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Family-friendly holiday 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 favourite
Guest suite in Orangeville
4.92 out of 5 average rating, 769 reviews

HotTub & Pool Getaway - Headwaters Retreat

JohnnyRating, 5 stars6 days ago
We had a wonderful experience at this Airbnb! The home was exactly as described clean, spacious, and well equipped for a comfortable stay. The theatre room was a great bonus and made for some really fun evenings. The location was convenient, and everything we needed was provided, from fresh linens to kitchen essentials. Communication with the host was smooth and timely, and check-in was easy. We appreciated the thoughtful touches throughout the space that made it feel like a home away from home. Would definitely stay here again thank you for a great visit!
Guest favourite
Apartment in Downtown Toronto
4.97 out of 5 average rating, 323 reviews

Beautiful Condo + CN Tower View + Free Parking

JosieRating, 5 stars2 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 favourite
Apartment 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
Apartment in Downtown Toronto
4.89 out of 5 average rating, 842 reviews

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

Glen & TraceyRating, 5 stars4 days 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
Apartment 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
Apartment 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 favourite
Home in Lincoln
4.92 out of 5 average rating, 304 reviews

Amazing Lake-Front Retreat!

RachelleRating, 5 stars1 week ago
Beautiful home! Very spacious, great views and Nayem went out of his way to make us feel welcome. Would recommend!
Guest favourite
Apartment 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

Guest favourite
Flat in Hamilton Beach
4.95 out of 5 average rating, 42 reviews

The Beach House apartment Lake front Second floor.

JanetRating, 5 stars5 months ago
Wonderful, quirky place full of art with fantastic lake views. Eric was super friendly and responsive and gave us a great recommendation for breakfast!
Top guest favourite
Home in Port Dalhousie
4.95 out of 5 average rating, 287 reviews

Nautica Beach House on Lake Ontario

MaryamRating, 5 starstoday
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 favourite
Apartment in Downtown Toronto
4.93 out of 5 average rating, 158 reviews

Beautiful suite in Downtown Toronto

ChloeRating, 5 stars3 weeks ago
10/10 perfect Air BnB, will most definitely book again next time we go down (especially for a concert), it was literally right across the street from the Roger’s Center which is where our Post Malone concert was. Oron is super descriptive on the process to check in/out and how to find parking, which as someone with OCD this was a blessing. Anything I needed or had questions about he literally answered within 5min! Also you literally get a view of the beautiful CN tower… jaw dropping! Bonus: that bed is hella comfy!!!
Top guest favourite
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.
Guest favourite
Guest house in Lincoln
4.81 out of 5 average rating, 429 reviews

Cozy Rustic Cabin in Wine Country

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

Bob's Yer 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 favourite
Home in Richmond Hill
4.89 out of 5 average rating, 156 reviews

Luxury 5 beds, 6 Baths custom home

PaulineRating, 5 stars1 month ago
An amazing home meeting the needs of our multi-generational family spending a week together in the GTA to cheer on our daughter participating in a National sporting event. Listing is reflective of the gorgeous, clean home. We would definitely look to return should another opportunity present!
Guest favourite
Guest suite in Toronto
4.89 out of 5 average rating, 239 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.

Family-friendly home rentals with a pool

Top guest favourite
Guest suite in Thorold
4.97 out of 5 average rating, 210 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
Flat in Toronto
4.9 out of 5 average rating, 59 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars3 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
Apartment in Downtown Toronto
4.67 out of 5 average rating, 377 reviews

Modern Condo in the heart Downtown Toronto!

NicoleRating, 5 stars2 weeks ago
Myself and 2 friends enjoyed our 3 night stay to the fullest! Location was amazing! Jonathan was extremely responsive. Bed was very comfortable. Pull out bed not so comfy but was to be expected. Lots of feminine products under the sink for guests to use in including salon style hairspray. Roof top pool was amazing and not too busy! Would highly recommend Jonathan's place!
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 favourite
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
Guest house 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 favourite
Apartment 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 favourite
Home in Grimsby
4.94 out of 5 average rating, 31 reviews

Niagara Wine Country Retreat - Sauna/spa/salt pool

TraceyRating, 5 stars6 days ago
My family had a wonderful time celebrating my Granddaughter’s 10th birthday, as well as Father’s Day. Nancy was a wonderful host who greeted us with her family, for a tour of the property upon check-in. The property is exceptionally beautiful with so much to do for everyone so was there never a reason to leave but it was great having the town of Grimsby only a 5 min drive away and the Bruce trail right next door. We had such a wonderful time and will definitely look to book again in the future.

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

  • Total rentals

    460 properties

  • Nightly prices starting at

    ₹865 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

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