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, 430 reviewsFamily Catskills Getaway Cabin with Hot Tub
Sep 13 – 20
Apartment in Stone Ridge
4.94 out of 5 average rating, 272 reviewsStone Ridge Historic District Apartment
Jun 20 – 27
Cottage in Phoenicia
4.89 out of 5 average rating, 804 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Sep 27 – Oct 4
Cottage in West Hurley
4.94 out of 5 average rating, 251 reviewsWoodstock Carriage House HotTub FirePit Pool
Oct 12 – 19
Home in woodstock
4.86 out of 5 average rating, 486 reviewsCABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN
Mar 23 – 30
Home in Bearsville
4.92 out of 5 average rating, 192 reviewsA Cozy’s Woodstock Getaway Home
Jun 2 – 9
Home in Woodstock
4.94 out of 5 average rating, 883 reviews1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole
Jun 18 – 25
Guest suite in New Paltz
4.95 out of 5 average rating, 327 reviewsMajestic Studio with Shawangunk Mountain Views
Jun 3 – 10
Family- and pet-friendly home rentals
Cabin in Kingston
4.87 out of 5 average rating, 623 reviewsCharming cabin. Catskills. Secluded on 11 acres.
May 21 – 28
Cabin in Kerhonkson
4.94 out of 5 average rating, 179 reviewsThe Laurel Cabin
Jul 8 – 15
Home in Accord
4.97 out of 5 average rating, 116 reviewsLittle Minka - Woodland Japanese Cabin.
Oct 16 – 23
Home in Stone Ridge
4.95 out of 5 average rating, 121 reviewsSecluded Contempo w Fireplace in Stone Ridge
Jul 23 – 30
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 9 – 16
Apartment in High Falls
4.98 out of 5 average rating, 813 reviewsTHE GARRET/Hudson Valley Wonderful!
Jun 13 – 20
Cabin in Woodstock
4.93 out of 5 average rating, 618 reviewsByrdcliffe Artist Studio (27.1-1-70)
Dec 4 – 11
Tiny home in Shandaken
4.85 out of 5 average rating, 164 reviewsCute Cabin with Great Mountain Views
Jul 14 – 21
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 14 – 21
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Oct 8 – 15
Guest suite in New Paltz
4.84 out of 5 average rating, 181 reviewsPrivate apartment in rural home
Mar 19 – 26
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
May 30 – Jun 6
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Jul 17 – 24
Home in Woodstock
4.89 out of 5 average rating, 141 reviewsShula | Farmhouse Modern| Pool, Hot tub, Fire pit
Mar 18 – 25
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Sep 17 – 24
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
ﺩ.ﺇ220 before taxes and fees
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- Rentals with a patio Olive
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