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Family-friendly holiday rentals in East Gwillimbury

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Popular amenities for East Gwillimbury family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Midtown
4.96 out of 5 average rating, 46 reviews

Great Davenport Hillcrest House

DylanRating, 5 stars4 months ago
Our trip was made better by staying her. The house is beautiful and comfortable and Ottilie wad a courteous and wonderful host. well worth the cost
Guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 312 reviews

Beautiful Condo + CN Tower View + Free Parking

LazloRating, 5 stars2 weeks ago
Great clean place, exactly as advertised, well situated. Katherine was kind enough to accomodate us with a very early check-in while we were stuck and stranded in the snowstorm.
Guest favourite
Condo in Unionville
4.91 out of 5 average rating, 113 reviews

Downtown Markham Unionville

AndreaRating, 5 stars2 days 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 Downtown Toronto
4.89 out of 5 average rating, 832 reviews

1 Bedroom Suite - Downtown Core (near MTCC/Rogers)

EricRating, 5 stars2 months ago
Calvin was very responsive whenever I had questions and even let me know that we were able to check-in earlier than expected. The room was spotless and had every amenity we needed for cooking and entertainment. Within walking distance of many holiday events and countless food and bar options available; I can’t speak enough for how great the location is. Would definitely come again
Superhost
Condo in Downtown Toronto
4.87 out of 5 average rating, 326 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

JuliaRating, 5 starstoday
Lovely place , felt right at home . Crystal was very helpful and responsive, given it was a very last minute booking. The street was very quiet and so was the building itself . Very cozy getaway in the heart of downtown Toronto for an incredibly good price . Thank you so much for making our short stay nothing short of AMAZING !
Superhost
Condo in Downtown Toronto
4.86 out of 5 average rating, 100 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

EricRating, 5 stars3 months ago
The place was excellent and suited our needs quite well. We were there for a show at the Rogers Centre, which was close to us, around a 10-minute walk.
Guest favourite
Home in Sebright
5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

AaronRating, 5 stars6 months ago
Gary & Mina were excellent hosts. They greeted us for check in and where very accommodating. Any questions we had were quickly answered via the AirBNB app. The house was full of character and had lots of things to do indoors and outdoors. The kitchen was well stocked with supplies, utensils and kitchen wares. There was a washer/dryer centrally located which was great for towels and the Weber BBQ was in top notch condition. Water toys well maintained (2 kayaks, 1 paddle board, 1 canoe and 1 paddle boat). Pool and hot tub worked great, which was a must for our cottage getaway.
Superhost
Cottage in Orillia
4.73 out of 5 average rating, 207 reviews

Waterside Haven: spacious retreat w/hot tub

JenniferRating, 5 stars2 months ago
We had a wonderful time at this beautiful house. There were plenty of amenities and lots to do nearby. It was spacious and the hot tub was the perfect touch. We were very happy with everything ❤️

Family- and pet-friendly home rentals

Guest favourite
Home in Roncesvalles Village
4.92 out of 5 average rating, 144 reviews

Cozy one bedroom apartment in Roncesvales village

LukeRating, 5 stars2 weeks ago
We had a wonderful stay at Seher’s place over Valentine’s weekend with my wife and our dog. We stayed for three nights, and from start to finish, Seher was an exceptional host. She was proactive in communication, always quick to respond, and went out of her way to assist us with anything we needed. Her kindness and hospitality truly stood out. The space itself is impeccably clean, well-organized, and thoughtfully stocked with all the essentials—and more! It had everything needed for daily living, plus thoughtful extras like snacks, coffee, and tea, which we really appreciated. Parking is on the street, but it’s easy to arrange through the City of Toronto. Seher even guided us through the process and was kind enough to print out the permit for us, making everything hassle-free. Overall, I highly recommend this place for both short and long stays. With such a welcoming and attentive host, it’s an excellent choice for anyone visiting Toronto!
Guest favourite
Condo in Downtown Toronto
4.93 out of 5 average rating, 155 reviews

Beautiful suite in Downtown Toronto

JessRating, 5 stars3 months ago
My 7 year old daughter and I flew in to Toronto for Taylor Swift's ERAS concert. I can not say enough about the location. The Rogers Center is right across the street- we could watch the line up at our gate and then head over when there was no line. Amazing view of Rogers Center and CN tour. We walked everywhere the entire time- CN Tower, Ripley Aquarium, Convention Center for the Tayl-gate party and could easily rest at the condo in between activities. The condo was super clean. The bed was SO COMFY! Fully stocked kitchen. My mom came to visit us for a night from Windsor and Oron was extremely responsive to my request for parking. He got us set up right away. I would 100% stay here again for an event!
Guest favourite
Condo in Downtown Toronto
4.83 out of 5 average rating, 160 reviews

Modern Eclectic Condo in King West Area

JessicaRating, 5 stars5 months ago
The location and apartment worked perfectly for our trip to Toronto. The place was clean and well maintained and everything was as described. There are lots of great restaurants and bars within walking distance but the apartment location was just far enough away to be very quiet and peaceful.
Guest favourite
Cottage in Kawartha Lakes
4.9 out of 5 average rating, 117 reviews

1950's Romantic & Whimsical cottage on Gull River

JulieRating, 5 stars5 months ago
Beautiful place! Can’t wait to return. The fishing is fantastic here! Thank you so much Stephanie you are a fantastic host !!!
Superhost
Home in Barrie
4.81 out of 5 average rating, 248 reviews

Entire House w/ Games Room-by Ski Hills & Downtown

VyomRating, 5 stars2 weeks ago
We stayed here during Snowmaggedon' 25 and the cozy place made it more enjoyable. We even got stuck twice due to lot of snow, but the neighbors in the area were very helpful and it just became another fun snow activity. Location is close to the good snow resorts in area and offers a lot of activities to do. The place was clean and pet friendly. All of us and the our pup had a great weekend. Highly recommended for ski/snow sport getaways.
Guest favourite
Home in Richmond Hill
4.88 out of 5 average rating, 147 reviews

Luxury 5 beds, 6 Baths custom home

舒婷Rating, 5 stars3 weeks ago
My family and I had a wonderful vacation here!The house is beautiful!
Guest favourite
Tiny home in Schomberg
4.99 out of 5 average rating, 203 reviews

SNAKE CABIN(rustic, 'off-the-grid')

MahdiRating, 5 stars3 months ago
We had a fantastic stay at this cozy cabin! The space was beautifully maintained, clean, and perfectly equipped with everything we needed for a comfortable getaway. The peaceful surroundings made it the ideal spot to relax and unwind, with stunning views that were even better than the photos. The host was incredibly friendly and responsive, ensuring a seamless experience from start to finish. I can’t recommend this cabin enough and would absolutely love to return for another stay!
Guest favourite
Guest suite in Toronto
4.88 out of 5 average rating, 226 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

MarkRating, 5 stars2 months ago
Perfect home-base during a holiday visit with family nearby.

Family-friendly home rentals with a pool

Superhost
Condo in Downtown Toronto
4.68 out of 5 average rating, 68 reviews

Bright Condo in the Entertainment District.

MargauxRating, 5 stars3 months ago
The most appreciated in this apartment was tranquility, even if it is in a big city you could not hear anything around either neighbors or outside, very peaceful, the apartment was very clean, everything we needed was there, the value for money is perfect. In addition, Fabio was responsive to our questions and very pleasant. I would highly recommend this listing.
Superhost
Apartment in Toronto
4.9 out of 5 average rating, 58 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars1 week ago
Really amazing view and building in a great location with easy access to GO trains and TTC. Building facilities are great! Check out is 10am
Guest favourite
Cabin in Mono
4.95 out of 5 average rating, 299 reviews

The Trails Retreat (Private Cabin)

LillyRating, 5 stars2 weeks ago
We had the most peaceful stay, we were arriving in a snow storm and Jill was just a fantastic host! She ensured to shovel clear paths for us and ensured we had what we needed. The cottage was the perfect spot to relax and be cozy. Thank you so much for having us!
Superhost
Condo in Downtown Toronto
4.67 out of 5 average rating, 374 reviews

Modern Condo in the heart Downtown Toronto!

朱音Rating, 5 stars2 months ago
Good location good room good host. He accepted our request a lot. Thank you so much!
Guest favourite
Condo in Downtown Toronto
4.97 out of 5 average rating, 236 reviews

Chic, High-Rise Apartment with CN Tower Views

SheaRating, 5 stars3 months ago
We had an excellent stay at Virginia’s place! Four of us came to Toronto for a concert at the Rodger’s Centre which was just across the street. The unit was quite a bit bigger than I expected! There was plenty of room for all four of us, we never felt crowded. We were able to walk to a huge variety of restaurants and activities. Virginia was beyond kind and welcoming. Super quick to respond and easy to communicate with! I would highly recommend staying with Virginia to anyone coming to Toronto!
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 296 reviews

King West Victorian Studio Gem

JanetRating, 5 stars3 months ago
Everything was perfect from the get go!!Kathleen is super responsive and professional, going above and beyond! I felt right at home as soon as I stepped into the Airbnb! It was cozy and it had everything I needed and more! I can’t wait to return!
Guest favourite
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars8 months ago
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!
Superhost
Condo in Downtown Toronto
4.76 out of 5 average rating, 354 reviews

Airbnb Friendly- Sleeps 6 With FreeParking!

GwenRating, 5 stars4 days ago
Great location and apartment! Super convenient. We stayed long term, and had a few maintenance requests over the few months we were here, and the Property Manager was extremely responsive and on top of everything.

Quick stats about holiday rentals that are family-friendly in East Gwillimbury

  • Total rentals

    90 properties

  • Nightly prices starting at

    $16 AUD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 properties include access to Wi-Fi

Destinations to explore