Vacation rentals with a pool in Olive
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Olive
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool
Home in Cottekill
4.95 out of 5 average rating, 244 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Home in Woodstock
4.89 out of 5 average rating, 142 reviewsShula | Farmhouse Modern| Pool, Hot tub, Fire pit
Home in Woodstock
4.85 out of 5 average rating, 192 reviewsWoodstock Retreat: Heated Pool/Private/Walk 2 town
Home in Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Woodstock
4.89 out of 5 average rating, 160 reviewsSecluded 7acres, Saline Heated Pool, Spa, Stream !
Home in New Paltz
4.93 out of 5 average rating, 122 reviewsHarrison Field Book 2 In June and 3rd Night 50%Off
Condo rentals with a pool
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
Condo in Windham
4.95 out of 5 average rating, 22 reviewsLovely stylish 2-bedroom condo with community pool
Condo in East Jewett
4.97 out of 5 average rating, 93 reviewsMountainView2BRCondo/Deck/Fireplace
Condo in Hunter
4.84 out of 5 average rating, 69 reviewsCozy Gem with Mountain Views
Condo in Hunter
4.92 out of 5 average rating, 48 reviewsHunter Mtn Slopeside Ski Resort w HotTub*Fireplace
Condo in Danbury
4.67 out of 5 average rating, 12 reviewsQuaint spacious unit,A+ location
Condo in Hunter
4.93 out of 5 average rating, 27 reviewsCozy Mt. Getaway/community pool!
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Quick stats about vacation rentals with a pool in Olive
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.4K reviews
Nightly prices starting at
$70 before taxes and fees
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