Holiday 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.
Holiday 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, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
2–9 Oct
Home in Woodstock
4.85 out of 5 average rating, 191 reviewsHeated Pool/Private: Woodstock Mediterranean
24 Sep – 1 Oct
Home in Woodstock
4.89 out of 5 average rating, 140 reviewsShula | Farmhouse Modern| Pool, Hot tub, Fire pit
28 Oct – 4 Nov
Home in Woodstock
4.91 out of 5 average rating, 211 reviewsJapanese Teahouse & Onsen, outside shower, tennis
8–15 Dec
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
29 Dec – 5 Jan
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
20–27 Oct
Home in Woodstock
4.89 out of 5 average rating, 159 reviewsSecluded 7acres, Saline Heated Pool, Spa, Stream !
15–22 Sep
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio with Pool & Mountain Views
15–22 Jul
Condo rentals with a pool
Condo in Windham
4.74 out of 5 average rating, 243 reviewsSummer getaway w/Pool & Tennis Court
6–13 Jul
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
8–15 Aug
Condo in Windham
4.95 out of 5 average rating, 22 reviewsLovely stylish 2-bedroom condo with community pool
2–9 Aug
Condo in East Jewett
4.97 out of 5 average rating, 94 reviewsMountainView2BRCondo/Deck/Fireplace
28 May – 4 Jun
Condo in Hunter
4.84 out of 5 average rating, 69 reviewsCozy Gem with Mountain Views
5–12 May
Condo in Danbury
4.82 out of 5 average rating, 11 reviewsQuaint spacious unit,A+ location
2–9 Jul
Condo in Hunter
4.93 out of 5 average rating, 27 reviewsCozy Mt. Getaway/community pool!
7–14 Jul
Condo in Hunter
4.92 out of 5 average rating, 48 reviewsHunter Mtn Slopeside Ski Resort w HotTub*Fireplace
6–13 Aug
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
27 Sep – 4 Oct
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
1–8 Mar
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
13–20 Sep
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
31 Aug – 7 Sep
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
12–19 Mar
Quick stats about holiday 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
$117 NZD before taxes and fees
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