ (May to November 1st.), as well as a picnic table, with benches and an out door fire pit and wood is supplied.

Mar 21 – 28

ﺩ.ﺇ395 per night

Guest favorite

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Our cottage is meant to be both contemporary and rustic. It is where we go to get away from the hustle and bustle of the modern world and slow down. There is no TV or internet, even our phone is an old rotary one. You will see that we have a good radio, and games and books to read, and plenty of things to do outside. We hope you will take the time at our cottage to comfortably reconnect with yourself, and each other, while enjoying what Maine is renowned for, our quality of life

Apr 8 – 15

ﺩ.ﺇ513 per night

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 404 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Dec 14 – 21

ﺩ.ﺇ1,244 per night

Guest favorite

Apartment in Farmington

5.0 out of 5 average rating, 209 reviews

Escape and Engage at Bray Barn Farm!

Spacious, quiet carriage house in the Western Maine foothills nestled between farmhouse and barn. 15 acres of gardens, meadows and woods. Great for meandering and wandering about, walking the labyrinth, resting in the shade garden and orchid, and visiting with the donkeys and goats. Sleeps five. Great for time with family and friends, as well as solitude. We gladly accept all persons 21 and older. We welcome children and infants. 4 miles north of Farmington towards Sugarloaf.

Oct 10 – 17

ﺩ.ﺇ502 per night

Guest favorite

Island in Monmouth

4.98 out of 5 average rating, 193 reviews

Island Glamping in a Luxury Tent in Maine

The Hemlock Haven tent overlooks Annabessacook Lake. Sleep comfortably, cook your favorite meals, nap in the hammock, bask in the glow of the fire or woodstove, listen to the calls of the loons, play on the rope swing, canoe or kayak the lake, and walk the trails of this 14 acre wooded island. We greet you at our dock on shore, ferry you and your gear to the island, and ease you into island-life until you are settled. Enjoy super clean, Superhost, Maine Guide hospitality.

Oct 28 – Nov 4

ﺩ.ﺇ284 per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 10 – 17

ﺩ.ﺇ302 per night

Guest favorite

Apartment in Waterville

4.99 out of 5 average rating, 151 reviews

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

Sep 4 – 11

ﺩ.ﺇ981 per night

Guest favorite

Loft in Sidney

4.88 out of 5 average rating, 112 reviews

Barn Loft with Lake Views & Access

The Barn Loft is a studio living space with views and access to Messalonskee Lake! The Barn Loft has access to our sandy beach and kayaks, as well as a dock. The space has a small fridge with separate freezer, toaster, microwave, gas BBQ grill outside, and an outdoor fire pit for all of your s'mores needs (s'mores bar included! :) ! We also provide gourmet Maine roasted coffee. Access to lake is just a few steps down the driveway.

Sep 3 – 10

ﺩ.ﺇ937 per night

Guest favorite

Cabin in Phillips

4.93 out of 5 average rating, 163 reviews

Stream-side mountain retreat

This attractively renovated camp in the High Peaks region of western Maine is the perfect place to get away and unplug. Surrounded by conservation land, the camp is airy and bright, with views opening onto woods and stream, and is well screened. Solar panels provide water and electricity. There's limited satellite internet service for emailing and texting, and sometimes phone through wifi, depending on your service provider.

Nov 3 – 10

ﺩ.ﺇ669 per night