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Pet-friendly vacation rentals in Caledon

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Quick stats about vacation rentals that are pet-friendly in Caledon

  • Total vacation rentals

    Explore 240 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at €18 per night before taxes and fees

  • Verified guest reviews

    Over 7,150 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Caledon vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Caledon rentals

  • 4.7 Average rating

    Caledon stays receive an average rating of 4.7 out of 5 from guests

Top-rated pet-friendly home rentals in Caledon

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Guesthouse in Orangeville

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.

WalkabilityOutdoor spacesBathroom

4.96 out of 5 average rating, 404 reviews
Top guest favorite
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.
Apartment in Horning's Mills

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

PetsWalkabilityQuiet

4.96 out of 5 average rating, 347 reviews
Guest favorite
The exterior of the house features a combination of stone and wooden siding, with a pronounced roofline. A welcoming pathway leads to a spacious front deck, surrounded by manicured greenery and landscaping. Large windows and a colorful door enhance the inviting appearance.
Home in Alton

Cozy Fall Escape | HotTub + Fire Pit + River

Escape to the countryside this fall! Unwind in the hot tub under the stars, gather around the fire, and wake up beside the Credit River. Just under an hour from Toronto! Perfect for a relaxing getaway, girls weekend, or 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

PetsOutdoor spacesLaundry

4.96 out of 5 average rating, 135 reviews
Guest favorite
Home in Brampton

The Urban Nest

The Urban Nest: Spacious 3BR Oasis Close to YYZ⁠ 📍 PERFECTLY POSITIONED FOR TRAVEL & ENTERTAINMENT: Located in a vibrant, accessible area of Brampton, you are minutes away from excellent local dining, shopping, and major transit routes. If you are in town for big games or events, you will love how easily you can navigate to the main venues while returning to a quiet, peaceful neighborhood at night. Our summer calendar fills exceptionally fast. Secure your stay at The Urban Nest today!

WalkabilityPetsTV

4.9 out of 5 average rating, 108 reviews
Guest favorite
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!

PetsCheckoutComfort

4.86 out of 5 average rating, 285 reviews
Top guest favorite
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!.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom and queen bed in aw/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!

Outdoor spacesWalkabilityCheckout

4.99 out of 5 average rating, 434 reviews
Top guest favorite
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.
Guest suite in Orangeville

Garden Studio Orangeville

🌿 Country-Soul, Town-Heart Haven: Walk to Cafes, Mins to Premium Spas & PGA Golf. A 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.

WalkabilityOutdoor spacesNearby

5.0 out of 5 average rating, 203 reviews
Top guest favorite
Cabin in Guelph/Eramosa

Fern Hill Cabin

Escape to a hand-built Amish timber cabin on a peaceful 6-acre farm. Surrounded by willow trees, sheep, pigs, chickens, and a 150-year-old barn. It's your own country-spa retreat! Swim in the spring-fed pond, relax in the beautiful wood burning sauna, stargaze at night, and enjoy a compostable toilet with an unforgettable view! Restored century-old windows let in soft light and rustic charm. Ideal for anyone seeking quiet, nature, and a breath of fresh air.

PetsOutdoor spacesHospitality

4.99 out of 5 average rating, 114 reviews
Top guest favorite
A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.
Cottage in St. Jacobs

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

WalkabilityOutdoor spacesGetting around

4.99 out of 5 average rating, 210 reviews
Superhost
The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.
Villa in Burlington

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

PetsOutdoor spacesAccess

4.92 out of 5 average rating, 188 reviews
Guest favorite
A charming yellow house features a wide front porch with wooden seating and a grill. Lush greenery surrounds the porch, enhancing the outdoor space. The entrance is framed by a pair of glass doors flanked by symmetrical windows, inviting guests into the home.
Home in Orangeville

Central OVille,3 bed Victorian, walk to Lake, pets

This 3 bedroom (4 beds), 1,500 sqft unit with new Gas Fireplace and central A/C sleeps 6 adults comfortably. Bedroom 1 has a queen-sized bed, another a double bed while Bedroom 3 contains two separate single beds. There is large and beautiful private deck and fenced back yard that contains a full-sized BBQ The unit contains: Washer and dryer (within the unit), hard-wood floors, and free high-speed unlimited internet and HD Cable.

Outdoor spacesPetsAmenities

4.93 out of 5 average rating, 121 reviews
Superhost
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 & Bunkie. Your fall colour experience!

Escape to this unique and tranquil private retreat in Erin. Located just 350m from Calerin Golf Course and only 5 minutes from downtown Erin. Enjoy a private hot tub, BBQ, patio dining area, fire pit, pool table, games and acres of groomed trails. The cozy cabin features a queen bed, with a separate heated bunkie offering a second double bed. An optional pull-out bed is also available.

WalkabilityPetsBathroom

4.9 out of 5 average rating, 554 reviews

Popular amenities for Caledon pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favorite
A modern living area features light-toned walls and a plush area rug. A cozy seating arrangement consists of a sectional sofa and armchair, complemented by decorative cushions. A contemporary fireplace is situated below a stylish built-in shelving unit, showcasing an array of carefully curated decor.
Home in Mississauga

Luxury Modern 3Br Home In The Heart Of Mississauga

Outdoor spacesWalkabilityLocation

4.93 out of 5 average rating, 101 reviews
Top guest favorite
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

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

Outdoor spacesWalkabilityAccess

4.99 out of 5 average rating, 187 reviews
Top guest favorite
An expansive wooden deck features built-in seating and a sunken fire pit. The space is complemented by a BBQ station with a retractable cover, surrounded by lush greenery. A series of red outdoor chairs invite relaxation while the sky showcases a mix of clouds and sunlight.
Home in Kitchener

LUX 4BR• Theatre Room • Chef Kitchen • Unique Deck

Outdoor spacesWalkabilityCheckout

4.96 out of 5 average rating, 161 reviews
Guest favorite
A light-filled living area features a plush, beige sofa and armchairs arranged around a coffee table. A mirrored wall decoration reflects light, while a decorative chandelier hangs above. The space leads to a staircase and an entrance door with a decorative mirror nearby.
Home in Waterdown

Ninos Place

WalkabilityOutdoor spacesIndoor spaces

4.92 out of 5 average rating, 112 reviews
Guest favorite
A modern kitchen features sleek cabinetry and a large central island with seating for four. Pendant lights hang above the island, illuminating the space. Large sliding glass doors provide access to outdoor areas, enhancing natural light within the open layout.
Home in Hamilton

Luxurious 5BR Beach House with Firepit

Outdoor spacesWalkabilityGrill

4.9 out of 5 average rating, 189 reviews
Top guest favorite
A brightly lit living area features a red sofa adorned with decorative pillows. A wooden coffee table sits on a light rug, while large windows allow natural light to flood in, offering views of the surrounding greenery.
Home in Grand Valley

House on the bank of river

Outdoor spacesWalkabilityAccuracy

4.78 out of 5 average rating, 101 reviews
Top guest favorite
A floral wall in varying shades of pink is displayed prominently, featuring the words 'The Rose House' in glowing neon. Below the sign, a row of clear glasses rests on a light-colored shelf, inviting guests to enjoy a toast.
Home in Niagara-on-the-Lake

The Rosé House NOTL - Glam room - Old Town

PetsWalkabilityDecor

4.98 out of 5 average rating, 361 reviews
Top guest favorite
Home in Guelph

The Hat Maker's house near University of Guelph

WalkabilityOutdoor spacesCheckout

4.99 out of 5 average rating, 159 reviews

Pet-friendly home rentals with a pool

Superhost
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Mississauga

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Outdoor spacesWalkabilityDecor

4.89 out of 5 average rating, 116 reviews
Top guest favorite
Guesthouse in Breslau

House on the Hill

WalkabilityPetsKitchen

4.97 out of 5 average rating, 228 reviews
Guest favorite
A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.
Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

WalkabilityPetsAccuracy

4.9 out of 5 average rating, 170 reviews
Guest favorite
Cottage in Innisfil

Utopia villa and spa

Outdoor spacesWalkabilityKitchen

4.91 out of 5 average rating, 293 reviews
Top guest favorite
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.
Guest suite in Orangeville

Your Peaceful Santuary in Nature

Outdoor spacesPetsCheckout

4.96 out of 5 average rating, 189 reviews
Superhost
A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.
Home in Milton

Spacious, Pet Friendly Basement Apartment

PetsOutdoor spacesComfort

4.76 out of 5 average rating, 119 reviews
Superhost
A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.
Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

Outdoor spacesWalkabilityHospitality

4.92 out of 5 average rating, 126 reviews
Top guest favorite
A swimming pool is featured in a serene outdoor space, surrounded by lush greenery and tall trees. The circular pool is complemented by a stone wall background. A shaded seating area with a table and chairs is nearby, promoting relaxation and enjoyment.
Home in Don Mills

Casa Meya - Toronto Poolhouse Villa

Outdoor spacesWalkabilityHeating

4.91 out of 5 average rating, 107 reviews

Private, pet-friendly home rentals

Guest favorite
The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.
Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

PetsOutdoor spacesHiking

4.96 out of 5 average rating, 332 reviews
Superhost
Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.
Bungalow in Hamilton

Horse Ranch with Hot tub

WalkabilityOutdoor spacesView

4.92 out of 5 average rating, 230 reviews
Top guest favorite
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

Outdoor spacesPetsCondition

4.98 out of 5 average rating, 61 reviews
Top guest favorite
Guesthouse in Brampton

Guest House by Canterra Stays · Not a Basement

QuietDecorSleep quality

5.0 out of 5 average rating, 11 reviews
Guest favorite
A charming house is set against a serene evening sky, showcasing large front windows that allow for natural light. The exterior features a combination of gray siding and earthy tones, with a small porch and a well-maintained driveway leading to a single-car garage.
Home in Tottenham

Pond View Gardens

Outdoor spacesPetsAccess

4.88 out of 5 average rating, 57 reviews
Guest favorite
An outdoor dining area is set with a dark table surrounded by comfortable chairs. Elegant tableware and floral arrangements decorate the table, while soft lighting creates a warm ambiance against a backdrop of lush greenery.
Villa in Kettleby

Entire Villa with beautiful fenced backyard

PetsOutdoor spacesNearby

4.98 out of 5 average rating, 98 reviews
Guest favorite
An aerial view showcases the expansive countryside surrounding the farmhouse, featuring lush green lawns and winding rivers. The property is framed by landscaped gardens and meticulously arranged stone pathways, leading to an inviting entrance. The picturesque setting is perfect for appreciating nature's tranquility.
Home in Waterloo

Charming Farmhouse Stunning Views & Hot tub

Outdoor spacesPetsValue

4.93 out of 5 average rating, 70 reviews
Guest favorite
Home in Erin

Bright & Spacious 3 Bedroom Home

Sleep qualityParkingFamily

5.0 out of 5 average rating, 30 reviews

When is the best time to visit Caledon?

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Avg. price€83€92€84€79€94€112€96€105€91€83€84€91
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