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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

Top guest favorite
Guest suite in Orangeville
4.92 out of 5 average rating, 754 reviews

HotTub & Cozy Getaway - Headwaters Retreat

AakashRating, 5 stars1 day ago
Beautiful place, very close to town. All needs taken care of, didn't feel like anything was missing. I wish I could've stayed for longer
Guest favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 317 reviews

Beautiful Condo + CN Tower View + Free Parking

DylanRating, 5 stars4 days ago
the check in instructions were extremely thorough and 100% accurate. checked into the condo building with no problems what so ever. 4 of us had plenty of room to sleep. amazing location near the rogers centre, can see it from the patio. all the bedding and laundry was clean and ready for use. fully functional kitchen. the entire place was pristine. Great location for any concerts or other events. Will definitely be staying here again!
Guest favorite
Condo in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars2 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!
Superhost
Farm stay in Pelham
4.94 out of 5 average rating, 96 reviews

Pine Creek Acres Country Retreat

PriyaRating, 5 stars8 months ago
Loved this home, it was beautifully decorated every inch. My favourite bedroom was the one on the first floor. This was a change from the typical waterfront properties our family books but with a heated pool and jacuzzi that was situated in a landscaped backyard we couldn’t ask for more. Very clean and she had everything. Lindy has really outdone herself to make sure her guests from all ages enjoy her home. She accommodated our family literally 3 hours before checkin, as the cottage we originally booked the host cancelled less than 24hrs before checkin. Thank you Lindy for sharing your home!!
Guest favorite
Condo in Downtown Toronto
4.89 out of 5 average rating, 837 reviews

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

JulieRating, 5 stars4 days ago
Always a great host and a 2 minute walk to the Roger's Stadium......can't go wrong!
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 stars1 month 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
4.86 out of 5 average rating, 101 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

JordanRating, 5 stars4 days ago
If I ever have another event at the Rogers Centre or anything nearby I will absolutely be checking to see if this space is available. As someone who never has driven in Toronto Julian's easy to follow instructions made it a breeze, & the parking in the secure parking garage made us feel all the better. Julian was so understanding for our arrival & helped us every step of the way. The fact I was able to walk to both of my concerts & be in my seat within half an hour of leaving this apartment was outstanding. Thank you so much Julian, you have a repeat customer for sure!
Guest favorite
Guest suite in Hamilton
4.96 out of 5 average rating, 70 reviews

Holliday Oasis w/ Hot Tub

IsabelleRating, 5 stars2 months ago
Me and my man came here for Valentine’s Day’s and had a really nice time. The hot tub was a nice experience. The place was nice, clean and organized. Holly even got us a valentines card and chocolates which was so nice. Will definitely book again when it’s hot outside.

Family- and pet-friendly home rentals

Guest favorite
Home in Roncesvalles Village
4.92 out of 5 average rating, 152 reviews

Cozy one bedroom apartment in Roncesvales village

CristinaRating, 5 stars3 weeks ago
O espaço de Seher é perfeito, ótima localização, perto de transportes públicos, comércio e restaurantes. Está bem equipado, tem tudo que um hóspede precisa e até o que não precisa. Super completo e adequado. Tudo limpo e arrumado. A anfitriã é ótima, simpática, nos recebeu muito bem e nos explicou como funciona o espaço. Gostei que tem bilhetes nos locais para nos orientar sobre o que fazer, o que não fazer, o que tem em cada armário, tudo pra facilitar nossa estadia. Como ela disse na descrição, dá para ouvir alguns barulhos do andar de cima mas nada demais, nada que atrapalhe ou incomode. Eu adorei e pretendo voltar assim que possível. Super recomendo o espaço de Seher.
Guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 155 reviews

Beautiful suite in Downtown Toronto

JessRating, 5 stars5 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 favorite
Apartment in Milton
4.72 out of 5 average rating, 157 reviews

Studio Apt in Milton Dorset Park

KaranRating, 5 stars1 month ago
Had an amazing stay at David’s place. Super responsive hosts and the place was super clean!
Top guest favorite
Home in Guelph
4.96 out of 5 average rating, 149 reviews

Heritage Home (4+ Bedrooms) near Downtown Guelph

BradRating, 5 stars2 weeks ago
My crew and myself stayed the week in comfort at Mike’s. Lots of room for everyone, beds were clean and comfortable. Close to all amenities and easy to get to.
Guest favorite
Guest suite in Hamilton
4.92 out of 5 average rating, 202 reviews

Centrally located - beautiful one bedroom apt.

LorettaRating, 5 stars2 weeks ago
We loved the cozy space up on the third floor! It was unique being in an old brick house. We were able to walk to do our planned visiting. The parking space and the electric fire place were added perks. Amanda was a great host! Would definitely stay again.
Superhost
Boat in Port Dalhousie
4.9 out of 5 average rating, 126 reviews

Bob's Yer Uncle

KristaRating, 5 stars7 months ago
The boat was the perfect size for a quick couples get-away. Watching the sunset from the bow was heaven; I didn't want to leave. An easy walk to bars and restaurants made for a perfect evening. Scott was a great host and took care to make sure we were settled in. Looking forward to a repeat visit next summer.
Guest favorite
Home in Richmond Hill
4.89 out of 5 average rating, 154 reviews

Luxury 5 beds, 6 Baths custom home

PeterRating, 5 stars4 days ago
Loved the place. We were a party of 10 here to celebrate a 100th bday. It met everyones needs/expectations.
Guest favorite
Guest suite in Toronto
4.89 out of 5 average rating, 232 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

BruceRating, 5 stars1 week ago
My hosts Lucy and Don were completely accommodating, communicative, and responsive. Coming and going was a breeze. A completely outfitted kitchen with all that you'd need. The space offers total privacy. A quiet, but lively-enough neighborhood, steps away from Yonge St. It checked off all the boxes and I'm very satisfied with the experience and my stay.

Family-friendly home rentals with a pool

Top guest favorite
Guest suite in Thorold
4.97 out of 5 average rating, 207 reviews

Niagara Bike Trails, Golfing, Wineries

KentRating, 5 stars6 months ago
This place is perfect for one or two people staying in the area and close to St. Catharines, Niagara Falls, Niagara On The Lake, and the Welland Canal. It’s clean, neat and private. Very comfortable bed & linens. Sonia and Ron are excellent hosts and took time to meet us and visit before we left. Be sure to check out their recommendations for area sites and restaurants!
Superhost
Home in St. Catharines
4.84 out of 5 average rating, 242 reviews

Stunning Large Character Family home

CatherineRating, 5 stars1 month ago
The house was easy to find. The lock was having trouble but then we were able to get in. The next day realized the lock on the house was malfunctioning and that was why we had trouble getting in. Texted the owner and someone was immediately sent to fix(replace the lock). Great customer service from the owners.
Guest favorite
Campsite in Hagersville
4.96 out of 5 average rating, 23 reviews

Tent Site #3 w/pool & shower in the Countryside.❤️

AndrewRating, 5 stars1 month ago
Gerry and Rosemary were extremely personable and my stay felt like I was with family. They were also very helpful and communicated quickly. I could not recommend them more if you are looking for a quiet and relaxing stay!!!
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 stars3 months ago
Une place vraiment internet intime et comfortable parfait pour une vacance
Guest favorite
Bungalow in Milton
4.91 out of 5 average rating, 34 reviews

Milton Home- a Family Oasis

SherryRating, 5 stars8 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
Guest favorite
Condo in Downtown Toronto
4.97 out of 5 average rating, 237 reviews

Chic, High-Rise Apartment with CN Tower Views

SheaRating, 5 stars5 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 favorite
Home in Niagara-on-the-Lake
4.78 out of 5 average rating, 227 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

JasonRating, 5 stars8 months ago
Beautiful, peaceful home with extremely comfortable and large beds. It's obvious that hosts take a great deal of pride in the property which has everything one could need. Excellent base to visit the Falls, Niagara on the Lake and the outlets. Walking distance to the Royal Niagara Golf Course (where you can hire clubs). Last but not least an amazing pool too.
Guest favorite
Home in Niagara
4.91 out of 5 average rating, 302 reviews

King West Victorian Studio Gem

JoelRating, 5 stars6 days ago
Kathleen's place was great, exactly as advertised. I really appreciated how tidy and well stocked the suite was. A great place to stay.

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

  • Total rentals

    460 properties

  • Nightly prices starting at

    ﺩ.ﺇ37 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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