Family-friendly holiday rentals in Olive
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Olive
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 Olive family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Olivebridge
4.92 out of 5 average rating, 429 reviewsFamily Catskills Getaway Cabin with Hot Tub
13–20 Sep
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
7–14 Oct
Apartment in Stone Ridge
4.94 out of 5 average rating, 272 reviewsStone Ridge Historic District Apartment
20–27 Jun
Cottage in Phoenicia
4.89 out of 5 average rating, 801 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
27 Jul – 3 Aug
Home in woodstock
4.86 out of 5 average rating, 486 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
29 Apr – 6 May
Home in Bearsville
4.92 out of 5 average rating, 192 reviewsA Cozy’s Woodstock Getaway Home
29 May – 5 Jun
Home in Woodstock
4.94 out of 5 average rating, 882 reviews1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole
15–22 Oct
Home in Neversink
4.98 out of 5 average rating, 200 reviewsModern Riverside Retreat with Firepit, Hot tub
8–15 Jan
Family- and pet-friendly home rentals
Farm stay in High Falls
4.87 out of 5 average rating, 809 reviewsDave's Milk Barn
24 Feb – 3 Mar
Home in Accord
4.97 out of 5 average rating, 117 reviewsThe Woods House, 40 secluded acres & speedy wifi!
21–28 Dec
Cabin in Kerhonkson
4.94 out of 5 average rating, 178 reviewsThe Laurel Cabin
16–23 Jun
Home in Accord
4.97 out of 5 average rating, 116 reviewsLittle Minka - Woodland Japanese Cabin.
27 Jun – 4 Jul
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
22–29 Aug
Cabin in Woodstock
4.93 out of 5 average rating, 617 reviewsByrdcliffe Artist Studio (27.1-1-70)
3–10 Dec
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
17–24 Sep
Cabin in Jefferson
5.0 out of 5 average rating, 432 reviews"Far from the Madding Crowd" Cozy Cabin Retreat
8–15 Jun
Family-friendly home rentals with a pool
Townhouse in Hunter
4.91 out of 5 average rating, 136 reviewsSpring into a Dynamic Stay at an Ideal Hunter Home
22–29 May
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
4–11 Oct
Guest suite in New Paltz
4.84 out of 5 average rating, 181 reviewsPrivate apartment in rural home
27 Mar – 3 Apr
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
22–29 Sep
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
14–21 Jul
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
29 Dec – 5 Jan
Home in Woodstock
4.89 out of 5 average rating, 140 reviewsShula | Farmhouse Modern| Pool, Hot tub, Fire pit
28 Oct – 4 Nov
Cabin in Livingston Manor
4.96 out of 5 average rating, 257 reviewsExperience The Zen House
12–19 Feb
Quick stats about holiday rentals that are family-friendly in Olive
Total rentals
150 properties
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
80 properties allow pets
Total number of reviews
9.9K reviews
Nightly prices starting at
$101 NZD before taxes and fees
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- Rentals with a fireplace Olive
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