Vacation rentals with a pool in Canandaigua

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Canandaigua

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The interior of the A-frame features high wooden ceilings and an open layout. A spacious seating area is arranged with a large sofa and matching chairs, while a dining table sits beneath decorative wall art. A staircase leads to a lofted sleeping area with a railing.

Home in Newfield

4.97 out of 5 average rating, 181 reviews

Camp S’mores- Modern A-Frame with Pool

Welcome to Camp S’mores- this revitalized luxury A-frame has all the modern amenities you need for your Finger Lakes adventure. We just brought new life into this house from top to bottom. The home features three bedrooms and a Murphy bed in the game room on the lower level. EV charger. It wouldn't be camp without a pool so our home has a large HEATED in-ground pool is open May 15th - Oct 1st. The house is located outside of town on 2+ private acres. Dog friendly, sorry no cats or other pets

Guest favorite

An indoor swimming pool area is seen, featuring a clear blue pool with tile borders. Lounge chairs are arranged along the sides, and windows allow natural light to brighten the space. Beams of dark wood support the vaulted ceiling, contributing to a spacious feel.

Home in Pittsford

4.86 out of 5 average rating, 120 reviews

Charming Pittsford Home-Indoor Pool-4 bedrooms

My home is in the Bushnell's Basin/Perinton part of Pittsford. .5 miles to 490, 4 mi to I-90 and 15 minutes to U of R. Erie Canal is a short walk away. The 17 mi Crescent Trail head is 100 yards away. Fantastic restaurants. The large indoor pool is open year round with new filter and pool heater. A stream is in the fenced backyard. 50 trees provide privacy and shade. The 4 bedrooms are spacious and 21/2 baths ensure no waiting! 2 decks. Golf, Finger Lakes, wineries, & breweries are close.

Top guest favorite

A spacious wooden deck is presented, featuring a circular above-ground pool surrounded by greenery. A shaded area is provided by a red umbrella over a dining table. Soft evening light filters through the trees, enhancing the serene outdoor space.

Apartment in Seneca Falls

5 out of 5 average rating, 129 reviews

Luxury lakefront apartment - and a pool!

This new apartment on Cayuga Lake is in the middle of New York's famous Finger Lakes. Seneca Falls is a quaint, quiet community surrounded by dozens of wineries, trails, parks, boating, fishing and more - a vacation paradise, and home to the National Women's Hall of Fame. Your private deck overlooks the lake, plus there's a private pool, deck and grill. 2 bedrooms, full tiled bath, huge modern kitchen, and hi-def TVs in the living room and bedrooms w/free Netflix, Prime Video, Hulu & Disney+.

Guest favorite

An in-ground pool is seen with clear blue water, surrounded by a stone patio. White lounge chairs are positioned along the edge, inviting relaxation. The pool features a shallow entry area with steps leading into the water, enhancing access for all guests.

Home in Canandaigua

4.92 out of 5 average rating, 109 reviews

Perfect secluded ski house, lake views, 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!"

Top guest favorite

A spacious bedroom features a large window providing natural light and a view of greenery. A cozy bed is positioned near a decorative fireplace, with calming white walls and minimal decor. A vintage-style dresser sits against the wall, enhancing the room's serene atmosphere.

Apartment in Auburn

4.94 out of 5 average rating, 137 reviews

Heart of Historic Finger Lakes! Fireplace, balcony

Kick back and relax in this calm, stylish space. Perfect for a romantic getaway or work retreat, this recently renovated apartment embodies a fresh boho feel with vintage soul. Enjoy the beautiful view out the large picture window, cooking in the adorable and functional kitchenette, or relaxing in bed by the gas fireplace. Located in Auburn's historic district and a 1-min. drive from Wegmans. From here you can easily access downtown shops, restaurants, and attractions by foot.

Top guest favorite

A bright living area features a spacious gray sofa paired with a comfortable armchair. A decorative coffee table sits atop a light area rug, and a wall-mounted TV is visible opposite the seating. Natural light fills the room through large windows, enhancing the wood flooring.

Home in Elmira

4.95 out of 5 average rating, 110 reviews

Comfy Ranch House 3BR/2BA with Pool

Welcome to our cozy Upstate NY retreat! Perfect for traveling workers or family vacations, this newly renovated 3-bedroom, 2-bathroom house offers a comfortable stay. It features a stocked kitchen, laundry room, and spacious, furnished rooms. In the summer, enjoy our 24-foot round pool with a deck and lounge chairs. The backyard has a 5-burner gas grill, a gliding bench, and an outdoor table with a retractable umbrella, ideal for dining and relaxing. Book now for a great stay!

Superhost

An aerial view of Villa Vino reveals a spacious property with a large house featuring a wide porch. The backyard includes a fenced seasonal pool covered for the off-season, surrounded by landscaped gardens and expansive green lawns, bordered by trees in autumn colors.

Villa in Keuka Park

4.9 out of 5 average rating, 125 reviews

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.

Superhost

An in-ground swimming pool is framed by lush greenery, featuring clear blue water and a gently sloping entry. The surrounding concrete deck is well-maintained, with space for lounging. A diving board is positioned at the far end, offering an inviting spot for summer fun.

Home in Penfield

4.83 out of 5 average rating, 169 reviews

Penfield-Webster Home w/Pool - Park Like Setting

Charming 19th century 2,300 sq.ft. farmhouse with 3 large bedrooms on 1 acre. Stately coffer ceiling in expansive living room. Recently update with refinished floors, paint and new kitchen appliances. Inviting breakfast room with french doors leading to side yard. Private 1+ acre yard with 18'x38' in-ground pool on park like setting directly across from Town Park. 5 minutes to shopping and entertainment and a short 15 min. drive to downtown Rochester.

Top guest favorite

An above-ground pool is surrounded by a concrete patio, bordered by lush greenery. A staircase leads up to the pool area, which features lounge chairs in bright colors. The pool is covered partially, indicating seasonal use.

Guest suite in Rochester

4.99 out of 5 average rating, 352 reviews

Private Guest Suite/RIT-UofR-airport

Well equipped charming guest suite with a private entrance on the ground level with pool access. Conveniently located to many locale attractions. Our place is in a small neighborhood ( 72 homes) with side walks. The Rochester airport is East of us and about three miles away, Robert Wesleyan, RIT, and U of R are about five miles away. WE DO NOT HOST GUEST THAT LIVE LOCALLY. You can always inquire for special request or situations for exceptions.

Guest favorite

An outdoor space features a spacious in-ground pool surrounded by a white fence. Several lounge chairs in vibrant colors are positioned around the pool, complemented by a round dining table with four chairs. Lush greenery is visible in the background.

Home in Lima

4.96 out of 5 average rating, 161 reviews

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.

Guest favorite

A serene swimming pool is surrounded by a stone patio, with lounge chairs positioned nearby. Lush greenery provides a natural border around the pool area. A pot of red flowers adds a touch of color to the scene, completing the inviting outdoor space.

Apartment in Ithaca

4.9 out of 5 average rating, 221 reviews

Private apartment with full kitchen (dog friendly)

This apartment is located in the basement of a family home. It is a self-contained private unit with a separate entrance, full kitchen, bathroom with shower and washer/dryer and a living space. The property is fenced and has a pool for use in the summer and a pond with fish to feed. Friendly dogs are welcome (the owners have a friendly beagle-basset who loves to meet other dogs). Please note that we have ducks who free range in the yard.

Top guest favorite

A serene pool is framed by a grassy area and lush greenery, with clear blue water reflecting sunlight. Metal steps lead into the pool, and a portion of the pool deck remains shaded, offering a peaceful setting for relaxation.

Home in Fairport

4.99 out of 5 average rating, 178 reviews

Esten-Wahl Farm - Historic Landmark Victorian Home

The farm is 30 acres of pasture, woods and a stream - peaceful, yet within a bike ride to the village of Fairport and the Erie Canal. There is a small cottage hidden behind the historic barn where we live and care for the animals on the farm. Our guests' privacy is paramount and the farm is yours to wander and enjoy (including the pool and tennis court) as you wish! The pool is open mid-May through Mid-September.