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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Guest favourite

A private balcony offers stunning views of Canandaigua Lake, with expansive greenery and walking paths visible below. A single chair provides a space to relax and enjoy the serene surroundings, while the distant shoreline blends with the sky in soft hues.

Apartment in Canandaigua

4.81 out of 5 average rating, 26 reviews

NEW Lakeview Escape | Hot Tub | Poolside

Luxurious condo at Hotel Canandaigua: Enjoy pool, hot tub, complimentary docking, and proximity to Kershaw Park. Features modern kitchen, cozy sitting area, plush bedrooms, balcony with lake views, spa-like bathroom, and high-speed internet. Near breweries, wineries, and live music. Perfect Finger Lakes getaway! 🌟🏊 ******NOTE**** Each guest will have only 1 key fob for the condo. We recommend using the lock box and coordinating properly with you group. 🚫 There's NO Washer & Dryer in the unit

Guest favourite

An aerial view showcases a one-level home surrounded by a spacious grassy yard. The in-ground pool is visible alongside the backyard features, including a swing set and a four-hole putt-putt golf course. Keuka Lake and its scenic shoreline can be seen in the background.

Home in Penn Yan

5 out of 5 average rating, 11 reviews

3N+ Promo! Lakeview | HotTub+Gameroom| Dog+EV OK

Cozy one-level 3 BR/2 BA home (sleeps 6) located on the Keuka Lake Wine Trail & offering views of Keuka Lake. A short drive to Penn Yan Village & public lake access. • Hot Tub (year-round) + In-ground Pool (seasonal - currently closed until Memorial Day 2025) • Deck w/gas grill • Firepit and Seating w/lake views • Gameroom • Putt Putt Golf • Fireplace • EV Charging • Dogs OK (max 2) The perfect place for friends & family to unwind & enjoy the Finger Lakes! <3 us to find us easily next time!

Guest favourite

A spacious home is set within a lush, wooded landscape, showcasing rich autumn colors. The structure features large windows, providing natural light, and is framed by verdant trees and shrubs. An expansive lawn extends in front, inviting outdoor activities.

Home in Canandaigua

4.92 out of 5 average rating, 113 reviews

Foster Hideaway - lake views, pool, 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!"

Top guest favourite

A modern living area is presented with a sleek brown leather sofa and a light wood coffee table positioned on a soft area rug. A large flat-screen TV is mounted on the wall opposite a decorative console. Natural light fills the room through a glass door leading to an outdoor space.

Flat in Canandaigua

5 out of 5 average rating, 20 reviews

Relaxation, Unwind and Enjoy #508

Welcome to our breathtaking condo nestled along the serene shores of Canandaigua Lake. This idyllic retreat offers a perfect blend of tranquility, modern comforts, and natural beauty, providing you with an unforgettable vacation. With its prime location on the lake and a myriad of amenities, this condo offers the perfect blend of relaxation and adventure. Whether you're seeking a romantic getaway or a solo retreat, this picturesque oasis promises an unforgettable vacation experience.

Top guest favourite

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

4.97 out of 5 average rating, 38 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!

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.

Chalet in Canandaigua

5 out of 5 average rating, 8 reviews

Finger Lakes Chalets Farmhouse Annex

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.

Guest favourite

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

4.95 out of 5 average rating, 81 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 favourite

A spacious property is set on a green lawn, bordered by trees with autumn foliage. The house features a sloping roof and a driveway leading towards the lake, which is visible in the background. The landscape showcases a serene view of the waters and surrounding hills.

Villa in Keuka Park

4.88 out of 5 average rating, 133 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

The living room features two comfortable leather sofas positioned across from each other, centered around a circular coffee table. A gas fireplace with a stone surround is visible, complemented by a wall-mounted TV above it. Natural light fills the space through large windows.

Home in Lima

4.96 out of 5 average rating, 170 reviews

Fireplace, 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.

Top guest favourite

The exterior of the grand home is showcased, featuring a green facade with inviting architectural details. A spacious porch wraps around the front, framed by neatly trimmed bushes and trees, providing a serene atmosphere. The home's varied rooflines and large windows enhance its classic charm.

Home in Geneva

5 out of 5 average rating, 17 reviews

Lakeview on Main Pool, Fire Pit and 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, 4 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 favourite

A private rectangular pool is surrounded by a sleek gray concrete patio and secured with a black metal fence. A water slide curves into the pool, while lounge chairs are arranged nearby. Lush green trees provide a natural backdrop.

Home in Bloomfield

5 out of 5 average rating, 78 reviews

2 Bedroom pool house with Garage

Make some memories at this unique and family-friendly place. Peaceful location that is close to Rochester and Canandaigua as well as Bristol Mountain for skiing or viewing foliage. Tranquility at your fingertips. The pool is generally open from Memorial weekend until Labor day weekend. The last day the pool will be heated for 2025 is September 27th.