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Family-friendly vacation rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Orangeville family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cottage in Kimberley
4.86 out of 5 average rating, 338 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

AustinRating, 5 stars1 month ago
Thank you for the wonderful stay! Our group loved our stay! Would highly recommend.
Top guest favorite
This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.
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
A modern living room is shown with large floor-to-ceiling windows allowing ample natural light. A comfortable gray sofa and a dark gray couch provide seating, while a stylish coffee table is centered on a patterned area rug. A flat-screen television is positioned on a white media console.
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
A modern bathroom features a sleek, white sink atop a glass counter. Dark wooden cabinetry provides storage, while light-colored tiles contribute to a clean, contemporary look. Essential amenities, such as hand soap and rolled towels, are visible, ensuring a functional space.
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
An outdoor balcony space is shown, featuring a gas grill and a set of metal chairs and tables. Paver stones create a clean surface. A small green area adds natural elements, while a skyline view is visible in the distance.
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
A comfortable living area features a light grey sofa adorned with several cushions, complemented by a dark ottoman. Sunlight enters through large windows, offering views of the outdoor space. A small dining table for four is positioned nearby.
Condo in Downtown Toronto
4.86 out of 5 average rating, 101 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

JordanRating, 5 stars3 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
A room featuring a foosball table and hardwood flooring is illuminated by natural light from a nearby window. The window is framed by dark curtains, and a wooden door leads to another area of the home. Vintage woodwork and a decorative mirror add character.
Home in Kimberley
4.88 out of 5 average rating, 198 reviews

Heart of Kimberley - with views and a hot tub

RobinRating, 5 stars4 days ago
Great gals weekend. We really enjoyed the General Store and exploring the area. The house linens were great, beds comfy and the seating areas too :) Weather wasn't conducive to using the outdoor spaces and as older folks we didn't think we'd manage the step stool to get into the hot tub. If there's a next time, we'll try the bustling "Justin's Oven" !!
Guest favorite
A rustic cabin sits among lush greenery, featuring a wrap-around deck and large windows that invite natural light. The structure blends into the landscape, providing a serene escape surrounded by trees and open spaces.
Chalet in Priceville
4.91 out of 5 average rating, 469 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

AndrewRating, 5 stars2 months ago
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.

Family- and pet-friendly home rentals

Guest favorite
A well-appointed bedroom features a spacious bed adorned with neatly arranged white towels. A decorative throw enhances the bedding, while bedside lamps provide soft illumination. An exercise bike is positioned near the bed, and a tree-like light fixture adds a unique touch to the ambiance.
Home in Roncesvalles Village
4.92 out of 5 average rating, 152 reviews

Cozy one bedroom apartment in Roncesvales village

LouRating, 5 stars1 week ago
Looked just like the pictures, the location was amazing! So close to the GO, UP express and subway line, Roncy is right there, and it's about 50meters from Bandit Brewery! Seher was responsive and accommodated a different check in time due to our flight being a bit later, met us and gave us the tour of the place and explained entry! Would stay again
Guest favorite
A cozy living area features a light-filled space with a large, neutral-colored sofa adorned with patterned cushions. Two accent chairs with geometric patterns complement a white coffee table, while a dining table is visible in the background near a modern kitchen area.
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
An open-concept living space features a leather couch and an armchair, with a coffee table positioned nearby. A light wood kitchen island provides seating with two yellow stools. Natural light enters through two windows, illuminating the modern decor and warm wood flooring.
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!
Superhost
The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.
Home in Barrie
4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

DavidRating, 5 stars3 weeks ago
Great place, will stay again
Top guest favorite
A round glass table is accompanied by two white chairs, positioned in a bright corner by the window. A tall lamp stands beside the table, and a vase with flowers adds a touch of color to the neutral gray walls.
Home in Guelph
4.96 out of 5 average rating, 149 reviews

Heritage Home (4+ Bedrooms) near Downtown Guelph

BradRating, 5 stars1 week 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
Home in Richmond Hill
4.89 out of 5 average rating, 154 reviews

Luxury 5 beds, 6 Baths custom home

PeterRating, 5 stars3 days ago
Loved the place. We were a party of 10 here to celebrate a 100th bday. It met everyones needs/expectations.
Top guest favorite
A rural landscape features a gravel driveway leading to a spacious barn-style cabin, surrounded by tall evergreen trees. A road sign indicating a speed limit of 60 km/h is visible at the edge of the road, showcasing a tranquil countryside setting.
Tiny home in Schomberg
4.99 out of 5 average rating, 205 reviews

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

MattRating, 5 stars1 month ago
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!
Guest favorite
A living room features a gray sofa accented with decorative cushions, paired with two mid-century modern chairs. A large window allows natural light to illuminate the space. A mounted flat-screen TV and an electric fireplace are visible, enhancing the cozy atmosphere.
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

Superhost
A bright living room area features a comfortable seating arrangement with a mix of chairs and a couch. A large television is mounted on the wall, and a decorative painting of a bird enhances the space. Natural light enters through large windows, creating a welcoming environment.
Apartment in Toronto
4.9 out of 5 average rating, 59 reviews

New condo w/ gorgeous lake views

ConorRating, 5 stars2 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
Guest favorite
A modern open-concept living space features a sleek kitchen island with a cooktop, surrounded by contemporary bar stools. A cozy seating area includes a sectional sofa and armchairs, arranged around a stylish fireplace, with large windows allowing natural light to brighten the room.
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!
Guest favorite
A clear view of the heated swimming pool is presented, surrounded by a well-manicured lawn. Two lounge chairs are positioned beside the pool, offering a relaxing space. Lush greenery and trees create a natural backdrop, enhancing the serene atmosphere of the outdoor area.
Cabin in Mono
4.95 out of 5 average rating, 304 reviews

The Trails Retreat (Private Cabin)

JodieRating, 5 stars3 days ago
This little place is one of a kind!! Would return in a heart beat. Friendly and responsive host, beautiful, peaceful setting, Hiking and archery on property. The house itself was clean, cozy, and private . We enjoyed our stay so much!! Will definitely come again!
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
A truly intimate and comfortable internet spot perfect for a vacation
Guest favorite
A playground is surrounded by a wooden fence, featuring colorful equipment under green canopies. Various structures include slides, climbing features, and swings. A soft surface of wood chips surrounds the play area, with a paved path nearby and benches for seating.
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
A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.
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
A spacious outdoor deck is furnished with a modern seating area and a dining table, surrounded by lush greenery. A sculptural horse figure stands nearby, while a scenic view of open fields and a distant structure completes the tranquil country setting.
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars3 weeks ago
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.
Guest favorite
An indoor swimming pool is set within a sleek environment, featuring a clear water surface reflecting the light from overhead fixtures. The pool area includes decorative mosaic accents on the edges and two stainless steel ladders for entry.
Condo in Mississauga
4.84 out of 5 average rating, 58 reviews

2 Bedroom Condo Near Square One with Massage Chair

maudeRating, 5 stars3 days ago
Very nice stay at Bose and Esther's. Thanks again!

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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