
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
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Popular amenities for Olive rentals with a pool
House rentals with a pool

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
Our stay at Susanna’s was perfect! We have zero complaints. Had everything we needed and more! We would definitely stay there again when in the area!

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Harrison Field Pool Bike2Town FirePit 10AcreViews
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

Upstate Modern Scandinavian Barn in the Catskills
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Modern House with Private Pool, Hot-Tub, Fireplace
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
This property is beautiful! The house and amenities are actually just as nice in real and every detail was so thought out. Arp really has good taste and communicated well throughout our stay.

Upstate Mountain Cottage
Our hosts have curated a beautiful and thoughtful space, with pleasing personal details, design and decor that made our stay easy, relaxed and met all of our needs for a quick get-away from city life…wood burning stoves for the fire-gazers, a well-outfitted kitchen for those of us who sought to cook as meditation, a crop of woods for kids to explore, a bilingual library for our bilingual readers etc. that rounded out the feasting of a holiday of Thanksgiving around the dining table. The house is near good food shopping, retail and restaurant culture etc. and could cause one to want to spend more time than a mere get-away in order to take it all in as well as enjoy the house itself; hence, we will have to plan to return-! Alex was incredibly responsive; the stove is beautiful, though somewhat enigmatic with its icons, and she offered to take time on her own holiday to walk us through it—and with one or two other minor questions she was patient and quick to reply. Merci Bien!
Condo rentals with a pool

Cozy Gem with Mountain Views
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.

Windham Condo
We had an amazing stay at Kristen’s condo with our family—my husband, our toddler, and our dog. The location was perfect—secluded and peaceful, but still close to hiking trails and charming small towns. The condo was cozy, clean, and well-equipped with everything we needed for a relaxing weekend. Kristen was responsive and helpful, making our stay even better. Highly recommend for a family getaway!

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub
My family and I had a 2 night stay at Neil's place in June for a family wedding. The condo unit was spotless. Everything seemed very modern. We loved that each bedroom had an associated bathroom. Really a perfect place. Will be super convenient during ski season!

Hunter & Windham: Hikes, Lakes, Swimming, 2BR
My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.

4 Bedroom Condo, Close to Golf Courses and Biking
Very nice place with decent pricing. lots of room, clean, good communication from host.

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym
We recently stayed at Andrew's condo, and it was nothing short of amazing! The location couldn't be better – right next to the slopes with easy accessibility to the mountain and the ski rental place. We were a group of two families, totaling 6 kids and 4 adults, and the condo was the perfect accommodation for our ski trip. The kids were thrilled with their bunkbed rooms, each equipped with their own TVs, providing a cozy and entertaining space for them to unwind after a day on the slopes. The condo itself was beautifully decorated, creating a warm and inviting atmosphere. There was plenty of room for all of us to relax and spend quality time together. The highlight for both kids and adults was undoubtedly the hot tub and pool. After a day of skiing, it was pure bliss to soak in the hot tub and enjoy the breathtaking views. A special shoutout to Andrew, our fantastic host! He was incredibly responsive and welcoming, ensuring that our stay was comfortable and stress-free.

Luxury Ski in Ski out Condo + Amenities
We worked through a bit of calendar scheduling snafu quickly. Scott was accommodating, proactive, and responsive. The condo was in a great location, maintained well, and clean. We very much enjoyed our quick weekend getaway. Thank you!

Summer Retreat w/ Balcony & inground Pool
Was as advertised. Would recommend
Quick stats about holiday rentals with a pool in Olive
Total rentals
30 properties
Nightly prices starting at
$232 AUD 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
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Opus 40
- Mount Peter Ski Area
- Bull's Bridge Golf Club
- Thaddeus Hait Farm
- Plattekill Mountain