Vacation rentals with a pool in Yates County

6 BR house w/ hot tub, fireplace + dog friendly

Escape to the charming town of Dundee, NY, where this delightful house awaits you for a memorable getaway. Perfectly designed for families and pet lovers alike, this dog-friendly retreat offers a cozy atmosphere with modern amenities. Relax in the private above-ground pool on warm summer days, unwind in the hot tub after a day of exploring, or gather around the firepit on the patio for an evening under the stars. The spacious living room features a gas fireplace and a sofa bed, ensuring comfort

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Pool + HotTub, Game room, Fire pit | Dogs+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 2026) • 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!

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

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Sky House- private sanctuary in the clouds

Float among the clouds at Sky House, where a crackling wood stove and sweeping views of Keuka Lake will leave you feeling at peace and in awe. Sky House is perfect for special celebrations, romantic getaways, personal creative retreats, or a WFH change of scenery. We are located on the Bluff with 20 acres over looking the west side of the lake. Just five minutes from Keuka Lake State Park! We’re so excited to share this slice of heaven with you! *Four wheel drive needed for winter months*

Tranquil Airstream Nature Escape

Escape to the Finger Lakes and experience the charm of Airstream living! Our Airstream Bambi is a peaceful retreat designed for relaxation, adventure, and reconnecting with nature. Spend your days sipping coffee by the fire pit, enjoying your own pool exclusively for Airstream guests, exploring local wineries, or stargazing beneath the trees. This unique stay offers the perfect blend of comfort, simplicity, and outdoor living. Perfect for nature lovers and pet-friendly too!

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Modern Lakeside Villa with Pool and Hot Tub

Introducing Esprit Bleu, a newly built and designed lakeside villa vacation home in the heart of Keuka Lake Finger Lakes wine country, situated on 20 private acres of uncut meadow. 5 day minimum July/Aug The home features 3 bedrooms downstairs and an open floor plan upstairs with views of the adjacent vineyard and just a 5 minute drive to Keuka Lake. Pet friendly An inground heated pool May-Oct and hot tub highlight this home that stuns all year. Pets permitted.

NEW! Family-friendly home along Seneca Lake

Gather with your friends and family in our welcoming ranch-style home located along the West side of Seneca Lake. This inviting getaway offers you and your family the perfect starting base for all of your adventures in the beautiful Finger Lakes region of New York. Whether you are looking to explore nature in nearby Watkins Glen (10 mins) or enjoy a tasting at one of the area’s signatures wineries or breweries, this home offers you the ideal location.

Norris View

Norris View is a one‑of‑a‑kind hillside retreat designed to give you space, comfort, and complete relaxation. Built directly into the hill, this thoughtfully designed home naturally stays cool during the summer—enjoy fresh air through open windows with gently circulating fans, even on warm days. Whether you’re looking to spend sunny days lounging by the pool, exploring nearby trails, or enjoying cozy nights filled with laughter and relaxation.

Finger Lakes Home w/ Private Pool & Lake Views!

Private Acreage | 8 Mi to Champlin Beach (Keuka Lake) | Fire Pit Immerse yourself in an unparalleled escape at this 3-bedroom, 2-bath vacation rental situated in the heart of Hammondsport wine country! This vacation rental features an updated interior complete with everything you need for a perfect getaway. Voted ‘Coolest Small Town in America,’ Hammondsport offers incredible scenery and wines, year-round outdoor fun, and holiday markets!

Lakefront Cottage | Pet Friendly | Fire Pit | Pool

Private cottage on Seneca Lake with a fenced yard, fire pit, and access to hotel amenities—offering the perfect mix of seclusion and convenience. Ideal for couples, wine weekends, or a quiet getaway. Enjoy lake access, relax by the fire, and explore nearby wineries. Dog-friendly with rare private outdoor space, all set on a peaceful 9-acre waterfront property.

Valley View | Poolside Retreat | Hot Tub/Game Room

Surrounded by 30 private acres in the Naples countryside, this spacious Finger Lakes home accommodates up to 18 guests with an ensuite bathroom in every bedroom. Enjoy Italy Valley views, a seasonal in-ground pool, hot tub, game room, and generous gathering spaces near Hi Tor, Canandaigua Lake, wineries, and downtown Naples.