Family-friendly holiday rentals in Windham
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham
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 Windham family-friendly rentals
Family-friendly home rentals with a hot tub
Guest suite in South Portland
5.0 out of 5 average rating, 683 reviewsOceanfront with amazing views and private entrance
19 – 26 Oct
Home in Waterford
4.83 out of 5 average rating, 217 reviewsMcWain pond house (private lake & hot tub)
10 – 17 Mar
Treehouse in Georgetown
4.98 out of 5 average rating, 404 reviewsModern Tree Dwelling w/Water Views+Cedar Hot Tub
14 – 21 Dec
Apartment in Topsham
4.87 out of 5 average rating, 498 reviewsMaine Stay with private hottub, near Brunswick
17 – 24 Aug
Apartment in Biddeford
4.98 out of 5 average rating, 118 reviewsBrenda and Phil's Place
26 Sept – 3 Oct
Cottage in Conway
4.89 out of 5 average rating, 295 reviewsHOT TUB! Amazing view. Hike, Bike, Swim!
31 July – 7 Aug
Cabin in Rochester
4.94 out of 5 average rating, 216 reviewsawesome private cabin
16 – 23 Apr
Tiny home in Harrison
4.9 out of 5 average rating, 280 reviewsMILLION$ views, HOT TUB, Crooked RIVER, 14 acres
25 Dec – 1 Jan
Family- and pet-friendly home rentals
Apartment in Lisbon falls
4.95 out of 5 average rating, 383 reviewsCharming Victorian farmhouse 1880's bedrooms-2
8 – 15 Apr
Cabin in Windham
4.91 out of 5 average rating, 193 reviewsPrivate Hilltop Cabin, Lakes and Trails Abound..
27 June – 4 July
Farm stay in Scarborough
4.85 out of 5 average rating, 214 reviews434 Acres and a Cabin
9 – 16 Dec
Apartment in Harpswell
4.83 out of 5 average rating, 240 reviewsSunny Apartment on the Ocean.
11 – 18 Mar
Home in Paris
4.94 out of 5 average rating, 129 reviewsJust a get away!!
18 – 25 Dec
Cottage in Gray
4.9 out of 5 average rating, 190 reviewsSunset Haven - Little Sebago Lake
25 Feb – 4 Mar
Guest suite in Freeport
4.96 out of 5 average rating, 186 reviewsWaterfront Private Apartment just 5 min to LL Bean
6 – 13 Jan
Barn in Naples
4.85 out of 5 average rating, 172 reviewsPeace on High, Entire home throughout your stay!
24 Apr – 1 May
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
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
2 – 9 Oct
Condo in Bartlett
4.72 out of 5 average rating, 201 reviewsExcellent Getaway in N.Conway area!
2 – 9 Mar
Condo in Intervale
4.93 out of 5 average rating, 147 reviewsUpscale retreat w/ panoramic White Mountain views
22 – 29 Sept
Chalet in Bartlett
4.92 out of 5 average rating, 170 reviews*Summit Vista 2Bd2Br|Ski Chalet|N.Conway&Shopping
4 – 11 Aug
Home in Kennebunk
4.81 out of 5 average rating, 114 reviewsKennebunk/Kennebunkport Beach House w/Pool!
17 – 24 Feb
Apartment in Bartlett
4.78 out of 5 average rating, 125 reviewsGround Floor Getaway for Two!
12 – 19 Aug
Condo in Bartlett
4.95 out of 5 average rating, 175 reviews★Spacious, Updated, Beautiful Condo @ The Seasons★
16 – 23 May
Quick stats about holiday rentals that are family-friendly in Windham
Total rentals
130 properties
Wi-Fi availability
120 properties include access to Wi-Fi
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Total number of reviews
4.2K reviews
Nightly prices starting at
$138 AUD before taxes and fees
Destinations to explore
- Portland Holiday rentals
- Salem Holiday rentals
- Chebacco Lake Accommodation & holiday rentals
- Old Orchard Beach Holiday rentals
- Lake Winnipesaukee Accommodation & holiday rentals
- Jersey City Holiday rentals
- New York Accommodation & holiday rentals
- The Hamptons Holiday rentals
- Boston Accommodation & holiday rentals
- Montreal Accommodation & holiday rentals
- Québec City Accommodation & holiday rentals
- Québec Accommodation & holiday rentals
- Family-friendly rentals United States
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- Family-friendly rentals Portland
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