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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakland family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Searsport
4.82 out of 5 average rating, 293 reviewsLakefront Vacation Apartment in Searsport ME
Cabin in Appleton
4.88 out of 5 average rating, 278 reviewsRaven's Crossing - Kate's Cottage
Chalet in Carrabassett Valley
4.98 out of 5 average rating, 114 reviewsHot tub! Outdoor paradise! PAC-MAN!
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
Cottage in Chesterville
4.73 out of 5 average rating, 66 reviewsPrivate Lakefront Getaway in Central Maine
Cabin in Chesterville
4.86 out of 5 average rating, 43 reviewsLakefront Log Cabin-boats-fishing-swimming-hot tub
Guest suite in Lincolnville
4.95 out of 5 average rating, 44 reviewsWaterfront Loft w/ Bold Ocean Views
Guest suite in Carrabassett Valley
4.95 out of 5 average rating, 21 reviewsSugarloaf Mountain Village Lodging
Family- and pet-friendly home rentals
Cabin in Dresden
4.96 out of 5 average rating, 157 reviewsMcKeen's Riverside Retreat
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
Apartment in Edgecomb
4.91 out of 5 average rating, 299 reviewsSunny Apt in Woods 10 Min to 3 Towns- Dog Friendly
Cabin in Montville
4.83 out of 5 average rating, 107 reviewsCozy Off-Grid Cabin on Organic Farm and Homestead
Cabin in Carthage
4.94 out of 5 average rating, 182 reviewsPrivate Maine Camp
Home in Stetson
4.96 out of 5 average rating, 151 reviewsLakefront Log Cabin on Pleasant Lake
Island in Monmouth
4.98 out of 5 average rating, 195 reviewsIsland Glamping in a Luxury Tent in Maine
Guest suite in Union
4.83 out of 5 average rating, 134 reviewsFarmhouse Suite w/ Private Entrance—Midcoast
Family-friendly home rentals with a pool
Apartment in Cornville
4.85 out of 5 average rating, 123 reviewsLarge Home with Great View next to horse farm
Cottage in Belfast
4.58 out of 5 average rating, 12 reviewsShore Cottage
Home in Carrabassett Valley
4.82 out of 5 average rating, 62 reviewsSUGARLOAF, TRAILSIDE, 4-BDRM, & AC
Home in South Thomaston
4.95 out of 5 average rating, 83 reviewsLarge private area, close to Rockland
Home in Peru
4.95 out of 5 average rating, 210 reviewsthe lake house
Condo in Carrabassett Valley
4.95 out of 5 average rating, 44 reviewsCozy Ski In, Ski Out End Unit Condo
Cottage in Poland
4.59 out of 5 average rating, 17 reviewsLake Beach House at Poland Spring Resort
Home in Benton
5.0 out of 5 average rating, 13 reviewsRiverside home in Central Maine near Colleges
Quick stats about vacation rentals that are family-friendly in Oakland
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
770 reviews
Nightly prices starting at
€ 102 before taxes and fees
Destinations to explore
- Portland Vacation rentals
- Bar Harbor Vacation rentals
- Old Orchard Beach Vacation rentals
- Ogunquit Vacation rentals
- Bangor Vacation rentals
- Wells Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Moncton Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Maine
- Family-friendly rentals Maine
- Family-friendly rentals Portland
- Family-friendly rentals Bar Harbor
- Monthly Rentals Oakland
- Rentals with outdoor seating Oakland
- Rentals with a kayak Oakland
- House rentals Oakland
- Rentals with a washer and dryer Oakland
- Kid-friendly rentals Oakland
- Rentals with lake access Oakland
- Rentals with a fire pit Oakland
- Rentals with a patio Oakland
- Waterfront rentals Oakland
- Rentals with a fireplace Oakland
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom