Family-friendly vacation 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.
Vacation 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
Apartment in Stone Ridge
4.94 out of 5 average rating, 271 reviewsStone Ridge Historic District Apartment
Jul 22 – 29
Home in Olivebridge
4.92 out of 5 average rating, 428 reviewsFamily Catskills Getaway Cabin with Hot Tub
Sep 11 – 18
Cottage in Phoenicia
4.89 out of 5 average rating, 800 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Jun 21 – 28
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
Oct 3 – 10
Home in woodstock
4.86 out of 5 average rating, 486 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Aug 13 – 20
Home in Bearsville
4.92 out of 5 average rating, 191 reviewsA Cozy’s Woodstock Getaway Home
May 16 – 23
Home in Woodstock
4.94 out of 5 average rating, 880 reviews1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole
Jun 8 – 15
Home in Neversink
4.98 out of 5 average rating, 200 reviewsModern Riverside Retreat with Firepit, Hot tub
Feb 10 – 17
Family- and pet-friendly home rentals
Farm stay in High Falls
4.87 out of 5 average rating, 808 reviewsDave's Milk Barn
Oct 26 – Nov 2
Barn in Woodstock
4.84 out of 5 average rating, 166 reviewsThe Woodstock Barn Studio
Jun 24 – Jul 1
Cabin in Boiceville
4.94 out of 5 average rating, 214 reviewsCatskills Mountain River Dream House
Apr 16 – 23
Cabin in Kerhonkson
4.94 out of 5 average rating, 177 reviewsThe Laurel Cabin
Jun 29 – Jul 6
Home in Accord
4.97 out of 5 average rating, 116 reviewsLittle Minka - Woodland Japanese Cabin.
Jul 5 – 12
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
Aug 16 – 23
Home in Stone Ridge
4.95 out of 5 average rating, 121 reviewsSecluded Contempo w Fireplace in Stone Ridge
Sep 15 – 22
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 8 – 15
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
May 6 – 13
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
May 17 – 24
Guest suite in New Paltz
4.84 out of 5 average rating, 181 reviewsPrivate apartment in rural home
Jan 17 – 24
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 21 – 28
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
Nov 26 – Dec 3
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Oct 27 – Nov 3
Home in Woodstock
4.88 out of 5 average rating, 139 reviewsShula | Modern Farmhouse | Pool, Hot tub, Fire pit
Feb 1 – 8
Cabin in Livingston Manor
4.96 out of 5 average rating, 257 reviewsExperience The Zen House
Feb 18 – 25
Quick stats about vacation 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
€ 56 before taxes and fees
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