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
Home in Olivebridge
4.92 out of 5 average rating, 432 reviewsFamily Catskills Getaway Cabin with Hot Tub
Home in woodstock
4.86 out of 5 average rating, 487 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Cottage in Phoenicia
4.89 out of 5 average rating, 808 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
Home in Bearsville
4.92 out of 5 average rating, 192 reviewsA Cozy’s Woodstock Getaway Home
Home in Mount Tremper
4.91 out of 5 average rating, 200 reviewsStunning Modern Barn minutes from Woodstock 21N195
Home in Highland
4.96 out of 5 average rating, 111 reviewsHouse in Highland: Secluded Retreat
Apartment in New Paltz
4.96 out of 5 average rating, 469 reviewsRelaxing Spa Retreat~Gorgeous View~Walk to Village
Family- and pet-friendly home rentals
Cabin in Kerhonkson
4.94 out of 5 average rating, 179 reviewsThe Laurel Cabin
Cabin in Boiceville
4.94 out of 5 average rating, 214 reviewsCatskills Mountain River Dream House
Home in Stone Ridge
4.95 out of 5 average rating, 121 reviewsSecluded Oasis w/ Screened Porch In Stone Ridge
Cottage in Kerhonkson
4.89 out of 5 average rating, 451 reviewsMod Scandinavian! HudsonValley!tiny Flower Farm
Home in Accord
4.97 out of 5 average rating, 117 reviewsLittle Minka - Woodland Japanese Cabin.
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
Home in Kerhonkson
4.94 out of 5 average rating, 326 reviewsCountry House: Rustic Charm With Modern Feel
Cabin in Kingston
4.87 out of 5 average rating, 626 reviewsCharming cabin. Catskills. Secluded on 11 acres.
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
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Cabin in Red Hook
4.96 out of 5 average rating, 308 reviewsModern Upstate Cabin, near Rhinebeck NY
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Home in Woodstock
4.89 out of 5 average rating, 160 reviewsSecluded 7acres, Saline Heated Pool, Spa, Stream !
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
$60 before taxes and fees
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