Vacation rentals with a pool in Greater Toronto and Hamilton Area

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...

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.

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

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

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

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

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.

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!

Niagara Luxury villa-hottub, pool, water view

Note: Pool & hottub are open. Welcome to my Niagara Villa.(License B&B facility). This luxury villa offers spectacular décor,private backyard oasis, complimentary breakfast. Guest unit has private entrance,2 Bedrooms,2 washrooms(1 with sky light),full kitchen with cooking facility,dinning & living area has 2 TVs, sofa bed. Only guests are using private backyard with hottub (running whole year), kids play, 50,000 lit big pool and 2 big Gazabos. Note:Host is living in the separate unit.

“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”

Chalet w/ yard & pool, walk to beach & playground

Barrie's most comfortable and friendly chalet, with a rustic ambience that has had a documentary filmed in it! Warm and luxurious with A/C, gas fireplace and gourmet kitchen, with park. beach and playground on Lake Simcoe a two minute walk away. A welcoming, fully equipped home away from home for families, couples, friends and travellers in a beautiful, mature neighbourhood featuring nearby walking and biking trails. For longer stays we are happy to offer discounts, just inquire!

Lake & Vine Collection | Poolside Retreat

Welcome to Poolside Retreat, Lake & Vine Collection’s premier summer escape. This private vacation home features a large in-ground swimming pool, expansive backyard, inviting outdoor living spaces, and thoughtfully designed interiors for families and groups. Whether you’re swimming, dining outdoors, or simply relaxing by the pool, this home offers the perfect setting for an unforgettable Niagara-on-the-Lake getaway. It's really an ideal destination for creating lasting memories.