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 Vaughan
5 out of 5 average rating, 5 reviews

Vacation Getaway with Heated Spa-Pool Open365 Days

YasminRating, 5 stars1 month ago
I had an amazing experience staying at this beautiful home. The property was exactly as described, and even better in person! It was clean, spacious, and thoughtfully decorated, making it feel like a home away from home. The host was incredibly welcoming and responsive, ensuring that we had everything we needed for a comfortable stay. The location was perfect, with easy access to local attractions and amenities. I highly recommend this place to anyone looking for a relaxing and enjoyable stay. Can't wait to return!
Superhost
Home in Newmarket
4.73 out of 5 average rating, 26 reviews

"THE BIRD HOUSE" getaway!

MargotRating, 5 stars7 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.
Top Guest favourite
Home in Toronto
4.98 out of 5 average rating, 43 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

CarmalettaRating, 5 stars1 month ago
This house was beautiful! Comfortable and relaxing the master shower was to die for! On top of that jasmine and Keith really was proactive and attentive to us and whatever we needed they were able to supply us with and was really kind sweet and amazing couple to work with over all! Definitely will book here again
Superhost
Home in Newmarket
4.82 out of 5 average rating, 22 reviews

Cozy Pool house in Newmarket

FabrizioRating, 5 stars8 months ago
Great stay. Brought the family there for a weekend of pool fun. My kids are 3 and 16 months. Minoo is a great host and very responsive. The home is meticulous but not particularly kid friendly - she was upfront and described this to me in advance. If you have a little one that likes to explore on their own - you need to keep an eye on them, lots of little decorations at arms reach for the kids. Spiral staircase can be difficult to use with kids in your arms as well. Pool was beautiful and warm however is not a walk in and the shallow end is a third of the pool. We spent most of our time in the private backyard or out for walks. Local parks and amenities close by. We had a great time and would absolutely stay at Minoos place again when visiting Newmarket. Thanks for the hospitality Minoo !!
Superhost
Home in Toronto
5 out of 5 average rating, 3 reviews

Modern Home with Pool & Jacuzzi [no cleaning fee]

Yalealem Rating, 5 stars5 months ago
We had a wonderful stay at Angie's house. The place is amazing—clean, bright, and welcoming. The host is incredibly sociable, friendly, positive, helpful, and proactive. Overall, we had a fantastic time, and I just want to say thank you!
Superhost
Home in Georgina
4.72 out of 5 average rating, 29 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

NarthakiRating, 5 stars2 days ago
Had a great weekend with my family! Host was extremely fast are responses which helped out a lot. Suggestion bring your own pillows as pillows for us were a little too flat, but other than that gorgeous place. Grocery stores and food spots were very close to us and we had a great time!
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 months ago
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.
Guest favourite
Home in Toronto
5 out of 5 average rating, 13 reviews

Luxe, Family-Friendly Oasis Home With Pool

SergeRating, 5 stars4 months ago
Great place with all the amenities for a family of 5. Easy access from airport. Great host that was responsive throughout our stay. Would highly recommend.

Condo rentals with a pool

Superhost
Condo in Innisfil
4.82 out of 5 average rating, 471 reviews

Lovely 2-bedroom at Friday Harbour

AllisonRating, 5 stars1 week ago
The location is perfectly located within Friday Harbour to access the restaurants and stores. Lots to do. Felt very safe inside the condo, very clean, kitchen was fully stocked with everything we needed to cook and eat. Beds are comfy!
Guest favourite
Condo in Innisfil
5 out of 5 average rating, 62 reviews

FH Aquarius Bldg: Modern 2BR/2B Condo

CristinaRating, 5 stars1 month ago
Beautiful unit with fully equipped kitchen & everything you need to feel right at home. Beds are comfortable, we were 2 people but it would fit 4 comfortably. Would definitely be back.
Top Guest favourite
Condo in Innisfil
4.98 out of 5 average rating, 60 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

GloriaRating, 5 stars2 weeks ago
Very nice and peaceful location, had an amazing and relaxing time with my family. Host was very responsive and accommodating, great value for money. It felt like home, with amazing restaurants, overall great experience… Hope to be back in summer!
Guest favourite
Condo in Markham
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars2 months ago
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!
Guest favourite
Condo in Innisfil
5 out of 5 average rating, 12 reviews

Luxurious Friday Harbour Condo

Alex & JessicaRating, 5 stars2 days ago
Enjoyed our stay. Great spot for a family.
Superhost
Condo in Innisfil
4.9 out of 5 average rating, 201 reviews

Beautifully Furnished New Condo at Friday Harbour

NicoleRating, 5 stars2 months ago
We had a great stay! The place was incredibly clean, and had everything we needed and more. We felt right at home, and communication with the host was excellent! Everything was easy to find. There was an awful snow storm over the weekend that we stayed, but the place was so cozy and clean, we were happy to stay in and binge watch some Netflix :) I can’t recommend Jennifer Nicole’s place enough!
Guest favourite
Condo in Innisfil
4.98 out of 5 average rating, 45 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Hernán DaríoRating, 5 stars2 weeks ago
Jack truly turned his apartment into an oasis away. The interior decor was absolutely stunning and made us feel like we were in our own bubble away from the real world. Being in the Friday Harbour neighbourhood was a perfect location to have a leisurely weekend with stunning views, great restaurants and a relaxing vibe all around. Would definitely recommend this place again!
Guest favourite
Condo in Innisfil
4.87 out of 5 average rating, 23 reviews

2 Bed/2 Bath Condo w/ Pool & Hot Tub | Lake Simcoe

ChristineRating, 5 stars1 week ago
Outstanding SUPERHOST!!! Matteo & Laura were the easiest people to communicate with… having stayed in several Airbnb‘s both internationally and domestically barnone these two bring a new meaning to the word super host halfway through my stay I received an extravagant basket filled with wonderful thoughtful gifts along with extra supplies, they thought I would be needing! They even went as far as including a gift card to their upscale restaurant! I felt more like a spoiled child than a guest in their condo! Keep up the extraordinary hospitality!! It goes a long way in this industry! I have only just checked out, and will be returning in a week for another extended stay.

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