Vacation rentals with a pool in Caledon

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...

Location · Value · Cleanliness

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.

Value · Family · Wifi

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Family · Location · Layout

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

Value · Location · Laundry

Utopia villa and spa

Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

Location · Family · Access

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!

Location · Family · View

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

Family · Value · Beach

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Value · Family · Sleep quality

Separate apartment with pool, on golf course.

Enjoy a newly renovated studio apartment with a private entrance and exclusive access to a serene inground pool. This cozy space is furnished with Restoration Hardware pieces and features a fully equipped kitchen, high-speed WiFi, and a patio with an outdoor barbecue—perfect for remote workers or a peaceful getaway. Situated behind Caledon Woods Golf Course, it’s just 7 minutes from the Caledon Equestrian Park, 30 minutes from Pearson Airport, and close to highways leading to Toronto.

Value · Location · Biking

Private HotTub & Pool - Headwaters Retreat

Escape to our modern and rustic Queen Suite, with private hot tub right at your door. Relax by the pool, or unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or a quiet escape away. Book now for your ultimate getaway in comfort and nature!

Value · Family · Comfort

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

Family · Location · Amenities

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

Value · Location · Getting around