Holiday 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.

4 of 12 items showing

1 of 3 pages

Top Guest favourite

Home in Mono

4.97 out of 5 average rating, 38 reviews

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars5 months ago

We had an amazing stay! Communication with the hosts was quick, and they were very attentive to all our needs, ensuring we had everything we required. The house was perfectly suited for our group of 8, offering plenty of space and comfort. The property itself is beautiful, with easy access to scenic walks and hikes right on the grounds. Plus, it was just a short drive to Hockley Valley, where we attended our event. This place was ideal for our weekend getaway, and we’d definitely stay here again!

Guest favourite

Guesthouse in Orangeville

4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars2 days ago

What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.

Top Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 744 reviews

HotTub & Fireplace Getaway - Headwaters Retreat

NathanRating, 5 starstoday

We enjoyed our stay at Susan's place! Quiet, private and had a real homey feel... and the hot tub was a nice touch! would certainly rent again!

Superhost

Home in Orangeville

4.67 out of 5 average rating, 9 reviews

Private cottage heated pool/HotTub/Games 20 Acre

AmarRating, 5 stars2 weeks ago

We stayed here for my daughter’s birthday. Great property for a big group. Beautiful surroundings and great peaceful setting. Big common areas/spaces for kids to move around in the house. The basement had TT and pool table which were great for entertainment. Brendan is a great host who is friendly and responds on time and helpful if you face any issues. Would love to visit again.

Guest favourite

Home in Mono

4.89 out of 5 average rating, 37 reviews

Mono Springs - Dream Country Escape w pool/hot tub

VikramRating, 5 stars2 months ago

“A Slice of Heaven on Earth” We had the most incredible stay at this breathtaking property! Nestled on 10 sprawling acres, this magnificent estate exceeded our wildest dreams. The moment we stepped foot on the grounds, we knew we were in for a treat. The property itself is stunning, with beautifully manicured lawns, serene walking trails, and picturesque views that seem to stretch on forever. We spent hours exploring the grounds, discovering hidden gems and soaking up the tranquility. The location is equally impressive, offering the perfect blend of seclusion and accessibility. We felt like we were a world away from the hustle and bustle, yet still within easy reach of local amenities. Our hosts were warm, welcoming, and incredibly attentive, ensuring our stay was nothing short of perfection. If you're looking for a truly unforgettable experience, look no further! This incredible property has left us with memories we'll cherish forever.

Cottage in Mulmur

4.77 out of 5 average rating, 61 reviews

Spacious Getaway w/ Swiming Pool & hot tub

AsishRating, 5 stars2 weeks ago

We had a beautiful stay! The place felt more like home which was nice and warm. It had all the amenities that we required for our stay.. Our family enjoyed the stay especially the hot tub, billiards game, table tennis, and foos ball game and our trail walks.. Rahim was extremely helpful and answered all our queries promptly and made sure that our stay was comfortable. We as a family would highly recommend this place to everyone who would want a nice cozy home for a weekend getaway! Thank you Rahim for hosting us and helping us out! The house is lovely and we intend to visit again in summers..

Top Guest favourite

Place to stay in Laurel

5 out of 5 average rating, 18 reviews

Countryside Gem

JenniferRating, 5 stars1 week ago

We really enjoyed our time at Kevin’s place. My mom was able to manoeuvre her way around with her walker quite easily, so it was quite spacious. Everything was spotless and the kitchen was well-stocked without being cluttered. We asked several questions and always received a quick response.