Vacation rentals with a pool in Ontario County

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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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Guest favorite

An in-ground pool is seen with clear blue water, surrounded by a stone patio. White lounge chairs are positioned along the edge, inviting relaxation. The pool features a shallow entry area with steps leading into the water, enhancing access for all guests.

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!"

Superhost

An aerial view captures a spacious property with a large grassy yard, featuring an in-ground pool. Keuka Lake and lush greenery are visible in the background, with various home structures along the lakeside. The surrounding area is bordered by trees and showcases a peaceful landscape.

Home in Penn Yan

4.92 out of 5 average rating, 25 reviews

Lakeview + Pool + HotTub l PuttPutt | Gamers | Dogs 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

Guest favorite

An aerial view showcases the spacious layout of the chalet surrounded by lush greenery. The property features a unique curved stone wall, a large backyard, and a wraparound driveway, leading to the inviting entrance of the home. A private pool area can be seen on the side.

Home in Canandaigua

4.96 out of 5 average rating, 26 reviews

Mountain Views, Hot Tub, Spa, Fire Pit, Game Room

Welcome to Alpine Retreat, your ultimate dream destination nestled in the heart of the picturesque Finger Lakes region! This charming mountain side chalet offers the perfect blend of luxury, comfort, and breathtaking views, making it an ideal getaway for families and friends alike. Get ready for an unforgettable Finger Lakes vacation where every moment is filled with beauty, comfort, and cherished memories. Book your stay now and embrace the true essence of mountain side living!

Superhost

A clear swimming pool reflects sunlight, with gentle ripples across the water's surface. Surrounding the pool are lounge chairs and a shaded area with an umbrella. A rustic house stands in the background, framed by greenery and flowers.

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 favorite

A vast, open landscape features rolling hills and fields of green, under a clear blue sky. Sparse trees line the edges of the property, with a distant view of a white farm structure nestled among the greenery.

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.

Guest favorite

An aerial view of Villa Vino reveals a spacious property with a large house featuring a wide porch. The backyard includes a fenced seasonal pool covered for the off-season, surrounded by landscaped gardens and expansive green lawns, bordered by trees in autumn colors.

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 favorite

The image showcases a modern condo building with a sleek exterior design, featuring multiple balconies and large windows. In the foreground, a well-maintained swimming pool is visible, surrounded by a spacious patio area equipped with lounge chairs and landscaping for a relaxing atmosphere.

Condo in Canandaigua

4.94 out of 5 average rating, 32 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 favorite

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 favorite

An inviting swimming pool is framed by a wrought-iron fence, with lounge chairs and an umbrella providing shaded seating. A stone patio features a grill and cozy seating areas, surrounded by lush greenery and trees, creating a serene outdoor retreat.

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.

Superhost

An A-frame cabin is nestled among lush trees, featuring a welcoming wooden porch with two chairs. Soft lighting illuminates the entrance, emphasizing the cabin's unique architectural design against the tranquil forest backdrop.

Cabin in Canandaigua

5 out of 5 average rating, 3 reviews

Modern A-Frame Glamping | Nature + Comfort

Escape to our cozy A-frame glamping cabin—perfect for couples craving nature, comfort, and connection. Sip wine by your private firepit, relax in a plush queen bed, and explore nearby waterfalls, wineries, and Canandaigua Lake. Just 13 miles from CMAC for unforgettable date nights. Book your romantic getaway today in the Wildfire at Bristol Woodlands! Traveling with friends? We have 8 of these cabins onsite—perfect for groups!

Top guest favorite

A clear blue pool is surrounded by a spacious patio area, featuring a blue float and several loungers. A shaded seating area with a table and chairs is visible, along with the large farmhouse in the background. Lush greenery frames the serene outdoor space.

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 favorite

A spacious outdoor area features a heated in-ground pool surrounded by a white picket fence, with lush greenery in the background. An A-frame chalet is visible, highlighting multiple decks and an inviting landscape perfect for relaxation and recreation.

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!

Vacation rentals for every style

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A space thats all yours, with room for everyone

Popular amenities for Ontario County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view displays a charming property surrounded by lush greenery. A red barn with a spacious deck is visible alongside a two-story home. A private swimming pool is situated near the deck, set against a backdrop of trees and open lawn.

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 favorite

An above-ground pool is set on a spacious wooden deck, surrounded by green trees and open grass. Adirondack chairs are positioned on the deck, offering a relaxing space to enjoy the outdoors. A small shed is visible in the background, with an American flag gently waving.

Home in Canandaigua

4.87 out of 5 average rating, 31 reviews

1920's Farmhouse- Antique Charm Abounds

SyrenaRating, 5 stars1 week 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 favorite

An aerial view captures the enchanting log cabin set amid lush greenery. A sparkling pool is surrounded by a stone patio and seating, while a cozy fire pit area is visible nearby. The expansive lawn and natural wooded surroundings create a peaceful outdoor retreat.

Home in Springwater

4.92 out of 5 average rating, 52 reviews

Cabin Retreat | Hot Tub | Pool | Game Room | FLX

SheniquaRating, 5 stars2 days ago

Beautiful, spacious house with plenty of household items provided like pool towels, Kcups, and plenty of trash bags, paper towels, etc. Pool, hot tub, and game room kept kids and adults entertained the entire week. WiFi/cell service isn’t great, especially on the pool deck/porch/patio areas which wasn’t necessarily a bad thing to disconnect during our stay. TV in upstairs master bedroom didn’t work enough to actually watch it (turns on but freezes repeatedly, remote worked off and on etc) We definitely WANT to book this house again but would need confirmation that the A/C is more dependable/consistent as the downstairs bedroom/bathroom were FREEZING COLD while all the other bedrooms were hot and uncomfortable (and the weather was only in the 60s/70s during our stay). Vibe was very responsive and came to assist with pool the next day when there was a concern. Staff was very friendly and proactive overall. ⭐️⭐️⭐️⭐️