Family-friendly holiday 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.
Holiday 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
23 Feb – 2 Mar
Cabin in Appleton
4.88 out of 5 average rating, 277 reviewsRaven's Crossing - Kate's Cottage
31 Mar – 7 Apr
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
3–10 Jun
Chalet in Carrabassett Valley
4.98 out of 5 average rating, 114 reviewsHot tub! Outdoor paradise! PAC-MAN!
14–21 Sep
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
5–12 Sep
Loft in Andover
4.98 out of 5 average rating, 154 reviewsPrivate studio loft, decks and hot tub
18–25 Apr
Cottage in Verona Island
4.88 out of 5 average rating, 154 reviewsNashport on the Penobscot
23–30 Oct
Home in Newry
4.96 out of 5 average rating, 109 reviewsThe Ridge House-Modern Chalet! Spectacular Views!
26 Nov – 3 Dec
Family- and pet-friendly home rentals
Cabin in China
4.89 out of 5 average rating, 161 reviewsRustic Family Cabin on China Lake
Apartment in Lisbon falls
4.95 out of 5 average rating, 383 reviewsCharming Victorian farmhouse 1880's bedrooms-2
27 Apr – 4 May
Apartment in Edgecomb
4.91 out of 5 average rating, 298 reviewsSunny Apt in Woods 10 Min to 3 Towns- Dog Friendly
25 Jan – 1 Feb
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
26 Dec – 2 Jan
Cabin in Boothbay
4.93 out of 5 average rating, 179 reviewsPeaceful & private waterfront cabin
23–30 Oct
Farm stay in Gray
4.94 out of 5 average rating, 249 reviewsGreat Goat Get-away in Southern Maine!
22–29 Jan
Home in Stetson
4.96 out of 5 average rating, 151 reviewsLakefront Log Cabin on Pleasant Lake
6–13 Jan
Cabin in Montville
4.83 out of 5 average rating, 107 reviewsCozy Off-Grid Cabin on Organic Farm and Homestead
20–27 Jul
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
7–14 Aug
Apartment in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
26 Oct – 2 Nov
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
2–9 Mar
Chalet in Rangeley
4.86 out of 5 average rating, 159 reviewsA+ Views 2 Relax Write Hike Fish Boat Sunset/Stars
31 Dec – 7 Jan
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
23–30 Aug
Condo in Newry
4.94 out of 5 average rating, 101 reviewsSunday River Resort Condos @Cascades
15–22 May
Chalet in Frye Island
4.76 out of 5 average rating, 82 reviewsCabin in Paradise
17–24 Aug
Cottage in Belfast
4.58 out of 5 average rating, 12 reviewsShore Cottage
14–21 Apr
Quick stats about holiday rentals that are family-friendly in Oakland
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
$183 NZD before taxes and fees
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