Pet-friendly holiday rentals in Caledon

4.79 out of 5 average rating, 369 reviews

A view from the backyard showcases a green and lush landscape, with trees framing the scene. In the background, a multi-story building is visible, along with sloped rooftops of nearby structures. The quiet neighborhood is highlighted by an abundance of greenery and open spaces.

Guest suite in Fergus

Mill View

Close to the Sportsplex, we have a spacious walk-out backyard & picnic table. A beautiful view; quiet neighborhood. Close to amenities and shopping, hiking and biking trails, Belwood Lake, Elora Gorge, Elora Mill and Quarry. Excellent for couples, solo adventurers, business travellers, and we're pet friendly! Free WiFi. A double (not queen) bed and private washroom with shower. Games room with pool table, tabletop hockey and darts. Fridge, freezer, toaster oven, kettle, microwave & cooktop.

4.81 out of 5 average rating, 101 reviews

A serene living area is depicted, featuring a spacious bed, a smart TV, and a dining table set for two. Natural light enters through the door, which leads to an outdoor space. Soft carpeting and neutral-colored walls create a calm environment.

Home in Brampton

Your Own Suite-Moderncharm Hideaways Near TorAirp

Charming Executive Suite with Large Backyard on Ravine Just minutes away from Toronto International Airport, a variety of amazing restaurants (including authentic Indian cuisine),grocery stores This suite is perfect choice for a weekend getaway, business trip, staycation, work-from-home alternative, or a cozy home base while exploring Toronto best The unbeatable location puts you 24 minutes from Downtown Toronto, 1.5 hours from Niagara Falls. And the breathtaking fall colors of North Country.

4.99 out of 5 average rating, 401 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, 164 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.

Guest house 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.

4.91 out of 5 average rating, 150 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, 237 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

4.86 out of 5 average rating, 143 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.

4.97 out of 5 average rating, 109 reviews

Home in Alton

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • 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

4.91 out of 5 average rating, 450 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!

4.96 out of 5 average rating, 134 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.

Guest house 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.

4.98 out of 5 average rating, 293 reviews

A rustic living area features exposed wooden beams and a stone fireplace, providing a cozy focal point. Comfortable seating options include an armchair and a sofa arranged around a wooden coffee table. Large windows allow natural light to illuminate the space.

Guest suite in Mono

Mono - Charming, Rustic 150 Year Carriage House

This rustic space is perfect for a weekend getaway, year round. Close to ski hills, nature trails and the quaint town of Orangeville the Carriage house will provide you the authentic feel of our iconic cabin in the woods with the sophistication and comforts of your personal retreat for the weekend. The interior design is eclectic, funky and perfectly contrasts the rustic charm of the 140 year old, hand cut wooden beams and the overall log cabin environment.

Popular amenities for Caledon pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 314 reviews

A modern dining area features a wooden table set for a meal, surrounded by light-colored chairs. A large window on the wall allows natural light to brighten the space, showcasing a view of greenery. The adjoining kitchen is visible in the background.

Home in Paris

The Walnut - Steps to Canoe Launch & Downtown

4.86 out of 5 average rating, 125 reviews

A bright living and dining area features a comfortable sofa adorned with decorative cushions. A dining table with chairs is positioned nearby, and a flat-screen television is mounted on the wall. Modern cabinetry is visible in the background, complemented by warm lighting.

Home in Brampton

Spacious 3-Bed Home near Airport. Parking Backyard

4.91 out of 5 average rating, 134 reviews

An open-plan kitchen and dining area is depicted, showcasing modern appliances and cabinetry. A black dining table with four chairs is placed near the entrance, with a small desk nearby. Warm lighting highlights the light-colored flooring and walls, creating a bright and inviting space.

Home in East Woodbridge

Bright Spacious 1BR Basement Suite - Private Entry

4.97 out of 5 average rating, 119 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, 133 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

4.84 out of 5 average rating, 113 reviews

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

Home in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

4.95 out of 5 average rating, 146 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

4.98 out of 5 average rating, 127 reviews

The exterior of a brick home is showcased, featuring a well-maintained front yard with trimmed shrubs and a large evergreen tree. The two-car garage has white doors with windows, and a paved driveway leads to the entrance. A clear blue sky enhances the welcoming appearance.

Home in Guelph

Spacious Guelph Retreat. Sleeps 9. Park 4 Cars.

Pet-friendly home rentals with a pool

Villa in Niagara-on-the-Lake

An aerial view captures the villa nestled among lush greenery, showcasing a saltwater pool surrounded by lounge chairs. The structured layout of the property is visible alongside the landscaped backyard, offering a serene outdoor space for relaxation.

4.85 out of 5 average rating, 151 reviews

Bright & Beautiful Villa with Pool

4.87 out of 5 average rating, 189 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.

Apartment in Mississauga

Beautiful Penthouse with Breathtaking View

4.99 out of 5 average rating, 158 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

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

4.9 out of 5 average rating, 240 reviews

A loft area features a wooden railing adorned with greenery, providing a cozy viewing spot. A circular wooden table is accompanied by two matching folding chairs, inviting relaxation. Warm lighting enhances the natural wood tones of the ceiling and walls, creating a welcoming ambiance.

Cottage in Alcona

Utopia villa and spa

4.95 out of 5 average rating, 117 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.

Apartment in Kitchener

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

4.85 out of 5 average rating, 130 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

Guest house 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.

4.95 out of 5 average rating, 374 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

4.8 out of 5 average rating, 265 reviews

Apartment in Fort York

Stylish 1+1 Corner Suite |Steps to Lake&Downtown

Private, pet-friendly home rentals

5 out of 5 average rating, 41 reviews

A hand-crafted cabin features a dark exterior with bright wooden accents, surrounded by tall trees. A welcoming porch includes a small table and chairs, extending towards a natural landscape covered in wood chips.

Cabin in Guelph-Eramosa

Fern Hill Cabin

4.87 out of 5 average rating, 61 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.

Apartment in Brampton

Modern & Luxury 1+Den Condo w/Parking

4.94 out of 5 average rating, 196 reviews

A doorway opens to a private deck featuring two wooden chairs with white cushions and a small table between them. The view showcases lush greenery and rolling farmland, under a clear sky.

Guest house in Lincoln

Little Blue Barn on the Bench

Guest suite in Mississauga

A cozy bedroom with a spacious bed dressed in white bedding and accented by neutral-colored pillows. Two bedside lamps illuminate the space, complemented by artwork featuring botanical prints on the wall. Natural light filters through a small window, enhancing the calm atmosphere.

4.94 out of 5 average rating, 169 reviews

Bright apartment/basement in Mississauga

5 out of 5 average rating, 20 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

2 bedrooms on 23-acre horse farm

4.81 out of 5 average rating, 16 reviews

A spacious living area is presented with a modern grey sofa, complemented by decorative pillows. A large flat-screen TV is mounted above a stylish electric fireplace. The kitchen and dining area are visible, featuring sleek appliances and a round dining table with chairs, all designed in an open-concept layout.

Flat in Caledon

High Ceiling | Opulent Touche | Comfort stay

4.88 out of 5 average rating, 153 reviews

A rustic cabin, partially visible through snow-covered trees, features a warm wooden exterior. Snow blankets the roof and surrounding ground, while sunlight filters through the branches, creating a serene winter atmosphere. A wrap-around deck is seen at the front of the cabin.

Cabin in Georgina

Romantic Cabin N the Woods just 80km from CN Tower