Vacation rentals with a pool in Dufferin County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dufferin County

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

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Guest favorite

A spacious heated pool is surrounded by lush greenery and colorful flowers. Lounge chairs provide seating options, while a vibrant umbrella offers shade. The pool area includes a patio, decorative plants, and a fenced perimeter, creating a serene outdoor retreat.

Home in Mono

4.96 out of 5 average rating, 49 reviews

Country Family Getaway with Pool and Trails

This charming restored stone farm house with stained glass windows that look out over the well landscaped property with stone walls, heated pool & mature fruit and maple trees. Perfect for a family vacation on nearly 100 acres of private flora, fauna and pristine streams or simply enjoy local cultural offerings . Also an ideal location for special events. A 9-hole golf course and The Bruce Trail, Split Rock Narrows, Dufferin County Forest are among other famed nature reserves just minutes away.

Top guest favorite

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.

Guesthouse in Orangeville

4.95 out of 5 average rating, 373 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.

Top guest favorite

A well-maintained outdoor pool area is surrounded by lush greenery and tall trees. The pool features a wooden deck with a sun lounger positioned nearby. Bright red flowers add a touch of color to the scene, enhancing the inviting atmosphere.

Guest suite in Orangeville

4.92 out of 5 average rating, 783 reviews

Cozy Hot Tub Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, 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 just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Superhost

A spacious cottage is surrounded by greenery, featuring a circular outdoor pool and patio area. A hammock is positioned in the foreground, inviting relaxation. Nearby, outdoor seating and umbrellas are visible, providing a comfortable space for gatherings amidst the peaceful countryside.

Home in Orangeville

4.81 out of 5 average rating, 26 reviews

Private cottage heated pool/HotTub/Games 20 Acre

Nestled in a serene countryside setting, this charming cottage offers a perfect blend of rustic charm and modern comfort. Step outside to discover a private outdoor heated pool and hot tub, each offering a soothing retreat. Whether you’re enjoying a peaceful morning swim or hosting friends for a sunset soak, this cottage with its outdoor heated pool and hot tubs is an idyllic escape for any getaway. Nearby Attractions: - TPC Toronto Opsrey Golf - Hockley Resort Ski/Spa - Provincial Park

Guest favorite

A spacious backyard features an in-ground pool surrounded by a concrete deck. Red lounge chairs are positioned nearby, offering a relaxing spot. The two-story house is visible in the background, complemented by lush greenery and trees that provide a natural setting.

Home in Mono

4.91 out of 5 average rating, 46 reviews

Mono Springs - Dream Country Escape w pool/hot tub

Welcome to Mono Springs! Our straight-out-of-a-storybook family retreat, located in the heart of Mono. Lovingly renovated with all new furnishings, this dream country escape with rustic finishes sits on 10 acres of gorgeous landscape and fields with pre-made trails ready to explore giving wholesome Cottage-Vibes. Plenty of space for everyone with lots of quiet sitting areas, both inside and outside, private hot tub and heated pool. Ideal setting for family get togethers and nature enthusiasts

Top guest favorite

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

4.95 out of 5 average rating, 322 reviews

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!

Top guest favorite

Home in Alton

4.97 out of 5 average rating, 104 reviews

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • 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

The spacious home is set against a backdrop of trees, featuring a modern exterior and a large patio area. An in-ground swimming pool is framed by neatly arranged flower beds, while the sunset casts a warm glow over the scene.

Cottage in Mulmur

4.66 out of 5 average rating, 90 reviews

Spacious Getaway w/ Swiming Pool OR hot tub

Escape to your own private paradise with this stunning 4 BED, 3 BA (5 queen beds and 4 folding beds) on 8 acres of lush greenery. Perfect for large families or groups of friends seeking fun and tranquility. Relax in our brand-new hot tub, take a dip in the in-ground pool, or explore the private walking trail. Enjoy five cozy queen beds, an open-concept living and dining room, a foosball table, a spacious pool table room, and ping-pong. Book now for an unforgettable experience!

An outdoor area features a swimming pool surrounded by grass, with lounge chairs arranged nearby. A small shed with garden vines stands adjacent to the pool, adding texture to the landscape. In the background, a two-story building provides additional space for relaxation.

Guest suite in Mono

5 out of 5 average rating, 4 reviews

Hilltop on Cedar Lane

Discover our special retreat, just 12 minutes from the picturesque Hockley Valley Resort, where you can enjoy skiing, golfing, and a luxurious spa. Only 13 minutes from the Mansfield Ski Club, our location offers easy access to thrilling winter and summer sports. Nestled near the Mono Mills Trails, it’s the perfect spot for outdoor enthusiasts. Enjoy a relaxing and convenient escape from the city, blending comfort with adventure. *****Pool is open until mid October! *****

Superhost

Home in Mono

4.63 out of 5 average rating, 27 reviews

Luxury Hockley Estate Spa

Kick back and relax in this calm, stylish space. This home is located in a central location close to Orangeville and hockley Valley ski/ winery/hiking. The home is just like a relaxing spa with pool, hot tub, sauna, indoor wood burning stove, outdoor BBQ, massive kitchen, lots of space. Great for family dinners and getaways, we enjoy groups with longer stays and will give monthly discounts.. This amazing property has it all:)

Top guest favorite

A modern tiny home is nestled among trees, featuring large glass doors that open to a patio area. Two small chairs are positioned on the deck beside potted plants, while gravel paths lead through the campground, enhancing the tranquil outdoor setting.

Shipping container in Mono

5 out of 5 average rating, 10 reviews

The White House

Discover the gorgeous landscape that surrounds this place to stay. It is located in our campground. We just opened it up to you, this is a brand new space. Ideal for 2 people or add in one child that can sleep on the couch. You can have a campfire, time alone, come rain or shine. You can join in on the activities or just do your own thing. Share our public pool, walking trails, volleyball net, pond site.

Superhost

Home in Lisle

4.42 out of 5 average rating, 43 reviews

Spacious 4BR Country Retreat with Fire Pit & BBQ

Nestled in south-central Ontario, our 3000 sq ft home sits on a sprawling 100 acres, blending vintage charm with modern comfort. With 4 cozy bedrooms, 2 living spaces, and a backyard perfect for evenings around the BBQ and fire pit, it's ideal for families. Plus, we're just minutes from ski resorts, golf clubs, and museums. Come make memories with us! Note: Pool is NOT available