Family-friendly vacation rentals in Caledon

Guesthouse in Orangeville

A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.

4.95 out of 5 average rating, 141 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Guest suite in Orangeville

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.

4.92 out of 5 average rating, 833 reviews

HotTub & Cozy Fireplace - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Tiny home in The Junction

A scenic winter view captures the path leading to the Bunkie, framed by snow-covered ground and bare trees. A tranquil sunset paints the sky in shades of pink and orange, while a stone fire pit is visible beside a wooden bench and rustic fencing.

4.99 out of 5 average rating, 193 reviews

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

Guesthouse in Halton Hills

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

4.92 out of 5 average rating, 169 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of Glen Williams &Terra Cotta, &the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay. You WILL hear wildlife and farm animals here.

4.86 out of 5 average rating, 192 reviews

Home in Caledon

Studio Apartment

Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

4.94 out of 5 average rating, 194 reviews

The historic log cabin from the 1850s is surrounded by lush greenery. A covered porch with wooden beams invites relaxation, while hanging flower baskets add subtle color. The peaked roof and wooden siding emphasize the cabin's rustic charm in a serene forest setting.

Cabin in Erin

1850 Settler's Cabin in Private Forest

Our beautiful 1850 settler's log cabin is simply furnished and does not have plumbing. Electricity is powered by a honda generator. Fresh drinking water is supplied. Bathroom is a clean, private outhouse and guests have access to our centralized guest shower facility on premises from 6-9 am/pm daily. As your Bed and Breakfast host we will personally greet you and check you in and always remain on property while offering you privacy. We are designed for a quiet, peaceful rustic getaway.

4.98 out of 5 average rating, 157 reviews

A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.

Loft in Mono

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

4.78 out of 5 average rating, 111 reviews

A brick exterior home is set against a bright blue sky, featuring a manicured front lawn with green grass and white flowers. Large windows allow natural light to illuminate the entrance, where a welcoming white door is positioned. A tree provides shade, enhancing the outdoor space.

Home in Georgetown

Halton Hills Hideaway_Private Suite

🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

4.97 out of 5 average rating, 145 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

4.95 out of 5 average rating, 235 reviews

The spacious bedroom features a king bed with a striped blanket and a decorative area rug. Large windows allow natural light, which brightens the neutral walls. French doors lead to an outdoor area, complemented by a seating arrangement and a wooden furniture set.

Place to stay in Mono

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville. We have three active dogs who often demand attention! Can be arranged as a two bedroom with privacy or a one bedroom with extra room. King bed in the large bedroom. Double futon in the sitting room. Fabulous bathroom with views. The guest house is 70 feet from main house. Quiet, nice forest walks. NOT a 'corporate Airbnb' - managed by owner. Near Bruce Trail and Hockley.

Dome in Aldershot Central

4.96 out of 5 average rating, 199 reviews

Winter Escape Tropical Dome! Animal Lovers Dream

Jungle Dome on a farm in Burlington! Enjoy a tropical stay in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Sleeps 4. Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed to be a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can feed and interact with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Guest suite in Orangeville

A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.

5 out of 5 average rating, 187 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

Popular amenities for Caledon family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 108 reviews

A dining area is featured with a round table surrounded by four sleek chairs. A patterned wallpaper adds texture, while a rack displays hanging clothing. The kitchen includes a wooden countertop and modern appliances, complemented by natural light from nearby windows.

Guest suite in Elora

The Carlton Elora | Cozy Retreat with Hot Tub

4.92 out of 5 average rating, 929 reviews

The studio apartment features a bright and open layout with wooden flooring. A kitchenette is visible in one corner, equipped with shelves and a coffee station. A queen size bed is positioned next to a decorative partition, enhancing the separation of spaces.

Loft in Guelph

Light and airy studio loft

4.98 out of 5 average rating, 165 reviews

A modern living area features a large, dark sectional sofa adorned with blue and orange cushions. A floral area rug adds a splash of color beneath the furniture. Natural light enters through two windows, and a mirror reflects the space, enhancing the open feel.

Home in Orangeville

Hot Tub & Private Suite - Casa Facciolo

Farm stay in Township Of Southgate

An industrial-style apartment features a spacious open living area with a dark leather couch and a wooden coffee table. A staircase leads to an upper sleeping area, while concrete walls provide a modern backdrop. Natural light enters from nearby windows, enhancing the interior space.

4.86 out of 5 average rating, 190 reviews

Loft Where City Meets Country With Hot Tub

4.94 out of 5 average rating, 167 reviews

The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.

Cabin in Innisfil

Lakefront Cozy Cottage w Hot Tub!

4.94 out of 5 average rating, 162 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

4.96 out of 5 average rating, 164 reviews

The modern kitchen and living area feature sleek white cabinetry and stainless steel appliances. A light-toned island with seating is positioned near a comfortable sofa, which is complemented by decorative pillows. Soft lighting enhances the inviting atmosphere of this open-concept space.

Apartment in Windfields

Family Friendly | HOT TUB | Near Toronto & UOIT

Guest suite in Cedar Hill

A single-story garden suite is showcased amidst lush greenery. The exterior features a grey facade, large windows, and dual front doors. A wooden deck leads to the entrance, while a stone path and patio furniture are visible. Trees provide natural shade around the area.

4.92 out of 5 average rating, 243 reviews

Outdoor Hot Tub Bliss: 2Bed/2Bath Garden Suite DTK

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 159 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny home in MONO

Whispering Pines Cabin in Woodland Acres

Apartment in Horning's Mills

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

4.96 out of 5 average rating, 321 reviews

Beautiful Riverside Country Apartment

4.87 out of 5 average rating, 109 reviews

An open-concept living area features a cozy sectional sofa and a coffee table. A wall-mounted TV is positioned above a contemporary fireplace. Natural light is welcomed through sliding glass doors that lead to a private outdoor space, offering a sense of comfort and relaxation.

Apartment in Hamilton

Frenchman’s Pass - Cozy nook on the Hamilton brow

Guesthouse in Orangeville

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

4.96 out of 5 average rating, 380 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

4.94 out of 5 average rating, 101 reviews

An open living area features a cozy seating arrangement with a sofa and a day bed, which can extend to a king bed. A modern kitchen with sleek cabinetry is visible alongside a small dining table. A fireplace adds an element of warmth to the space.

Bungalow in Georgetown

Modern Stay • Prime Location • Double Parking

5 out of 5 average rating, 216 reviews

A spacious living area features a comfortable grey sectional sofa and two blue chairs. A wooden dining table with brown chairs occupies one side, while a fireplace with a wooden mantle serves as a focal point. Natural light enters through multiple windows.

Guesthouse in Brantford

The Pines, charming retreat close to the highway

4.94 out of 5 average rating, 255 reviews

A spacious living area features a white leather sectional sofa and a circular coffee table on a light rug. The wooden ceiling and walls add warmth, while a staircase leads to an upper level. A dining area is visible in the background, alongside a rustic table.

Cabin in Cambridge

Forest Hideaway

4.91 out of 5 average rating, 149 reviews

A cozy cabin interior features wooden walls and a lofted sleeping area with a patterned mattress. A black futon is positioned on the ground floor, complemented by a textured area rug. A compact kitchenette area is present, along with a sleek electric heater.

Tiny home in Erin

Bright and Cozy Tiny Pine House

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 104 reviews

Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.

Farm stay in Caledonia

Alpaca farm stay and bunkie getaway.

4.86 out of 5 average rating, 202 reviews

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Condo in Mississauga

Beautiful Penthouse with Breathtaking View

4.95 out of 5 average rating, 337 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

Cabin in Mono

The Trails Retreat (Private Cabin)

Apartment in Oakwood Village

A spacious living room is presented with a neutral-colored sectional sofa adorned with yellow accent pillows. A small glass side table complements the seating area, while a patterned area rug adds texture to the floor. Natural light enters through a window placed above the sofa.

4.84 out of 5 average rating, 108 reviews

Bright, spacious luxury basement apartment

4.88 out of 5 average rating, 115 reviews

A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.

Apartment in Mississauga

Condo in Heart of Mississauga

Condo in Humber Bay Shores

A modern living area is featured, showcasing a white sofa adorned with colorful pillows. A round coffee table is centered in front of a wall-mounted TV. Large sliding doors open to a balcony, framed by greenery and offering city views.

4.93 out of 5 average rating, 187 reviews

Hidden gem in Humber bay shores Toronto w/ parking

4.84 out of 5 average rating, 300 reviews

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍