Vacation rentals with a pool in Ontario County

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. Deck replaced in Fall 2025.

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

Private Cabin Retreat- Hot Tub | Pool | Game Room

Experience the magic of the Finger Lakes at this enchanting log cabin. Relax in your private retreat featuring a sparkling pool (closes October 14), cozy fire pit, and starlit hot tub. The kitchen blends rustic charm with modern convenience, while the living room offers a stone hearth electric fireplace. Enjoy the game room and unwind in tranquil bedrooms. Pet-friendly 2 dogs with fee IMPORTANT NOTE: Due to unforeseen circumstances, the hot tub will be temporarily unavailable until spring.

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!

Condo on Canandaigua Lake #420

Renting this 2-bedroom condo on the lake is not just about securing a place to enjoy a vacation;it's about embracing a lifestyle that seamlessly integrates modern comforts with the tranquility of nature. From the well-appointed interior to the breathtaking views, every aspect of this lakeside retreat is crafted to provide a haven of relaxation and inspiration. It's more than a home; it's a retreat where the beauty of the lake becomes an integral part of your everyday life.

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.

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!

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.

Canandaigua View w/Pool, Hot Tub & Fast Wifi

Stylish home tucked away high in the Bristol Mountains with amazing views of Canandaigua Lake. Our home is a stylish place to stay and perfect for families and friends looking for a peaceful getaway, offering picturesque views of Canandaigua Lake. Set on 9 private acres, it has all the modern amenities, an open floor plan, inground pool, hot tub, and pool table.

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.