
Family-friendly holiday rentals in Milton
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Top-rated family-friendly rentals in Milton
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Popular amenities for Milton family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Condo + CN Tower View + Free Parking
A few days in Toronto watching some baseball. Perfect location, 5 minute walk, view of the CN Tower from the balcony. Very spacious for 4 adults and two grown teenagers. Everything we required in the accommodation. Very easy check in and parking. Excellent, prompt communication from Katherine. Will definitely stay here again.

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!

1 Bedroom Suite - DT Core (Office/Bidet/Balcony)
Wow and thank you. To find such a perfect location was so fortunate. Cal sent a warm and welcoming message that just set the experience off to a great start. The condo was clean and modern and just felt so comfortable. There is something energizing about being right in the centre of thing’s, especially when you have such a wonderful space to come “home” to. Thanks to Cal for providing such a terrific space.

Luxury heart of downtown by CN Tower/ MTCC/Union
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 !

Casa Di Mama | Beautiful 2BR Downtown-Free Parking
We had a great weekend in Toronto. The location is perfect, 10 min walk from the Rodger center. The condo is great, easy check in!

Cosy Updated Lakefront Cottage
Robert’s cabin was perfect! We loved it so much that we would consider making another trip from where we live in Seattle just to stay here again. It was so clean and had everything we could want. I just love the vision they had when decorating their space. It was so beautiful. The hot tub was very spacious, we used the gas grill and it worked perfectly, wood was available for a fire, we used their cute seadoo pedal boat, which was so fun! Plenty of kayaks were available. The lake was a dream. We didn’t get to fish but there must be a lot of fish in there because they were constantly jumping out of the water. There were comfy seats all over the yard and a lovely gazebo. The inside was so cozy. Mattress was perfect. I could go on and on about all the things we loved but I’ll just say 10/10 recommend :)

Amazing Lake-Front Retreat!
Beautiful home! Very spacious, great views and Nayem went out of his way to make us feel welcome. Would recommend!

Modern 1 Bdrm Suite Downtown District - Lake View
Beautiful apartment within walking distance to everything you need. Host was accommodating and responded quickly to inquiries. Apartment was spotless. Was easy to find and check-in was easy. Would stay here again.
Family- and pet-friendly home rentals

Lively 1+1 Lakeview Condo near CN Tower + Free Prk
Mehrdads condo was perfect for us. The view from the balcony, the proximity for bars and restaurants the CN tower and aquarium. Ten minute walk to union street train station. The condo was comfortable and well furnished and we felt very settled as soon as we moved in. Communication and entry on arrival was hassle free. Would totally recommend !

Nautica Beach House on Lake Ontario
Absolutely loved this stay. Beautiful details, cool decor and a stunning location with a beautiful view and a two minute walk to the beach. All necessary amenities available, and host was very responsive throughout stay. Definitely recommend this stay if you’re looking for peaceful evenings while being so close to Niagara on the lake to enjoy the wineries. Can’t wait to visit again

Cozy one bedroom apartment in Roncesvales village
The location of this apartment is fabulous. Easy to get from the airport and to get into the centre of Toronto. There is a big supermarket and liquor store a few minutes walk away and many restaurants, cafes and bars. High park is a short walk and the surrounding roads are very pretty. The bed in the apartment is comfortable, the shower is great. It’s quiet at night and easy to sleep.

Country Cabin Escape | King Bed | Pet Friendly
We had a great time and all facilities we needed to make the weekend getaway worth it. We could barbecue, use the fully equipped kitchen, and walk around in the serene surroundings of the cabin. It was picture perfect, fresh air - almost made me want to leave cities and settle in a place like that. Thom and Lisa were very responsive and made everything comfortable.

Charming Century Home Close to Vibrant Shops
Beyond the house itself, the hosts were truly outstanding. They were not only extremely courteous but also incredibly responsive to any questions we had, making us feel welcomed and well-cared for throughout our entire stay. Their genuine hospitality added significantly to the positive experience. If you're looking for a unique and memorable stay in Toronto, especially if you appreciate the charm of a well-preserved historic home combined with the warmth of exceptional hosts, look no further. We highly recommend this house.

Cozy Rustic Cabin in Wine Country
My dog and I had the most amazing staycation at Joe's cabin and I don't know who enjoyed it more - me or him! The location is beautiful - so peaceful and so green and lush. The cabin has everything you need and is centrally located to many wineries and easy to get to Niagara-on-the-Lake or surrounding areas. Joe and Emma are super friendly and helpful and we hope to return again next year!

Centrally located - beautiful one bedroom apt.
This was a perfect place for us to stay during our trip to the area. We were able to cook a full meal in the kitchen and had no issues with any of the amenities.

Luxury 5 beds, 6 Baths custom home
Perfect spot for a group trip. Quiet neighborhood, close to the TTC for easy access to downtown. Jay was awesome at handling our request to drop off our luggage prior to our scheduled check-in time. Would definitely stay again!
Family-friendly home rentals with a pool

Niagara Bike Trails, Golfing, Wineries
I usually do not leave reviews but this place deserves it. We (husband & 2 corgis included) really enjoyed our stayed. Check-in was easy and Sonia was great to communicate with. The surroundings are beautiful and peaceful. Close (10 - 15 min) to stores if needed and to the Falls. Great place to relax after a long day of walking around. The hosts are super nice people and we wouldn't hesitate to book again once you come back.

The Trails Retreat (Private Cabin)
10 STAR!!! Amazing property! Impeccably maintained gorgeous cabin (rustic/modern and very classy) and surrounding grounds. So lovely! The hosts have thought of absolutely everything. I didn't want to leave! Now on my bucket list to return, hike Mono Cliffs then relax by the sparling clean pool. The Trails Retreat Cabin is an affordable deluxe property that you really should treat yourself to!

Stunning Large Family home
Went for a weekend away and the place was a great stay. It was clean and communication was great. They even left us snacks and a nice note.

Your Peaceful Santuary in Nature
Would highly recommend! A very spacious spot with lots of activities and lovely surroundings. The place is very cozy with the wood burning stove and plethora of candles. Annette was very pleasant, responsive and accommodating! We had a great time playing with her dogs in the snow. We will be back!

Milton Home- a Family Oasis
This place was absolutely amazing. It had everything you could possibly need and want. We enjoyed everything- the qames, pool table and darts. We wish we hadn't planned so much so we could make better use of everything. Thomas was very responsive and went out of his way to help when there was something we couldn't figure out. We loved being there and will definitely look to return if we return to Toronto

Chic, High-Rise Apartment with CN Tower Views
We were in town to attend a couple Jays games and see DT Toronto. This location was great for both. Also easy access to Union station. Condo was just right for us.

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool
Beautiful place. The hosts were so kind and helpful. The area is safe and so close to the outlets which was a huge plus for us ladies! Hope to stay there again one day!

Sunny Pines Farm Studio Tennis Court/Bruce Trail
This property is absolutely beautiful! We had the best time playing tennis and basketball, going in the pool and sauna. The pool is cool which was so nice after getting super hot in the sauna. 10/10 recommend. The inside was beautiful and relaxing, felt like a perfect getaway and we will be back for sure! Thank you for sharing your home!
Quick stats about holiday rentals that are family-friendly in Milton
Total rentals
540 properties
Nightly prices starting at
₹1,720 before taxes and fees
Total number of reviews
10K reviews
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
380 properties have a dedicated workspace
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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
- BMO Field
- Massey Hall
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Casa Loma
- Dufferin Grove Park
- Jackson-Triggs Niagara Estate
- Royal Woodbine Golf Club
- Royal Ontario Museum
- Royal Botanical Gardens