Pet-friendly holiday rentals in Caledon

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

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

4.99 out of 5 average rating, 405 reviews

A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.

Cabin in Arthur

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side! An hour from Toronto.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom 2nd BR bunk beds w/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly

Tiny home in The Junction

A stone pathway leads to the exterior of a small wooden cabin, surrounded by lush greenery. Hanging flower baskets adorn the walls, and a tranquil water feature can be seen nearby. The natural scenery creates a peaceful atmosphere, inviting exploration.

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, 168 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.

4.97 out of 5 average rating, 113 reviews

Home in Alton

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat

Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

4.87 out of 5 average rating, 179 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.

4.9 out of 5 average rating, 480 reviews

An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.

Cabin in Erin

Erin Cabin Getaway and Bunkie

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

4.93 out of 5 average rating, 280 reviews

A modern living area features a black sectional sofa adorned with decorative pillows. A light-colored throw is draped casually over the arm. A white desk with a chair sits nearby, along with a floral arrangement and a potted plant on the desk. A vibrant artwork depicting trees in fall colors is showcased above the sofa.

Home in Malton

5 Km to Toronto Pearson Airport , Sleeps 4-6

Tastefully decorated .cozy. luxurious 5 Km to Pearson Airport. 25 minutes to Union Station. downtown Toronto Lakeshore in Malton, Mississauga. Fully equipped kitchen large TV with Netflix etc. sleeps 4 -6, , One Car parking quiet neighborhood. . 3 Km to Malton GO Station, 10 min to International Centre. Toronto Congress Center. Woodbine Casino. Close to all Highways, Square One shopping mall. Well connected by public transport. Ride-sharing facilities in plenty.

4.97 out of 5 average rating, 144 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.

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, 184 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.

Guest suite in Orangeville

A serene winter scene captures a snowy landscape framed by tall evergreen trees. A clear blue sky contrasts with the bright white snow covering the ground and adjacent areas. The pathway leads towards a structure partly obscured by the snow-laden trees, suggesting a peaceful retreat.

4.96 out of 5 average rating, 171 reviews

Your Peaceful Santuary in Nature

Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.

Popular amenities for Caledon pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.9 out of 5 average rating, 475 reviews

A kitchenette area features modern cabinetry and countertop space, illuminated by recessed lighting. Decorative touches, including wall art and greenery, create a welcoming atmosphere. Appliances include a full fridge and microwave, with options for cooking, providing convenience for guests.

Home in Vaughan

Private Lower 1 BR + Sofabed Self Checkin with PKG

4.97 out of 5 average rating, 110 reviews

The exterior of the urban home is presented, featuring a dark blue façade and a sloped roof. A small, neatly landscaped front yard is enclosed by a black picket fence. Large windows allow for natural light, with a Canadian flag displayed proudly outside.

Home in Leslieville

Cozy Leslieville 2-Bedroom Home

4.94 out of 5 average rating, 108 reviews

A well-appointed bedroom features a spacious bed with a blue upholstered headboard. Decorative mirrors adorn the wall above the bed, and soft lighting from a lamp beside a small nightstand contributes to the room's brightness. A large window offers natural light and a view of the outdoors.

Home in Inch Park

Hamilton 2BR Gem Near Juravinski & Mohawk

4.96 out of 5 average rating, 312 reviews

A comfortable living room features a large sectional sofa and an armchair, complemented by a rustic coffee table. A brick fireplace serves as a cozy focal point, while a mounted television hangs above. Soft lighting enhances the inviting ambiance of the space.

Home in Port Dalhousie

Nautica Beach House on Lake Ontario

4.96 out of 5 average rating, 134 reviews

A spacious deck is showcased at night, featuring warm lighting that highlights its structure. An in-ground seating area with surrounding lights creates an inviting atmosphere. The surrounding landscape is visible in the background, providing a serene backdrop.

Home in Kitchener

RivertrailRetreat | Unique Deck + Skiing + Theatre

4.94 out of 5 average rating, 148 reviews

An open concept game room features a polished pool table at the center, with a bar area equipped with stools to one side. Large windows allow natural light to fill the space, while a mounted TV and comfortable sectional couch create an inviting entertainment area.

Home in Badjeros

JJ’s small town country retreat

4.94 out of 5 average rating, 159 reviews

The spacious living area features a light-colored sectional sofa arranged around a circular coffee table. A large Smart TV is mounted on the wall, while abstract artwork adorns the walls. Natural light enters through double doors leading to the patio, complemented by a decorative plant.

Home in Markham

2BR+2Bath! 2queen beds! Luxury Private Quiet Clean

4.89 out of 5 average rating, 123 reviews

A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.

Home in West Oakville

Large Luxury Villa with Swim Spa! Near downtown!

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 165 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

4BR-Year-Round Heated Pool & Hot Tub Family Oasis

4.97 out of 5 average rating, 102 reviews

A dining table with a circular glass top and four black chairs is positioned near large windows, offering expansive views of the Toronto skyline. A small potted plant adds a touch of greenery, while natural light fills the space, enhancing the modern interior.

Apartment in Fort York

The Farmer's Cottage

4.9 out of 5 average rating, 250 reviews

Cottage in Alcona

Utopia villa and spa

Condo in Humber Bay Shores

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

4.81 out of 5 average rating, 113 reviews

Humber Bay Family Friendly condo w Terrace&Parking

4.91 out of 5 average rating, 129 reviews

The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.

Condo in Kitchener

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

4.85 out of 5 average rating, 152 reviews

A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.

Home in Waterloo

Entire Guest Unit+Free Parking by Glenbridge Plaza

4.98 out of 5 average rating, 102 reviews

A desk with an ergonomic chair is positioned near floor-to-ceiling windows, offering a stunning view of Lake Ontario at sunset. The scene features a vibrant sky with hues of orange and purple, along with glimpses of the surrounding greenery and cityscape.

Condo in Fort York

Beautiful Lake View Studio Condo + 1 free Parking

Townhouse in West Queen West

A well-lit living area features two light-colored sofas arranged around a dark coffee table. A television is positioned on a white entertainment unit, with a stylish chandelier above. Large windows with sheer turquoise curtains allow natural light to enhance the hardwood flooring.

4.75 out of 5 average rating, 177 reviews

King West Triplex Main FLR PVT APT 1 BDRM Parking

Private, pet-friendly home rentals

4.97 out of 5 average rating, 60 reviews

Townhouse in Georgetown

Central Location Beautiful Full Townhome

4.89 out of 5 average rating, 37 reviews

A cozy living area features a striped sofa and two matching chairs, complemented by a wooden coffee table adorned with greenery. Soft lamps provide warm lighting, while dark curtains frame a window. A floral artwork adds a touch of color to the scene.

Condo in Brampton

Super Luxury Condominium in Brampton

4.88 out of 5 average rating, 25 reviews

A spacious living area features a comfortable dark sofa accompanied by a cozy throw blanket. A subtle area rug lies underneath, complementing the wooden flooring. A round dining table with four chairs is visible in the background, alongside a well-equipped kitchen and a closed door leading to another room.

Home in Brampton

Stylish Central Unit /1-Bed-Suite/Wi-Fi/Parking

4.86 out of 5 average rating, 70 reviews

A modern kitchen area features wooden cabinetry with textured tiles behind the stove. Stainless steel appliances are present, including a refrigerator and microwave. A large island with seating for four sits beside a dining table, while natural light streams in from nearby floor-to-ceiling windows.

Condo in Brampton

Modern & Luxury 1+Den Condo w/Parking

5 out of 5 average rating, 42 reviews

A modern kitchen area is visible, featuring white cabinetry and stainless steel appliances. A rustic barn door opens to the bedroom. The dining space includes a dark wood table surrounded by four chairs, complemented by a cozy sofa adorned with colorful cushions.

Guesthouse in Brampton

Private & Detached Downtown Brampton Garden Suite

4.89 out of 5 average rating, 27 reviews

A cozy studio space features a spacious bed with a white comforter and blue accent pillows. The kitchenette is visible in the background, equipped with white cabinets and modern appliances. A tray with two glasses and a bottle of wine rests on the bed, enhancing the welcoming vibe.

Home in Caledon

Live Lavishly: Modern Studio, 5G, Parking

4.96 out of 5 average rating, 28 reviews

A serene scene at dusk captures three animals, including a cow and two horses, walking along a path in a pasture. Sunlight filters through trees in the background, creating a warm glow over the landscape.

Farm stay in Orangeville

3 separate sleeping rooms on 23-acre horse farm