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Family-friendly vacation rentals in Oakville

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oakville family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Guest suite in Orangeville
4.92 out of 5 average rating, 771 reviews

Hot Tub & Pool Getaway - Headwaters Retreat

TeresaRating, 5 stars4 days ago
Susan’s place was clean, well-equipped and pristine. It was indeed a beautiful retreat, complete with hot tub and a pool. Communication with her was always pleasant and accommodating. Everything was well thought-out.
Guest favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 324 reviews

Beautiful Condo + CN Tower View + Free Parking

JosieRating, 5 stars5 days ago
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.
Guest favorite
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 favorite
Condo in Downtown Toronto
4.89 out of 5 average rating, 842 reviews

1 Bedroom Suite - DT Core (Office/Bidet/Balcony)

Glen & TraceyRating, 5 stars1 week ago
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.
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 stars3 months ago
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
4.87 out of 5 average rating, 107 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

AnaïsRating, 5 stars1 week ago
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!
Guest favorite
Home in Lincoln
4.92 out of 5 average rating, 304 reviews

Amazing Lake-Front Retreat!

RachelleRating, 5 stars2 weeks ago
Beautiful home! Very spacious, great views and Nayem went out of his way to make us feel welcome. Would recommend!
Guest favorite
Condo in Downtown Toronto
4.86 out of 5 average rating, 151 reviews

Modern 1 Bdrm Suite Downtown District - Lake View

ClintonRating, 5 stars1 month ago
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

Top guest favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 299 reviews

Lively 1+1 Lakeview Condo near CN Tower + Free Prk

MalcolmRating, 5 stars5 days ago
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 !
Top guest favorite
Home in Port Dalhousie
4.95 out of 5 average rating, 287 reviews

Nautica Beach House on Lake Ontario

MaryamRating, 5 stars3 days ago
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
Top guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 159 reviews

Beautiful suite in Downtown Toronto

LesleyRating, 5 stars1 week ago
Great space for folks attending public events in the downtown area.
Top guest favorite
Home in Toronto
4.9 out of 5 average rating, 136 reviews

Charming Century Home Close to Vibrant Shops

RigoRating, 5 stars2 weeks ago
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.
Superhost
Boat in Port Dalhousie
4.9 out of 5 average rating, 130 reviews

Bob's Place Uncle

DanaRating, 5 stars2 weeks ago
We had a great stay aboard Bob’s Yer Uncle! Very well organized and well stocked with all the necessities, and super clear instructions on getting into the marina and marina washrooms/showers - which we used instead of the boat shower. Would recommend visitors bring their own water for drinking. We’re hoping to book again the next time we’re in St. Catharines!
Guest favorite
Home in Richmond Hill
4.89 out of 5 average rating, 157 reviews

Luxury 5 beds, 6 Baths custom home

StephenRating, 5 stars3 days ago
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!
Guest favorite
Guest suite in Toronto
4.89 out of 5 average rating, 240 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

RachelRating, 5 stars1 week ago
I stayed here with my family for two nights while visiting the city! The space was super nice and welcoming. Spotless, updated, and comfortable. About a 10min walk to transit but straight forward and the neighbourhood felt very safe.
Guest favorite
Condo in Downtown Toronto
4.92 out of 5 average rating, 240 reviews

Vibrant downtown place

LeandroRating, 5 stars3 weeks ago
The apartment is very nice and clean, located in a great area with plenty of shops and restaurants nearby. It's also equipped with everything you need for a short or long stay. Alexandru is very friendly and made sure everything was impeccable.

Family-friendly home rentals with a pool

Top guest favorite
Guest suite in Thorold
4.97 out of 5 average rating, 211 reviews

Niagara Bike Trails, Golfing, Wineries

RebecaRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Toronto
4.9 out of 5 average rating, 59 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars4 months 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
Superhost
Condo in Downtown Toronto
4.67 out of 5 average rating, 379 reviews

Modern Condo in the heart Downtown Toronto!

FelipeRating, 5 stars5 days ago
I had a wonderful stay at Jonathan’s apartment in Toronto. From the moment I arrived, he was incredibly attentive and made sure everything was perfect. The apartment is in an excellent location — right in the heart of the city, with a stunning view facing the CN Tower. Waking up to that view every morning was truly unforgettable. I highly recommend this place to anyone traveling to Toronto. It’s the perfect spot for a comfortable and memorable stay!
Superhost
Home in St. Catharines
4.83 out of 5 average rating, 247 reviews

Stunning Large Family home

AlettaRating, 5 stars3 weeks ago
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.
Guest favorite
Bungalow in Milton
4.91 out of 5 average rating, 35 reviews

Milton Home- a Family Oasis

SherryRating, 5 stars9 months ago
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
Superhost
Guesthouse in Bronte West
4.6 out of 5 average rating, 10 reviews

*Cozy&Chic LL 2Bed 2Bath-Kitchenette l *Near LAKE*

JulieRating, 5 stars5 months ago
A truly intimate and comfortable internet spot perfect for a vacation
Top guest favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 245 reviews

Chic, High-Rise Apartment with CN Tower Views

KevinRating, 5 stars2 weeks ago
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.
Guest favorite
Home in Niagara-on-the-Lake
4.79 out of 5 average rating, 230 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

ChandraRating, 5 stars3 weeks ago
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!

Quick stats about vacation rentals that are family-friendly in Oakville

  • Total rentals

    460 properties

  • Nightly prices starting at

    G$2,091 GYD before taxes and fees

  • Total number of reviews

    7.4K reviews

  • Pet-friendly rentals

    150 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

Destinations to explore