Vacation rentals with a pool in Ontario County

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!"

Pool & Hot Tub+Gameroom+Movieroom+Firepit+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. 💦 Hot Tub (year-round) + In-ground Pool (seasonal - open Memorial - Labor Day) 👨‍🍳 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

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.

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.

Hotel Canandaigua Lakefront Condo - Pool/Hot Tub

Luxurious condo at Hotel Canandaigua: Enjoy pool, seasonal hot tub (opens in May) complimentary docking, and proximity to Kershaw Park. Features modern kitchen, cozy sitting area, plush bedrooms with balcony, 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 🍴

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.

Charming Lakeview House w/ Pool & Fire Pit

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.

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!

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.

South West Cottage: Cozy Getaway, King Beds, Pool

South West Vineyard Cottage — a bright, farmhouse-style 1912 home in Geneva’s Founders Square, steps from Hobart & William Smith. Relax in 4 king bedrooms, enjoy central air, a full kitchen, fast Wi-Fi, and a private in-ground pool (open Apr 15–Oct 1). Close to Seneca Lake, downtown, and Finger Lakes wineries. Dog-friendly — perfect for families, groups, and wine-country getaways.

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.

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!