Family-friendly holiday rentals in Cumberland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Cumberland
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 Cumberland family-friendly rentals
Family-friendly home rentals with a hot tub
Treehouse in Georgetown
4.98 out of 5 average rating, 404 reviewsModern Tree Dwelling w/Water Views+Cedar Hot Tub
14–21 Dec
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
10–17 Mar
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
17–24 Aug
Apartment in Falmouth
4.89 out of 5 average rating, 170 reviewsFalmouth 3br near Town landing
9–16 Sep
Apartment in Biddeford
4.98 out of 5 average rating, 118 reviewsBrenda and Phil's Place
26 Sep – 3 Oct
Home in Portland
4.96 out of 5 average rating, 186 reviewsPeaceful Oasis with Water Views and Hot Tub!
21–28 Nov
Cabin in Rochester
4.94 out of 5 average rating, 216 reviewsawesome private cabin
16–23 Apr
Home in Old Orchard Beach
4.96 out of 5 average rating, 111 reviewsLuxury Beach House Old Orchard Beach Maine
19–26 Jan
Family- and pet-friendly home rentals
Guest suite in Freeport
4.96 out of 5 average rating, 186 reviewsWaterfront Private Apartment just 5 min to LL Bean
8–15 Oct
Farm stay in Scarborough
4.85 out of 5 average rating, 214 reviews434 Acres and a Cabin
28 Dec – 4 Jan
Guest suite in Brunswick
4.93 out of 5 average rating, 315 reviewsArt House Gallery guest suite
24–31 Dec
Apartment in Portland
4.97 out of 5 average rating, 396 reviewsBright and cozy Munjoy Hill neighborhood apartment
11–18 Mar
Guesthouse in Portland
4.97 out of 5 average rating, 564 reviewsThe Carriage House at Libbytown
25 Mar – 1 Apr
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
18–25 Dec
Apartment in Orr's Island
4.91 out of 5 average rating, 109 reviewsShore House, Posey Unit - Ocean Front Property
29 Nov – 6 Dec
Home in Biddeford
4.97 out of 5 average rating, 381 reviewsPrivate, spacious, colorful, fun & unique space
2–9 Nov
Family-friendly home rentals with a pool
Apartment in Brunswick
4.99 out of 5 average rating, 194 reviewsCharming Saltwater Farm apartment
17–24 Nov
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
25 Dec – 1 Jan
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
1–8 Oct
Home in Kennebunk
4.81 out of 5 average rating, 114 reviewsKennebunk/Kennebunkport Beach House w/Pool!
17–24 Feb
Condo in Wells
4.84 out of 5 average rating, 145 reviewsNew Condo on the Wells/Ogunquit town-line
17–24 Apr
Chalet in Frye Island
4.76 out of 5 average rating, 82 reviewsCabin in Paradise
17–24 Aug
Apartment in Falmouth
4.96 out of 5 average rating, 85 reviewsPoolside Suite-Gateway to Portland
3–10 Oct
Apartment in Boothbay Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Condo on Water's Edge in Boothbay Harbor
24–31 Mar
Quick stats about holiday rentals that are family-friendly in Cumberland
Total rentals
450 properties
Wi-Fi availability
440 properties include access to Wi-Fi
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
160 properties allow pets
Total number of reviews
28K reviews
Destinations to explore
- Portland Holiday rentals
- Salem Holiday rentals
- Chebacco Lake Holiday rentals
- Old Orchard Beach Holiday rentals
- Lake Winnipesaukee Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Québec City Holiday rentals
- Québec Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Maine
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- Family-friendly rentals Portland
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- Rentals with beach access Cumberland
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