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.

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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

Guest house in Orangeville

4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars2 weeks 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.

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.

Top guest favourite

Home in Alton

4.97 out of 5 average rating, 92 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

KelliRating, 5 stars3 weeks ago

We loved our time at Paige's beautiful home. Such a comfortable, cozy, unique home. The stone fireplace with the wrapping stairs is so pretty. You feel you are staying somewhere special. With being out of our home for a renovation Paige provided many staples to make day to day comfortable. We definitely will recommend staying here to our friends and family.

Superhost

Home in Lisle

4.85 out of 5 average rating, 27 reviews

Hidden Oasis: Pool, Hot Tubs, & Starry Fire Pits

TeresaRating, 5 stars2 months ago

We had a fantastic experience staying at this beautiful home! From the start, the host was incredibly responsive and made sure all my questions were answered promptly. They were super friendly and welcoming. The house itself was amazing – spotless, spacious, and beautiful location. You could tell the host really cares about the space, and it had everything we needed for a comfortable and relaxing stay. We will definitely be booking here again next time we are in town. Highly recommend this place to anyone looking for a great stay!

Cottage in Mulmur

4.77 out of 5 average rating, 62 reviews

Spacious Getaway w/ Swiming Pool & hot tub

CatiRating, 5 stars1 week ago

Our stay was lovely. We were there for 3 weeks while our house was being renovated and enjoyed it very much. Only flaw was extremely slow wifi but when you’re in such a beautiful location, and with so many other activities available, we hardly noticed it. It just made it challenging when trying to conduct work calls. We thoroughly enjoyed the hot tub and pool table. Biggest disappointment was not being there later in the year to enjoy that beautiful outdoor pool! Thanks again Rahim for being so kind, responsive, and considerate to me and my family in our time of need. We are so grateful :) Truly hope we can return in the future to enjoy the properties amenities even more!

Top guest favourite

Place to stay in Laurel

5 out of 5 average rating, 21 reviews

Countryside Gem

EileenRating, 5 stars4 days ago

Amazing stay with the pool and hot tub, both of which were in great shape and comfortably clean. Hosts were very friendly and helpful. The beds are very, very firm. We would have slept much better with foam toppers on the mattresses, but that's personal preference. Surprise bonus was the basketball arcade game, which we had lots of fun with when we weren't enjoying the pool, hot tub, giant tv, games, etc. We also saw an amazing sunset out last night. Great staycation!

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Popular amenities for Dufferin County rentals with a pool

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House rentals with a pool

Guest favourite

Home in Shelburne

4.83 out of 5 average rating, 29 reviews

Primrose Park

PeterRating, 5 stars10 months ago

Rose was a wonderful host and the accommodations exceeded our expectations. Had a lovey stay and would book again.

Superhost

Home in Mono

4.38 out of 5 average rating, 8 reviews

Luxury Hockley Estate Spa

GaryRating, 5 stars4 days ago

We had an amazing stay. The place was clean, cozy, and had everything we needed for a relaxing getaway. The hot tub and pool were both incredible and made the experience even better. We’re already looking forward to coming back in the summer. I highly recommend this place to anyone looking for a fun and comfortable stay.

Guest favourite

Home in Mulmur

5 out of 5 average rating, 14 reviews

Private Pool/Pond/River in Secluded 14Acres Estate

AlyssaRating, 5 stars20 months ago

Redwood Estate was a beautiful location to host my family’s 2023 cottage weekend. The place was just as described. I’m pretty picky when it comes to accommodations, but Razia’s place was super clean and definitely met my standards! There were ten guests with us - four families - and the house was big enough for us to all spend time together and also have our own privacy. The house is well stocked - we brought a lot of stuff that we probably didn’t need to. The grounds are absolutely beautiful. Lots to see and do for all ages. The pool was of course a big hit with everyone. We just so happened to time our stay with a meteor shower and we’re able to spend the night stargazing!

Home in Mulmur

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2 bedroom apartment

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Holiday rentals with a pool in Dufferin County

Top-rated rentals with a pool in Dufferin County

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