Holiday rentals with a pool in Regional Municipality of York

Find and book unique homes with a pool on Airbnb

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Popular amenities for Regional Municipality of York rentals with a pool

House rentals with a pool

Guest favourite
Home in East Gwillimbury
4.96 out of 5 average rating, 23 reviews

Private river access with pool, canoes, kayak

SrinidhiRating, 5 stars1 month ago
Clean space, amenities were good! Responsive host!
Guest favourite
Home in Innisfil
4.92 out of 5 average rating, 48 reviews

2 Bd Boardwalk Condo Patio Oasis

DavidRating, 5 stars2 weeks ago
Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan
Guest favourite
Home in Barrie
4.93 out of 5 average rating, 94 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

DianeRating, 5 stars1 week ago
This house was perfect for our large group: for couples and a baby. Having the pool was a bonus that we really appreciated in the warm weather. The kitchen was extremely well equipped, and there were enough linens as well as pool towels for us all. There was plenty of space for everybody as the rooms were all quite large, particularly the master bedroom. The house were incredibly accommodating when we realized after checkout that we had left a couple of items behind. They were able to make arrangements for us to retrieve them several days later back in Toronto! I definitely can recommend this house.
Guest favourite
Home in Toronto
5 out of 5 average rating, 13 reviews

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars3 weeks ago
My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!
Top Guest favourite
Home in Toronto
4.98 out of 5 average rating, 49 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars1 week ago
We had a delightful stay at Jasmine’s place. The space was impeccably clean and thoughtfully decorated, making it feel like a true home away from home. Jasmine was an exceptional host—attentive, communicative, and always ready with helpful replies with my questions. I highly recommend her place to anyone visiting the area and would love to return in the future.
Superhost
Home in Newmarket
4.73 out of 5 average rating, 26 reviews

"THE BIRD HOUSE" getaway!

MargotRating, 5 stars8 months ago
Megan’s house was just like the pictures. It had lots of beds which was perfect for family traveling to town for a family wedding. The pool table and heated pool were an added bonus.
Superhost
Home in Georgina
4.75 out of 5 average rating, 32 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

MeenuRating, 5 stars1 month ago
Myself and my friends had a pleasant staycation at Xin’s house in May. I had given a heads up that there will be a 4 months baby with us and they made sure the entire space is clean making it most comfortable especially for the baby. The host was super responsive from the time I booked and replied to my questions in a timely and respectful manner. Highly recommend to anyone looking for a spot not very far from city yet appreciate a peaceful and relaxing atmosphere.
Superhost
Home in Cedar Valley
5 out of 5 average rating, 5 reviews

Forest House | Golf/Hiking/Horse Riding Nearby

BrandonRating, 5 stars3 weeks ago
Had a really good time here place was beautiful. Would defiantly recommend if your looking for a weekend get away!! Hosts went above and beyond to make sure our stay was amazing.

Condo rentals with a pool

Guest favourite
Condo in North York,
4.96 out of 5 average rating, 55 reviews

1 Bedroom Suite

SimonRating, 5 stars1 month ago
The space was wonderful and so was our host. Couldn’t have been happier. Thanks so much for letting us stay and being so accommodating Azeta!
Guest favourite
Condo in Innisfil
4.94 out of 5 average rating, 35 reviews

Cozy south view suite overlooking the nature trail

KimberlyRating, 5 stars3 weeks ago
Loved our stay! Place was spotless and just as described, and check-in was smooth with clear instructions. Unfortunately the Nature Preserve was closed during our stay, and the pool was closed for maintenance, but Lina was accommodating otherwise. One thing to note is that the unit is right next to a stairwell exit, so if you have a sensitive dog like ours, they may be disturbed by some noises. Thanks again for the great stay!
Guest favourite
Condo in Richmond Hill
4.95 out of 5 average rating, 21 reviews

Chic Richmond hill Condo

BillyRating, 5 stars5 days ago
Andrea responded very quickly to any questions we had. Good location, handy transport by bus and subway to the centre of Toronto in under an hour. We would certainly use again if we come back to Toronto.
Superhost
Condo in Innisfil
5 out of 5 average rating, 26 reviews

Elegant 2bdrm/2bath condo at Friday Harbour

AngelRating, 5 stars10 months ago
Mary was very accommodating! The place was clean. The appliances were in great condition. She provided everything that we needed during our WHOLE stay. Most places we’ve been at jist gives us a starter kit, but Mary went above and beyond to make our stay enjoyable, and well taken care of. She even gave our kiddos bubble wands when we came in. It’s the little touch that gives the biggest meaning. Thank you! The only thing we wish there was, was more storage. We kept our clothes in our luggages. The rack could use some storage bins maybe? So that we can store clothes in it without it calling off the shelves. But overall the stay was just great! If we come back to Friday harbour again, we sure will come back to Mary!
Superhost
Condo in Innisfil
4.91 out of 5 average rating, 142 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

AnisaRating, 5 stars1 month ago
My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!
Guest favourite
Condo in Innisfil
4.89 out of 5 average rating, 19 reviews

Enjoy your stay at a cozy One bedroom apartment!

YugrajRating, 5 stars3 months ago
"Peaceful and Convenient Stay!" I had a great stay at this Airbnb! The place was very peaceful, making it perfect for relaxation. The location is incredibly convenient—just a 2-minute walk to Starbucks, FH Finefood grocery store, and plenty of restaurants. It made everything super easy, whether I needed coffee, groceries, or a nice meal. The host was also responsive and helpful. I’d definitely recommend this place and would love to stay again.
Guest favourite
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

SoniaRating, 5 stars9 months ago
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive
Top Guest favourite
Condo in Innisfil
5 out of 5 average rating, 36 reviews

Charming 2BD/2BTH with Hot Tub at Friday Harbour

IlonaRating, 5 stars3 weeks ago
Amazing place! Very clean and lots of helpful information! Will definitely come back.

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