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 Woodstock
4.91 out of 5 average rating, 209 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Sep 20 – 27
Home in Cottekill
4.95 out of 5 average rating, 241 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Sep 9 – 16
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 Woodstock
4.85 out of 5 average rating, 191 reviewsHeated Pool/Private: Woodstock Mediterranean
Aug 12 – 19
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
Home in Woodstock
4.92 out of 5 average rating, 154 reviewsWoodstock Home Close to 3 Towns, Hiking and More
May 4 – 11
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio with Pool & Mountain Views
Jul 15 – 22
Condo rentals with a pool
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
Aug 28 – Sep 4
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
May 15 – 22
Condo in Windham
4.95 out of 5 average rating, 22 reviewsLovely stylish 2-bedroom condo with community pool
May 28 – Jun 4
Condo in East Jewett
4.97 out of 5 average rating, 94 reviewsMountain&PondView2BRCondoFireplace
May 25 – Jun 1
Condo in Hunter
4.84 out of 5 average rating, 69 reviewsCozy Gem with Mountain Views
Jun 14 – 21
Condo in Hunter
4.93 out of 5 average rating, 27 reviewsCozy Mt. Getaway/community pool!
Aug 1 – 8
Condo in East Jewett
4.95 out of 5 average rating, 22 reviewsHunter & Windham: Ski, Hike, 2BR + Mountain View
Jul 6 – 13
Condo in Hunter
4.91 out of 5 average rating, 47 reviewsHunter Mtn Slopeside Ski Resort w HotTub*Fireplace
Jul 31 – Aug 7
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep 23 – 30
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Apr 18 – 25
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Nov 28 – Dec 5
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Sep 25 – Oct 2
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Aug 25 – Sep 1
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 7 – 14
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
€ 65 before taxes and fees
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