Holiday rentals with a pool in Ontario County

Lakeview, Pool+HotTub l PuttPutt | Gamerm | Dog 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

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.

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.

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 🍴

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.

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.

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.

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!

FLX Farmhouse - Close to Wineries & Breweries

Located on nearly 7 acres, our home offers inspiring views of the Finger Lakes hills, walking trails, and privacy! You'll get the peaceful, country setting along with the high speed wifi and city amenities you're accustomed to.