Pet-friendly vacation rentals in Caledon

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, 167 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.

4.91 out of 5 average rating, 151 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.

4.85 out of 5 average rating, 237 reviews

A private hot tub is nestled among trees, surrounded by softly glowing string lights. The inviting spa features a gray cover and beige trim, offering a serene retreat in nature.

Cabin in Hamilton

Hidden Cabin with hot tub

Immerse yourself in the woods. Experience the calmness and privacy of an off grid cabin in the woods, surrounded by nature and with a view of majestic horses. This cabin is perfect for a romantic getaway, or an escape with friends and family The large sliding glass door gives you the perfect view of a stunning morning sunrise with beautiful views of horses just steps away The Cabin consists of a main bedroom and also a full bathroom and kitchen to make your stay that much more comfortable

4.86 out of 5 average rating, 148 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!

4.98 out of 5 average rating, 107 reviews

Natural wood paneling surrounds a cozy seating area featuring a rectangular table and two chairs. A small nook is integrated into the design, providing space for storage. A dog rests on the floor, and a door opens to the outside, enhancing the connection to nature.

Cabin in Georgina

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Welcome to your next weekend retreat, or work from home during the week in a private nature focused environment with amazing wellness amenities. From the cedar Sauna and hot tub, game corner and indoor gas fireplace- we have your relaxation and entertainment covered. Host your dream dinner party with our gas range stove, pellet smoker and BBQ to choose from. You'll be sounded by cedar forest on all sides on our private road, just 1hr N-E of downtown TO. Ideal for groups of 2-3 couples

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, 454 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!

4.95 out of 5 average rating, 131 reviews

A relaxing outdoor space features a circular fire pit surrounded by four red Adirondack chairs. A stack of firewood sits nearby. Behind the seating area, a glimmering glass geodesic dome is surrounded by lush greenery and open sky.

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 $100/NIGHT ( 2 bunk beds)

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.

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.

4.98 out of 5 average rating, 294 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.

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, 168 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 pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.9 out of 5 average rating, 450 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

4.91 out of 5 average rating, 135 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

4.77 out of 5 average rating, 35 reviews

A covered hot tub area features wooden paneling and a vaulted ceiling with skylights, allowing natural light to fill the space. The hot tub, surrounded by stone tiles, creates a tranquil environment for relaxation, providing views of the greenery outside through large windows.

Home in Caledon Village

Charming and Peaceful Retreat with Hot Tub

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

4.85 out of 5 average rating, 26 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

4.85 out of 5 average rating, 151 reviews

An outdoor patio area is designed with comfortable seating arrangements, including a sectional sofa and ottomans. A pergola provides partial shade over the space, while greenery from nearby trees enhances the natural atmosphere. The wooden deck offers ample room for relaxation.

Home in Oak Ridges

Luxurious Spacious Dream Home with Parking!

4.95 out of 5 average rating, 148 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

4.96 out of 5 average rating, 145 reviews

A spacious living area features hardwood flooring and a ceiling fan. An entertainment unit with a television is centered against a white wall, coupled with a decorative fireplace. A comfortable gray sofa is positioned to the left, with a small dining table adorned with sunflowers on the right.

Home in Hamilton

Harbour front CHA CHA CHA - Lake view house

Pet-friendly home rentals with a pool

4.88 out of 5 average rating, 142 reviews

A panoramic balcony view reveals the iconic CN Tower alongside city skyline reflections on a modern glass building. Red outdoor seating provides a contemporary touch, surrounded by a spacious tile floor that invites relaxation amidst the urban landscape.

Condo in Harbourfront

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

4.86 out of 5 average rating, 190 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

4.99 out of 5 average rating, 159 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

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

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

4.9 out of 5 average rating, 105 reviews

A spacious living area is highlighted by a light-colored sectional couch, complemented by decorative cushions. A coffee table with a sailboat decor piece sits in the center. The open layout connects to a modern kitchen, featuring sleek appliances and bright lighting.

Home in Hamilton Beach

The Nautical Nook | Luxury Beach House

Condo in Entertainment District

A modern living area features a grey sectional sofa paired with a wooden coffee table. Natural light streams through large windows, revealing a view of the city. A 55-inch Smart TV is positioned on a dark wood console, complemented by decorative elements on the table.

4.93 out of 5 average rating, 120 reviews

Charming Condo w Parking, CN Tower View & Pool

Private, pet-friendly home rentals

4.99 out of 5 average rating, 71 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by comfortable seating in various patterns and colors. A wooden coffee table sits at the center, and a piece of artwork depicting a winter scene hangs above the mantel.

Home in Erin

Stonewell Farm Guest House

4.86 out of 5 average rating, 63 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, 44 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

5 out of 5 average rating, 34 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

Newly Constructed Downtown Brampton Garden Suite

Tiny home in Horning's Mills

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

4.91 out of 5 average rating, 180 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

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

3 separate sleeping rooms on 23-acre horse farm

4.96 out of 5 average rating, 47 reviews

A charming wooden structure is set against a backdrop of lush greenery. A bright red door serves as a focal point, complemented by a large deck with outdoor seating. Flowering plants and trees enhance the serene environment, creating a welcoming arrival space.

Apartment in Mono

Guest Suite in Hockley Valley