Holiday rentals with a pool in East Gwillimbury

Find and book unique homes with a pool on Airbnb

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Popular amenities for East Gwillimbury rentals with a pool

House rentals with a pool

Guest favourite
Home in Utopia
4.87 out of 5 average rating, 47 reviews

Serene Escape: A Nature Getaway

DonnaRating, 5 stars4 weeks ago
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
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.
Superhost
Home in North York
5 out of 5 average rating, 3 reviews

Modern 5 Bedroom Home with Pool & Jacuzzi

Yalealem Rating, 5 stars7 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!
Guest favourite
Home in Elmvale
4.89 out of 5 average rating, 19 reviews

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago
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 🌎.
Superhost
Home in Mimico-Queensway
4.87 out of 5 average rating, 46 reviews

private backyard SPA oasis in Toronto

WadeRating, 5 stars2 weeks ago
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.
Superhost
Home in Central Etobicoke
4.89 out of 5 average rating, 9 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

TanyaRating, 5 stars9 months ago
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.
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 304 reviews

King West Victorian Studio Gem

TamerRating, 5 stars5 days ago
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

Superhost
Condo in North York
4.8 out of 5 average rating, 104 reviews

Chic Studio w/ Pool | Near Lawrence West Subway

KayodeRating, 5 stars3 days ago
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.
Guest favourite
Condo in Oro
4.79 out of 5 average rating, 106 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

DestinyRating, 5 stars3 days ago
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!
Top Guest favourite
Condo in Innisfil
5 out of 5 average rating, 33 reviews

Friday Harbour Ground Floor w/ Large Terrance

AshleyRating, 5 stars1 week ago
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!
Guest favourite
Condo in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars3 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
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!
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
4.94 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
Guest favourite
Condo in Innisfil
4.88 out of 5 average rating, 215 reviews

Lake Simco penthouse at Friday Harbour resort

MopinaRating, 5 stars4 days ago
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

Destinations to explore

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  2. Canada
  3. Ontario
  4. East Gwillimbury
  5. Rentals with pools