
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

Livingston Manor Retreat

Shaggerties - fun cozy catskill mountain getaway

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View

1800’s Rosendale Cottage with pool

The Crooked Cottage

Spacious Private Retreat w. Pool + Fireplace

Upstate Modern Scandinavian Barn in the Catskills

Heated Saltwater Pool/Hot Tub/Kid Friendly!
Apartment rentals with a pool

Cozy Gem with Mountain Views

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Windham Condo

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

Luxury 3-bedroom Condo on Windham mountain

Hunter & Windham: Hikes, Lakes, Swimming, 2BR

Luxury Ski in Ski out Condo + Amenities

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym
Quick stats about holiday rentals with a pool in Olive
Total rentals
30 properties
Nightly prices starting at
$192 SGD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Rentals with a fireplace Olive
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Belleayre Mountain Ski Center
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Thunder Ridge Ski Area
- Taconic State Park
- Zoom Flume
- Hudson Highlands State Park
- Bash Bish Falls State Park
- Walkway Over the Hudson State Historic Park
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Mohawk Mountain Ski Area
- Villa Roma Ski Resort
- Opus 40
- Mount Peter Ski Area
- Hunter Mountain Resort
- Bull's Bridge Golf Club
- Plattekill Mountain