
Holiday rentals with a pool in East Gwillimbury
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Top-rated rentals with a pool in East Gwillimbury
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for East Gwillimbury rentals with a pool
House rentals with a pool

Serene Escape: A Nature Getaway
I rented the villa for a group of 16 ladies for a golf getaway. The owners are excellent to communicate with and responded immediately to any questions or issues we had during and before our stay. The villa was spacious and well equipped with dishes ect to accommodate a large group. Beds comfortable. Unfortunately due to the weather the pool was not opened but some enjoyed the hot tub. Grounds looked like the would be very nice but again due to weather grounds we’re not manicured and grass has not been cut. Would definitely book again and hopefully next time enjoy the outdoor area. Thks for having us

2 Bd Boardwalk Condo Patio Oasis
Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan

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

Modern 5 Bedroom Home with Pool & Jacuzzi
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!

Cozy Lakefront Cottage with Hot tub and Pool.
We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

private backyard SPA oasis in Toronto
Awesome 👌 property with above average amenities and spa style options available; the hotubs alone were top notch, clean, hot and easy to use. The house itself was beautiful, well laid out and very clean. anither great property if anyone is looking to be in the mix of it all plus having the extras in your own back yard.

Luxury 2bedroom Unit in the city/heated salt pool.
We had a great time at Bessa’s. The house was beautifully decorated. The pool and back yard were amazing. We will definitely be back. I would highly recommend staying here.

King West Victorian Studio Gem
It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.
Condo rentals with a pool

Chic Studio w/ Pool | Near Lawrence West Subway
Andrews Place is perfect for a solo traveler. The property is clean, private, and offers excellent transport access to very interesting places. You can catch a direct bus from Toronto YYZ Airport with no need to change buses, and it's just less than a 10-minute walk to the property from the bus stop. It was truly great value for money.

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Loved our stay here!! Can't say enough positive things about our vacation here. Kitchen was fully stocked, clean bathroom and rooms, easy check in and check out and excellent cooling system as it was a hot few days. Amenities were great and welcoming for families, environment was peaceful and we also loved how the balcony backed onto trees and nature. Would 100% stay here again in the future. Thank you!

Friday Harbour Ground Floor w/ Large Terrance
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

Downtown Markham Unionville
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!

Cozy south view suite overlooking the nature trail
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!

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

Friday Harbour Luxury Condo Escape, Sleeps 4
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

Lake Simco penthouse at Friday Harbour resort
Such a beautiful place!! Anastasia was super responsive. Would definitely visit again
Quick stats about holiday rentals with a pool in East Gwillimbury
Total rentals
10 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
120 reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Costco Wholesale, Metro and SilverCity Newmarket Cinemas
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Osler Bluff Ski Club
- Horseshoe Resort
- Toronto City Hall