Pet-friendly vacation rentals in Pickering

A spacious back deck features a hot tub and seating area, surrounded by greenery. Large glass doors provide a view into the living room, while a cooking area and dining table are positioned outdoors. A metal container holds beverages, inviting relaxation.

4.93 out of 5 average rating, 105 reviews

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Bring your family or team together in this luxurious home! Beautifully refurnished in 2022, including a new hot tub and new hotel-quality mattresses & linens, this 4000 sq. ft house is ideally suited for large families or athletic teams. Featuring a remodeled kitchen w/ gas stove, 7 new beds (3 king), gym, office, smart TVs, 4 parking spaces & fast Wi-Fi. Only 5 minutes from the 401 & Ajax Go Train station, accessing the city is a breeze. Tennis + playground 50 meters away. *3 extra beds avail

PetsOutdoor spacesHospitality

4.83 out of 5 average rating, 222 reviews

The exterior of the villa is captured, showcasing a spacious driveway lined with several parked vehicles. A well-maintained garden features vibrant flower beds and neatly trimmed shrubs. The building's elegant stone façade is complemented by large front windows, with trees visible in the background.

Home in Kawartha Lakes

Luxurious Waterfront Vacation Villa Kolenchery.

Villa Kolenchery is one of the luxurious waterfront homes in Ontario, Canada.This facility provides a true paradise experience on the waterfront of Lake Scugog.This rental is suitable for families or friends that are looking for a place to gather, relax and enjoy activities like kayaking and fishing.Loud outdoor parties and music is prohibited as it is a quiet neighbourhood. Guests must respect the neighbours and no trespassing to neighbours property. Outdoor cameras are in place for monitoring.

Outdoor spacesPetsHot tub

4.92 out of 5 average rating, 87 reviews

A bright bedroom features a spacious bed with dark bedding, accented by light throw pillows. Nightstands with lamps are situated on either side. Large windows allow natural light, with curtains softly framing the view of the neighborhood outside.

Guest suite in Pickering

40min DT Toronto | PickeringGO|Lakeridge SkiResort

Welcome to our modern Pickering suite perfect for families, professionals, or leisure travelers. This newly built 3-bedroom, 2.5-bathroom suite offers memory foam beds, high-speed Wi-Fi, a Smart TV, an ensuite master bath, and dedicated workstations. Enjoy a chef-inspired kitchen, a cozy patio, and free street parking. Located less than 40 mins from downtown Toronto, our home offers easy access to numerous attractions, including golf courses, ski resorts, beaches, the zoo, a casino, and spas.

AmenitiesKitchenGetting around

4.94 out of 5 average rating, 203 reviews

A comfortable sofa in a neutral brown tone is positioned in the living room, complemented by a decorative blanket. In the background, a modern kitchen with bar stools and a light-colored counter is visible, along with a window allowing natural light into the space.

Apartment in Pickering

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

Legal lower-level basement apartment with kitchen and living room. Sleeps up to 6 guests with 2 queen beds and 1 sofa bed. Close to Hwy 401, restaurants, shopping, parks, Toronto Zoo, and GO Train. 🚗 *1 PARKING SPOT ONLY*. Additional vehicles may apply directly to the City of Pickering's Parking Consideration Program, subject to City approval. Any parking tickets or fines are the guest's responsibility. 👥 Extra Guests: $25/day 🌳 No smoking in/out of the property. 🔑 Private entrance

PetsWalkabilityWifi

4.98 out of 5 average rating, 359 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, this private loft includes your own 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.

WalkabilityPetsValue

4.94 out of 5 average rating, 122 reviews

A modern living area features a spacious gray sectional sofa and a minimalist coffee table. The walls are adorned with a gallery of framed artwork. A large window brings in natural light, while greenery adds a fresh touch to the room's bright yellow accent wall.

Townhouse in Whitby

EXQUISITELY DECORATED, 4 Bdrm Townhome W/ Parking!

Welcome to your home away from home!!! A Clean, Cozy and Exceptionally Decorated Luxury Home located just outside of Downtown Whitby and minutes to Hwy 401 & 407. This Trendy Townhome boasts tons of eye catching decor and is filled with every amenity your heart could desire. Equipped with 2 King beds, 2 Queen Beds and 2 full couches this Modern Townhome is perfect for a medium to large sized family or a handful of friends or associates looking for the perfect short or long term stay.

WalkabilityPetsCheck-in

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.

4.86 out of 5 average rating, 140 reviews

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

Contemporary 3 bed, 2 bath home w/ a European-feel. Centrally located on a low traffic court. Spacious, clean & bright! Featuring a large walk-out family room, high ceilings and wood-burning fireplace. Renovated w/ wood floors throughout. Large sunny west-facing backyard + 6 car-park on the driveway. Enjoy many unique amenities like our chromo-therapy steam room & outdoor Brazilian hammock. Walking distance to strip plaza, restaurants & parks. A comfortable home away from home!

WalkabilityOutdoor spacesAmenities

4.78 out of 5 average rating, 245 reviews

A serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.

Guest suite in Pickering

Muskoka on the City

Located in Rouge National Urban Park, steps from a beautiful lake and beach(Note:beach was temporarily closed by government now).Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Outdoor spacesWalkabilityView

5.0 out of 5 average rating, 21 reviews

Large house 3 bed 2 bath 2 parkings

Enjoy in the comfort of this stylish 3 bedrooms, 2 bathrooms huge house with outstanding facilities in the peaceful family-friendly neighbourhood of Pickering, close to GO station. Enjoy free access to high speed Wi-Fi, TV, fully functional kitchen, laundry, and work desks in two of the rooms. We trust that you will have an amazing time! Conveniently located close to Shopping, Dining, Pickering Casino, Hwy 401, and a 30-mins drive to downtown Toronto.

Outdoor spacesFamilyCheckout

4.99 out of 5 average rating, 187 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

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

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Outdoor spacesWalkabilityIndoor spaces

4.89 out of 5 average rating, 147 reviews

A spacious living area features a large sectional sofa facing a modern fireplace. Light wood flooring complements the warm color palette. An open floor plan is highlighted, with a view of the kitchen in the background, which includes sleek cabinetry and a large island.

Home in Oshawa

Modern 4BR Home in North Oshawa

Welcome to your modern 4BR, 3.5BA retreat in North Oshawa near Harmony & Collins. Perfect for families or professionals, this spacious home offers comfort and style with a bright open layout. Just 15 mins to malls, groceries & fine dining, with quick access to Hwy 401/407. Explore Lakeview Park, Parkwood Estate & Tribute Communities Centre nearby. Exterior security cameras ensure peace of mind. Early check-in/late check-out available!

WalkabilityPetsFamily

4.93 out of 5 average rating, 262 reviews

A cozy living area is presented with a grey sofa adorned with yellow cushions. A large TV is mounted on the wall, facing a white coffee table on a textured rug. A colorful abstract painting decorates one wall, complemented by a small indoor plant.

Apartment in Pickering

Lower Unit - Central location

Enjoy the charming touches of this cozy basement suite with a clean modern feel. Beautifully decorated featuring a spacious open concept living room/kitchen combo area with spacious island and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is bright and full of warmth. Conveniently located: 5 min walk to Pickering Town Center, 10 min walk to the Pickering GO and 2 min drive to 401.

WalkabilityValueAir conditioning

Popular amenities for Pickering pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 109 reviews

A modern kitchen with sleek cabinetry features a spacious island with seating for four. Large windows provide natural light and a view of the outdoors, while elegant pendant lights hang above. The adjacent living area showcases a comfortable sofa and a coffee table on a light-colored rug.

Home in Parkdale

Luxury home with 4 king suites near High Park

Outdoor spacesWalkabilityBackyard

4.82 out of 5 average rating, 135 reviews

An outdoor dining area features a long table set with plates and glasses, complemented by decorative elements like flowers. Soft string lights illuminate the space above, creating a warm ambiance. Nearby, a spa-like hot tub is situated under a wooden gazebo.

Home in Oshawa

Summer Getaway with HotTub, PoolTable • Sleeps 10+

PetsOutdoor spacesParking

4.97 out of 5 average rating, 113 reviews

A spacious dining area features a large wooden table surrounded by black chairs. A clock with a white face is mounted on the wall, and natural light fills the room through large windows. A view into the living area is visible in the background.

Home in Bond Head

3BR Spacious Home - KING BED

Outdoor spacesPetsHospitality

4.95 out of 5 average rating, 112 reviews

A charming two-story house is framed by flowering trees. The exterior features white siding and black window shutters, complemented by colorful potted plants at the entrance. A manicured lawn invites outdoor activities, while a small seating area is visible to the side.

Home in Scarborough

"Home Sweet Home"

Outdoor spacesPetsComfort

4.95 out of 5 average rating, 61 reviews

The Taunton House

Outdoor spacesSkiingLong stay

A well-lit living area features a mix of comfortable seating options, including two elegant chairs and a cozy sofa. A small coffee table sits at the center, complemented by a decorative area rug. Natural light filters through the windows, enhancing the soft color palette.

4.9 out of 5 average rating, 50 reviews

Spacious house for 14 |5BR| 6 Parkings |4Bath|

HospitalityIndoor spacesComfort

A well-lit stone pathway leads to a welcoming entrance adorned with elegant landscaping. Lush green shrubs frame the steps, illuminated by soft lights at the base of sturdy stone pillars, creating an inviting atmosphere for guests.

4.93 out of 5 average rating, 27 reviews

Mid-century Modern Castle | King Bed+Free Parking

WalkabilityPetsLocation

5.0 out of 5 average rating, 15 reviews

Luxury 2BR Suite| Stylish Stay w/ 2 Free Parking

LocationFamilyHospitality

Pet-friendly home rentals with a pool

Guesthouse in Mississauga

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.

4.89 out of 5 average rating, 114 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Outdoor spacesWalkabilityGrill

4.98 out of 5 average rating, 565 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

Outdoor spacesPetsKitchen

Guest suite in Scarborough

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

4.9 out of 5 average rating, 145 reviews

New Custom-Built | Marble Pool + BBQ | Toronto

PetsOutdoor spacesKitchen

Guest suite in Scarborough

A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.

4.88 out of 5 average rating, 112 reviews

1BR Bluffs | Pool + Yard | Pets Ok | EV Charger

WalkabilityPetsComfort

4.9 out of 5 average rating, 167 reviews

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

PetsWalkabilityFamily

Apartment in Downtown Toronto

A round marble dining table is featured in the center, surrounded by wooden chairs. Above hangs a stylish light fixture. A decorative hockey-themed wall art is displayed, reflecting local culture. The open kitchen area includes modern appliances and a neutral color scheme, enhancing the inviting space.

4.92 out of 5 average rating, 181 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

WalkabilityPetsCheck-in

4.82 out of 5 average rating, 120 reviews

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.

Condo in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

Outdoor spacesWalkabilityBathroom

Condo in Downtown Toronto

A rooftop pool reflects the blue sky while providing views of the CN Tower and surrounding modern buildings. Lounge chairs are positioned beside the pool, creating a relaxed atmosphere. The clear water invites enjoyment against the urban backdrop.

4.94 out of 5 average rating, 176 reviews

Rooftop Pool Condo with CN Tower View

Outdoor spacesWalkabilityAccuracy

Private, pet-friendly home rentals

The exterior of the home features a brick façade with a prominent arched window above the entrance. A paved driveway leads to a double garage with brown doors. Well-maintained shrubs and trees frame the entrance, contributing to a tidy appearance. A light cloud cover enhances the neutral tones.

4.96 out of 5 average rating, 27 reviews

Cozy 4BR Near 401, 407 & Toronto

PetsOutdoor spacesGrill

A modern living area features a cozy sofa and two stylish chairs arranged around a circular coffee table. A colorful area rug enhances the space, while large windows allow natural light to fill the room. Clear views of the outdoors can be seen through the glass doors.

4.93 out of 5 average rating, 28 reviews

Charming Family Townhouse

WalkabilityKitchenNearby

4.69 out of 5 average rating, 13 reviews

Home in Whitby

Ravine Oasis | Hot Tub, Sauna, Gym & Golf

LayoutValueSleep quality

5.0 out of 5 average rating, 4 reviews

Home in Unionville

Markham 5BR Entire Home| Kids Family | Near PAN AM

WalkabilityNearbyComfort

4.91 out of 5 average rating, 74 reviews

A well-maintained exterior of a two-story home is showcased, featuring a spacious driveway laid with patterned concrete. Lush greenery surrounds the property, and a deck is visible on the second floor, offering a view of the front yard and nearby trees.

Home in Scarborough

Spacious RougeView Home|2 Kitchens & 8-car Parking

Outdoor spacesWalkabilityCheck-in

4.98 out of 5 average rating, 64 reviews

A sleek kitchen area features a polished black marble countertop with unique veining. The backdrop is an elegant wooden wall with vertical slats, complemented by warm ambient lighting. The smooth marble flooring adds a touch of sophistication to the space.

Home in Vaughan

Luxury & Modern Home in Thornhill, Parking, Yard

WalkabilityOutdoor spacesIndoor spaces

4.93 out of 5 average rating, 15 reviews

Old English Charm: Spacious Home for Large Groups!

Outdoor spacesComfortIndoor spaces

An open-concept dining area is visible, featuring a wooden dining table surrounded by black chairs. A large clock adorns the wall above the table. Natural light filters through the window, illuminating the space. A staircase with dark wooden steps leads to the upper floor.