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

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 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.

Jan 27 – Feb 3

€ 187 per night

Guest favorite

Home in Mono

4.97 out of 5 average rating, 29 reviews

Country Family Getaway with private 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.

May 31 – Jun 7

€ 543 per night

Guest favorite

Home in Erin

4.8 out of 5 average rating, 10 reviews

Estate House~Hot Tub~Sauna~Heated Pool~OasisD'Erin

Welcome to our incredible country retreat in Erin. This property has it all for you and your family to relax and enjoy the countryside. Features: ✓ Outdoor barrel sauna and hot tub (year-round) ✓ 4 Spacious and well-appointed bedrooms with 5 beds ✓ Huge driveway with parking for up to 8-10 vehicles ✓ Less than 10 minutes to ski hills, nature trails, golf, Millcroft spa ✓ High-speed internet ✓ Comfortable bedrooms with high-quality linens ✓ A large heated swimming pool (seasonal: May-October)

Jun 8 – 15

€ 812 per night

Guest favorite

Home in Mono

4.88 out of 5 average rating, 24 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

May 24 – 31

€ 730 per night

Guest favorite

Home in Alton

4.96 out of 5 average rating, 70 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

This beautiful 3 bedroom , 1.5 bathroom house in the quaint village of Alton can sleep 6-8 people. It is the perfect size for a medium sized family. The house in located right in the village, backing on to a shallow flowing part of the credit river. You are able to enjoy the sounds of nature and views right from the Muskoka chairs placed along the river bank. The outdoor above ground pool is available for use during summer months. Less then a 2 min walk to the Millcroft Inn & Spa.

Dec 15 – 22

€ 238 per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private HotTub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

€ 84 per night

Guest favorite

Chalet in Mulmur

5.0 out of 5 average rating, 29 reviews

Into the Woods Log Home

Super private and relaxing escape, only 1:20 hrs from Toronto, and 40 minutes to Collingwood. Amenities include: - swim spa pool (seasonal) and hot tub - 2 swimming ponds - 70 acres of land (with trails) - sauna and steam shower - pirate ship play structure - ice rink (seasonal) - fireplaces - kids' zip line ... You'll never want to go home! This is our family log home. Pls make sure you can abide by our house rules before booking. See more on IG @intothewoodsloghome

Nov 6 – 13

€ 848 per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Feb 9 – 16

€ 179 per night

Superhost

Home in Orangeville

4.72 out of 5 average rating, 43 reviews

20 Acre of privacy with Heated Pool and Hot Tubs

20 Acres of pure privacy. We welcome you to our little private getaway from the busy city. Enjoy the hot days in our heated Pool and gathering in our backyard patio. Our Hot tubs is ready for you to use on the colder days/nights. Kids can definitely bring their tents to enjoy the outdoor. - 14 min from popular Mono Cliffs Provincial Park - 7 minutes from popular Hockley Valley Resort for skiing (winter), spa and golf in the summer - 45 min from Airport

Jan 17 – 24

€ 804 per night

Guest favorite

Cottage in Mulmur

4.89 out of 5 average rating, 27 reviews

Spacious Getaway w/ Swiming Pool-Great for Groups!

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

Sep 16 – 23

€ 530 per night

Bungalow in Township Of Mulmur

5.0 out of 5 average rating, 7 reviews

Ideal location for activities in all seasons

YOUR four season oasis awaits you. 85 acres of total privacy, nestled in the Mulmur Hills near Shelburne On with a 8- acre private pond . Fishpond is tailor-made for family gatherings. Hiking, fishing, swimming or a paddle on the pond in summer. In winter downhill and cross- country skiing, snow-shoeing Private swimming pool and tennis court are included Just over one hour's drive north-west from Toronto's Pearson Airport.

Mar 15 – 22

€ 384 per night

Guest favorite

Bungalow in Orangeville

5.0 out of 5 average rating, 37 reviews

Stunning Family Retreat, 1hr from TO, Sleeps 15

Nestled in Mono, this serene 5-star retreat estate is a guest favourite, just under an hour from Toronto, and accommodates 15. It is only 10 minutes from Hockley Valley Ski Resort and features private access to Island Lake for snowshoeing and skating. Enjoy Beautiful Summer days by the pool in a setting where luxury blends with comfort, creating the perfect backdrop for relaxation and feeling right at home.

Jan 30 – Feb 6

€ 599 per night