Vacation rentals with a pool in Prince Edward

An aerial view captures the property featuring a heated pool surrounded by a wooden deck. The house has a spacious layout with outdoor seating nearby. Lush green lawns and mature trees frame the area, with fields and a road visible in the background.

5 out of 5 average rating, 50 reviews

Pearadise on West Lake | Waterfront w/ Pool

Newly renovated family-friendly 4 bedroom house on 2 acre property on West Lake with small pear orchard and heated pool (open mid-May to mid-Sept). Centrally located between Wellington and Bloomfield, the property is steps from Wellington Farmer's Market (every Sat May to Oct), events at the Eddie and Wander Resort. Waterfront with a dock, large lawn with a play structure, waterside pergola with 12ft picnic table, large pool deck with dining and lounge seating and sweeping lake views throughout.

Bungalow in Prince Edward

A spacious outdoor area is shown, featuring a large pool surrounded by loungers and a dining set. Lush greenery is visible in the background, with blue skies and sunlight creating a bright atmosphere. The scene invites relaxation and outdoor gatherings.

4.98 out of 5 average rating, 107 reviews

Beautiful Relaxing Getaway With Sauna&Private Pool

WOODLANDS If you are looking for total privacy in the heart of the County, you have found it! Woodlands offers you almost 4 acres of land, beautiful bungalow with 2000sq feet of living space upstairs, 2000sq feet of a walkout basement, and a large outdoor pool. Please inquire about pets prior to booking. Only non shedding dogs up to 40 lbs are allowed. Please note that the pet fee applies to each pet. We do not accept cats due to allergies.Thank you for your understanding STA LIC ST-022-0160

An aerial view captures a spacious backyard featuring a modern heated pool surrounded by lounge chairs. A fire pit seating area is placed nearby, with the backdrop of trees and a vibrant sunset sky illuminating the scene. The contemporary back of the house faces the pool.

4.97 out of 5 average rating, 162 reviews

Prince Edward Landing

Victorian Home in PEC gets a full renovation to become a one of a kind vacation home. Featured in the Globe & Mail the house is a 2018 restoration of old-world charms with as many contemporary comforts as one wishes. From the gorgeous landscape and a screened-in, white-trim front porch to the fully modern spectacular interior The back of the house is a stunning starkly contemporary black box, designed by architect Jay Pooley, a lecturer at the University of Toronto’s school of architecture.

Bungalow in Prince Edward

An above-ground pool is surrounded by a wooden deck featuring colorful lounge chairs in green and orange. Two inflatable pool floats, a unicorn and a flamingo, rest on the water's surface. Lush greenery is visible in the background, providing a serene atmosphere.

4.88 out of 5 average rating, 100 reviews

Harwood House

AirBnB: "Your listing is one of the top." A charming three bedroom home on a quiet street at the edge of Wellington. Just inches outside the hubbub of Ontario's most popular summer destination! Steps away from everything. Near the LCBO, Lakeshore Farms Market, Wellington Bakery. A few more minutes and you're on main street Welli with an array of fine dining and nightlife. You're in the epicentre of Wine Country, within minutes of dozens of name-brand wineries, breweries, marvelous attractions.

4.96 out of 5 average rating, 56 reviews

A charming cottage is shown with light green siding under a clear blue sky. The structure features a covered solarium with a mesh enclosure, surrounded by well-maintained grass and a small tree, adding a touch of greenery.

Cottage in Prince Edward

Unique 2 Bedroom Resort Cottage in Prince Edward

Experience a cottage in a Resort setting minutes from Sandbanks beach! It's a perfect getaway for beachgoers, wine lovers, and families looking to create precious memories. Our cottage sits on a shared 80acre resort which includes 2 heated pools, a fitness center, basketball courts, tennis courts, putting green, a children's playground, and much more. Minutes from the town of Picton with countless shops and restaurants. Come and experience the beauty of Prince Edward County! Cheers! Riz&Eshan

4.94 out of 5 average rating, 248 reviews

The cottage is situated along the shoreline of Consecon Lake, surrounded by lush greenery. A spacious deck extends from the cottage, offering access to a seasonal dock. A pool is visible on the deck, enhancing the outdoor space along the water.

Cottage in Consecon

Lakefront Cottage with Pool, Hot Tub & Sauna

Welcome to your Prince Edward County getaway! Our Muskoka-style lakefront cottage with pool, sauna and hot tub was custom-built in 2004. Perfect for families and very private, it comfortably sleeps 8 adults with additional room for children (10 years and under). Located literally on the edge of Consecon Lake, we're 13 mins from Wellington & close to over a dozen wineries. We've been Superhosts since 2017, and our family would love to host you and welcome you to our little slice of paradise.

An outdoor pool is framed by lush greenery and a rustic wooden barn. Two lounge chairs with umbrellas provide shaded seating, and a well-maintained grassy area surrounds the pool, creating a peaceful space for relaxation.

4.95 out of 5 average rating, 199 reviews

The Old Stone Farmhouse with Hot Tub & Heated Pool

Renovated historic stone farmhouse located about 6km from both Picton and Bloomfield. Relax in the hot tub, swim in the pool, lay in the hammock or enjoy a campfire under the stars. Over 2 acres of beautiful country views to explore. However, we are still close enough to the action that you can get to Bloomfield, Picton or some of the biggest wineries by bike. Ideal for couples and small group getaways. Hot tub is operational year round. Pool is open beginning of June - end of September.

A backyard oasis features a glistening in-ground pool surrounded by lush greenery. Tall trees cast gentle shadows, while the sun rises in the sky, illuminating the serene outdoor space. The grassy area invites relaxation and enjoyment during warmer months.

4.96 out of 5 average rating, 57 reviews

** The Cherry Valley House **

Welcome to The Cherry Valley House! This beautiful century old historic home has been recently renovated to provide the latest in contemporary amenities while retaining all of the old world charm that attracts one to the county. The home is within short driving distance to Picton, Bloomfield, Sandbanks Provincial Park and the many wineries, restaurants and breweries ! We look forward to hosting our guests and having them experience all that is so wonderful about Prince Edward County!

An inviting in-ground pool is set within a spacious patio area, surrounded by lush greenery. Several loungers are arranged nearby, complementing a shaded seating area with chairs. Inflatable floaties rest in the water, enhancing a relaxed atmosphere for outdoor enjoyment.

5 out of 5 average rating, 25 reviews

Marina and Main - In Ground Pool and Games Room

Discover the ultimate getaway in Wellington, Prince Edward County. This stylish 3-bedroom, 2.5-bathroom home features a stunning backyard with an in-ground pool—perfect for summer relaxation. The separate carriage house (seasonally open between May 16 and September 30th) is an entertainment haven with a movie projector, ping pong table, and arcade games. Located in the heart of Prince Edward County, you're just minutes from wineries, beaches, and top dining. Your perfect escape awaits!

A serene outdoor space features a newly installed inground pool surrounded by lush greenery. Light-colored stone pavers create a clean border around the pool, while two loungers are positioned nearby for relaxation. A garden shed is visible in the background.

5 out of 5 average rating, 33 reviews

Evermore Guest House

*Pool closes Sept 29th . Sauna remains open !* This beautifully renovated 3 bedroom century home features a rustic bohemian style to bring out the natural artistic beauty of the County. Located just off Picton's Main St, this home will have everything you need within a few minutes walk. After exploring all that the County offers, unwind at home on your large back deck with new inground pool. We look forward to hosting you and making sure that you have the perfect getaway !

The outdoor pool area features a 30-foot heated salt-water pool surrounded by lounge chairs and umbrellas. This inviting space is bordered by lush greenery, offering a serene setting for relaxation and enjoyment during warm days.

4.94 out of 5 average rating, 197 reviews

Dragonfield House: a beautiful stay in central PEC

Dragonfield House: STA License No. ST-2024-0206 Featured in Canadian House and Home, March 2015, Dragonfield House was designed with a contemporary approach to country living. It is a four bedroom split-level country house, plus a guest yoga retreat with all the amenities of a city home. It features a heated salt-water pool (Mid May until Mid October) and a brand new year round hot tub for six people! There are three work/desk areas within the house ideal for remote working.