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

Home in Mono

4.97 out of 5 average rating, 38 reviews

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars1 month 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 favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 348 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

KaylaRating, 5 stars1 month ago

We enjoyed a nice mini vacation at Sunny Pines. We spent some time at the Scandinave spa and did some shopping in Collingwood which was about a 45 minute drive away. The property is beautiful and access to the sauna was a nice bonus. Everything we needed was there and the loft was very clean with fresh towels and linens. The only criticism would be that the instructions to the building weren’t clear (it’s the loft on top of the garage). We would definitely recommend this Airbnb to those looking for a relaxing weekend away.

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 717 reviews

Headwaters Retreat - HotTub & Cozy Fireplace

JenniRating, 5 stars2 days ago

Terrific stay. I can see why Susan was a an ambassador for Airbnb as everything was well thought out and provided for. Clean, comfortable and the hot tub was a bonus. I imagine in the summer access and looking out over the reserve behind the house would be lovely. Very much recommend.

Cottage in Mulmur

4.73 out of 5 average rating, 49 reviews

Spacious Getaway w/ Swiming Pool & hot tub

SaloomehRating, 5 stars3 weeks ago

Fantastic experience at this cottage! We had an absolutely fantastic time staying at Rahim’s place. From start to finish, everything exceeded our expectations. The communication with Rahim was smooth and prompt, making the booking and checking process hassle-free. We enjoyed exploring the area, and relaxing in the SPA, we gained so much energy and had a memorable time. Can’t wait to come back as soon as possible! Thanks Rahim!

Guest favorite

Cabin in Mono

4.95 out of 5 average rating, 293 reviews

The Trails Retreat (Private Cabin)

KaelanRating, 5 stars3 weeks ago

This cabin is a nice, relaxing little getaway not too far from the city. Very cozy. The hosts are very polite and respectful and the cabin was extremely clean. By far, one of the cleanest Airbnb's I've ever been to. The trails on the property are a nice touch, as is the wood burning stove. Anything you could need is within a 15 minute drive from the location. It's the perfect balance of having a little nature and peace while still having access to everything a city provides close by.

Bungalow in Township Of Mulmur

4.86 out of 5 average rating, 14 reviews

Ideal location for activities in all seasons

IanRating, 5 stars3 months ago

Victor’s place was by far the best Air BnB I’ve ever stayed at. Very well thought out and has everything. Private and tranquil. Would highly recommend to anyone. This place is truly a hidden gem. The price is a very great deal considering what you get. Massive property with nobody around. Beautiful lake size pond with a pool! Everything’s spotless and clean. Couldn’t ask for more. Will definitely keep this place in mind for cottage getaways in the future.

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Popular amenities for Dufferin County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favorite

Home in Shelburne

4.83 out of 5 average rating, 29 reviews

Primrose Park

PeterRating, 5 stars6 months ago

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

Guest favorite

Home in Mulmur

5 out of 5 average rating, 14 reviews

Private Pool/Pond/River in Secluded 14Acres Estate

AlyssaRating, 5 stars16 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!