Vacation rentals with a pool in Simcoe County

Dome in Bradford West Gwillimbury

A spacious backyard is highlighted by a fenced swimming pool surrounded by lounge chairs. A well-maintained lawn features picnic tables and outdoor recreational areas, with trees in the background reflecting fall colors under a partly cloudy sky.

4.96 out of 5 average rating, 388 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.95 out of 5 average rating, 363 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

An aerial view captures the layout of Friday Harbour, featuring an expansive marina surrounded by lush greenery and residential buildings. The coastline, with a sandy beach and ample water access, provides recreational opportunities. The serene water reflects the natural beauty of the surrounding landscape.

4.85 out of 5 average rating, 186 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina, while lounging or eating outside.

Townhouse in Wasaga Beach

An oval-shaped pool is situated just steps from the sandy beach. Surrounding the pool are several lounge chairs and a shaded gazebo. The calm water of the bay is visible in the background, creating a serene setting for relaxation.

4.97 out of 5 average rating, 130 reviews

Waterfront | Heated Pool, Beachfront, BBQ, AC

Enjoy your morning coffee on your waterfront balcony in your 2 bedroom townhouse, steps away from the beautiful sands of Wasaga Beach. Fall asleep to the rhythmic sounds of the water & watch stunning sunsets from your balcony. Cotton bed linens (680 thread count) & towels included Family friendly with pool & beach- perfect for a summer getaway Located on quiet Beach 4. ~1.5 hr drive from GTA, 20 min to Collingwood/Blue Mountain. 2 parking spots. Perfect for family fun & making new memories!

The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.

4.94 out of 5 average rating, 120 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

Escape and unwind in our luxurious, open concept fully furnished 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy the season with access to golf, walking trails, beach, boating, biking, live music, events and weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Laundry

4.97 out of 5 average rating, 119 reviews

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.95 out of 5 average rating, 316 reviews

A clear view of the heated swimming pool is presented, surrounded by a well-manicured lawn. Two lounge chairs are positioned beside the pool, offering a relaxing space. Lush greenery and trees create a natural backdrop, enhancing the serene atmosphere of the outdoor area.

Cabin in Mono

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

4.99 out of 5 average rating, 185 reviews

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

4.99 out of 5 average rating, 174 reviews

The exterior of the guest home is shown, featuring a wooden facade with a slatted accent wall. A well-maintained garden with white peonies and lush green plants surrounds the entrance, which is illuminated by a subtle outdoor light. A door with a simple design is visible.

Farm stay in Essa

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

4.95 out of 5 average rating, 119 reviews

Upscale Spa Getaway w/ Private Sauna

Welcome to our most Dramatic, Romantic Spa Getaway Suite! Reconnect with your loved one in our incredible professionally designed to play with all your senses PH suite, this escape will melt away all your woes and leave you feeling refreshed and relaxed! Cozy up to any of 3 fire elements and cleanse your soul in your own private in suite infrared Sauna! Cook up a gourmet meal in our fully equipped kitchen and brand new Weber BBQ! Catch some rays in our pool and hot tub, NOW OPEN!

A spacious courtyard features a tranquil pool surrounded by modern condominium buildings. Lush greenery enhances the area, while lounge chairs are positioned near the water. Bright blue skies and natural light create a cheerful atmosphere, ideal for relaxation and leisure activities.