Holiday 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 FLX Retreat | 200' Seneca Lakefront | Pool

Charming lakefront retreat on Seneca Lake’s northwest shore, ideal for families or friends. The main home offers five bedrooms, 2.5 baths, a spacious living area, and a fully equipped kitchen. Enjoy stunning lake views from the deck, an outdoor kitchen with grill, a seasonal pool, and a private shale beach. Minutes from downtown Geneva, wineries, breweries, and restaurants. A second SEASONAL cottage (Mid May-October) sleeps two and includes a full bathroom—perfect for added privacy.

The Fitz Farmhouse on West Lake.

It’s Summer!! Don’t miss out on a great stay with your friends or family at the Fitz Farmhouse! A professionally managed and cleaned home. The Fitz Farmhouse offers 5 bedrooms, 2.5 baths and a NEW spacious family room. Heated pool, spacious patio for entertaining and a classic wrap-around front porch with views of Canandaigua lake. Just minutes away from great hiking trails, wineries and downtown Canandaigua, where you can experience excellent restaurants and of course Lake Life.

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.

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.

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.

Historic Lakeview Home w/ Pool & Hot Tub

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.

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.