Holiday rentals with a pool in Ontario County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ontario County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Guest house in Canandaigua

4.5 out of 5 average rating, 6 reviews

The Juniper at Bristol Woodlands

Relax in this sleeping cabin with bath facilities steps from your door. The cabin is inside a seasonal campground and includes all amenities of the campground. On-site are 4 walking trails, a swimming pool, camp store, 2 bath houses and activities for all. Inside the cabin you'll find air-conditioning, a mini fridge, a microwave and a Keurig for your morning coffee. You'll also have your own deck, fire pit and picnic table.*There is no running water inside the cabin and linens are not provided*

Guest favourite

Home in Canandaigua

4.92 out of 5 average rating, 101 reviews

Perfect secluded ski house, lake views, hot tub

Secluded, spacious home, overlooking Canandaigua Lake on 6 wooded and park-like acres. Breath-taking Panoramic views. Surrounded by forest and bordering a winding gully for year-round hiking. In-ground pool, 4-season hot tub on enormous deck; lovely glamping tent in woods with natural fire-pit. Gas grill and chef's kitchen for after a long day of skiing at Bristol Mountain, 12 miles away. Full gym. Wine / beer-tours, boating, golf, nature, right outside. Relax and enjoy this "Chosen Spot!"

Guest favourite

Home in Penn Yan

5 out of 5 average rating, 24 reviews

Lakeview, Pool + HotTub l PuttPutt | Gamerm | Dog OK

Bring the whole family to Keuka Playhouse, our 5BR/3BA 2-story home on the Keuka Wine Trail w/views of the lake. 💦 In-ground Pool (seasonal - open Memorial - Labor Day) + Hot Tub (year-round) 👨‍🍳 Gas grill 🔥 Outdoor Fire pit + Indoor Fireplace ⛳️ Putt Putt Golf + Gameroom 🎬 Theater Room ⚡️ EV Charging 🐶 Dogs OK (max 2) 🍷 Short drive to Penn Yan Village, public lake access & wineries The perfect place for large groups to unwind & enjoy the Finger Lakes ❤️ us to find us next time

Superhost

Home in Canandaigua

5 out of 5 average rating, 4 reviews

Finger Lakes Chalets Farmhouse Annex- Pool Open!

Take it easy at this unique and tranquil getaway. A super spacious FOUR room comfortable and cozy getaway with swimming pool (seasonal) awaits at this characterful 1880’s Homestead on 14 peaceful acres. Close to an array of amenities/attractions in Canandaigua and Naples, lake access just down the hill. Thoughtfully apportioned annex to provide an ENTIRELY DEDICATED 2- Person fully functioning stay. Complete with a Kitchenette, dedicated fire pit,& barbeque picnic area.

Top guest favourite

Barn in Bloomfield

4.97 out of 5 average rating, 59 reviews

The Green House

Get away from it all when you stay under the stars at this beautiful farm situated on 80 acres of rolling farmland, hills and forests, with horses, chickens and Nigerian Dwarf goats. Walk out the sliding glass door to a fully fenced pool and hot tub overlooking the beautiful rolling hills and woods. We live right next to the Green House. The Famous Finger Lake Wineries and Breweries are a short drive away. We are also 20 minutes away from Bristol Mountain Ski Resort.

Superhost

Villa in Keuka Park

4.89 out of 5 average rating, 119 reviews

Villa Vino - Outstanding 4bd home w/Hot Tub & Pool

Welcome to Villa Vino. Family fun and adventure await at this outstanding home located in a quiet neighborhood perched atop the hills above Keuka Lake. This beautiful and tastefully decorated sanctuary provides the ideal location for your next vacation. Complete with a year-round Hot Tub & seasonal in-ground pool, billiard table and firepit. The whole group will be comfortable in this spacious and unique space. Conveniently located next door to Esperanza Mansion.

Guest favourite

Apartment in Canandaigua

4.94 out of 5 average rating, 31 reviews

NEW Condo | Hot Tub | Pool | Restaurant | FLX

Luxurious condo at Hotel Canandaigua: Enjoy pool, hot tub, complimentary docking, and proximity to Kershaw Park. Features modern kitchen, cozy sitting area, plush bedrooms, wrap around balcony with lake views, spa-like bathroom, and high-speed internet. Near breweries, wineries, and live music. Perfect Finger Lakes getaway! 🌟🏊🛥️🍷🎵📺 1 Min Walk - Kershaw Park 🏖️ 2 Min Drive - CMAC Preforming Arts Center🎵 5 Min Drive - Canandaigua Strip 🍴

Guest favourite

Home in Lima

4.96 out of 5 average rating, 154 reviews

pool, theater room, & fully equipped kitchen

Enjoy this newly renovated home nestled in a private cul-de-sac with the town park with playground and walking trails literally in your back yard. Lots to do to have fun—swim in the in-ground pool, make teams for a foosball tournament, gather around the table to play board games, watch a movie in the theater room, or snuggle up by the fire and enjoy a quiet night in. Cook meals in the fully equipped kitchen or on the grill on the back patio.

Guest favourite

Home in Geneva

5 out of 5 average rating, 6 reviews

Lakeview on Main • Pool, Fire Pit + Walkable

Step into timeless charm at Lakeview on Main—your private escape in the heart of historic downtown. This grand home features a pool, fire pit, and partial lake views, plus four bedrooms, 2.5 baths, and a private office for work or creativity. With stylish outdoor living spaces, original architectural details, and modern updates throughout, it’s the perfect setting for family vacations, friend getaways, or a mix of productivity and play.

Top guest favourite

Home in Geneva

5 out of 5 average rating, 6 reviews

Raise Your Glass Ranch

Raise Your Glass Ranch is close to so many wineries, breweries and the best restaurants the area has to offer. Check out my guidebook! This property also offers amazing peace, privacy, and plenty of space. Perfect for your bachelorette/bachelor party or family gathering. It’s a great place to let your hair down and raise your glass! NEW! An EV car charging option is available for an additional charge.

Guest favourite

Chalet in Canandaigua

4.92 out of 5 average rating, 61 reviews

Inspiring A-FRAME:Panoramic Lake Views & Hot Tub!

The Serene, Peaceful setting is a perfect getaway for a couple, a Family or Friends to meet up and reconnect. Enjoy beautiful panoramic Sunrise or Sunset views from the multiple decks, take a dip in the pool or brand NEW Hot tub, go exploring in the wooded back drop or create a cozy night around the fire pit! This is a place where memories are made!

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Popular amenities for Ontario County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Naples

4.8 out of 5 average rating, 85 reviews

6 Acres w/ Pool: Spacious Naples Vacation Rental!

GiyooRating, 5 stars1 month ago

Loved staying at Mary’s place. Beautiful surroundings, peaceful and private. Beds were comfy, water was hot, lots of space for the 9 people in our party and kitchen was stocked with many amenities and the host was kind enough to leave us a special treat on our arrival. There was a small water issue but the host came over to get it fixed on a Sunday which our group very much appreciated. We had a lovely stay at their beautiful home, thank you Mary and Ed!

Guest favourite

Home in Canandaigua

4.87 out of 5 average rating, 31 reviews

1920's Farmhouse- Antique Charm Abounds

SyrenaRating, 5 stars2 days ago

If you’re thinking about booking PA’s Place, I highly recommend staying here! Lovely location, convenient and accessible to the highway, shopping, and the wedding venue we attended. It’s a welcoming home with everything we needed. Kate was great! It was a busy weekend and thankfully our stay was easy and stress-free. Very down to earth family-friendly hosts. Our family (dogs included) felt right at home. The location is clean, safe, dog-friendly, has plenty of parking right near the entrance, and reliable hosts who are easy to communicate with. The hosts even left a few thoughtful treats!

Guest favourite