Pet-friendly holiday 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.

4.94 out of 5 average rating, 108 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

PetsWalkabilityHot tub

4.96 out of 5 average rating, 105 reviews

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

PetsWalkabilityBack garden

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|

Nestled in the serene neighborhood of Pickering, Ontario, this charmingly furnished home offers a tranquil retreat for up to 12 guests and an infant. 25-30 minute drive from downtown Toronto. Surrounded by the Rouge National Urban Park, explore scenic trails and enjoy nature walks. Nearby attractions are waterfront of Frenchman's Bay, Pickering Museum Village, and the Toronto Zoo. With easy access to both natural beauty and city excitement, this home is an ideal getaway for families and groups!

AmenitiesBathroomAccess

4.9 out of 5 average rating, 89 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.

ValueLocationSkiing

4.94 out of 5 average rating, 205 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.

Flat 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

PetsWalkabilitySolo travel

4.98 out of 5 average rating, 364 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.

WalkabilityOutdoor spacesAccuracy

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.

PetsWalkabilityQuiet

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.

4.87 out of 5 average rating, 141 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!

PetsWalkabilityPool

4.79 out of 5 average rating, 247 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 spacesWalkabilityLocation

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 spacesBathroomLocation

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 !

PetsOutdoor spacesCheck-in

4.89 out of 5 average rating, 150 reviews

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!

WalkabilityPetsCondition

Popular amenities for Pickering pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 114 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 spacesPetsTV

4.93 out of 5 average rating, 141 reviews

A spacious backyard features a fire pit surrounded by four adirondack chairs. The cottage showcases large windows and a deck with outdoor dining furniture and an umbrella. Two kayaks are stored nearby, adding to the lakefront atmosphere.

Home in Kawartha Lakes

Cozy Lakeside Cottage on Lake Scugog

PetsOutdoor spacesKitchen

4.97 out of 5 average rating, 115 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 spacesPetsAccuracy

4.94 out of 5 average rating, 63 reviews

The Taunton House

Outdoor spacesHospitalityLayout

4.95 out of 5 average rating, 19 reviews

Luxury4BR | Steps to Lake Ontario| Near GO Station

WalkabilityAmenitiesCleanliness

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

WalkabilitySleep qualityComfort

5.0 out of 5 average rating, 8 reviews

Soleil Nest - 5 beds, 2.5 baths, 2 park, Backyard

CleanlinessConditionLocation

4.84 out of 5 average rating, 62 reviews

3 bedroom bungalow in South Ajax

WalkabilityOutdoor spacesAccuracy

Pet-friendly home rentals with a pool

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.

4.89 out of 5 average rating, 114 reviews

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

PetsOutdoor spacesGetting around

4.98 out of 5 average rating, 566 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)

WalkabilityOutdoor spacesIndoor spaces

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

WalkabilityOutdoor spacesQuiet

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.

Guest house in Mississauga

4.89 out of 5 average rating, 116 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Outdoor spacesWalkabilityCheckout

4.92 out of 5 average rating, 182 reviews

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.

Flat in Downtown Toronto

Canadiana Downtown Condo w/King Bed + Free Parking

WalkabilityPetsTV

4.9 out of 5 average rating, 168 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.

Apartment in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

WalkabilityPetsLaundry

4.82 out of 5 average rating, 122 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.

Apartment in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

WalkabilityOutdoor spacesQuiet

Apartment 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, 178 reviews

Rooftop Pool Condo with CN Tower View

WalkabilityPetsBathroom

Private, pet-friendly home rentals

4.94 out of 5 average rating, 18 reviews

Old English Charm: Spacious Home for Large Groups!

Outdoor spacesCleanlinessKitchen

4.98 out of 5 average rating, 65 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 spacesParks

4.91 out of 5 average rating, 77 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

WalkabilityOutdoor spacesBack garden

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, 29 reviews

Mid-century Modern Castle | King Bed+Free Parking

WalkabilityPetsGetting around

Superhost

Home in Whitby

4.77 out of 5 average rating, 79 reviews

Stylish 4BR Townhouse (TV in every room, GameRoom)

PetsWalkabilityNearby

Superhost

A bright dining area features a round table surrounded by four white chairs. A large window with sheer curtains allows natural light to fill the space, revealing a view of greenery outside. A vase with pink flowers is placed at the center of the table.

Bungalow in Pickering

4.76 out of 5 average rating, 71 reviews

Entire spacious private Home steps to Beach

PetsOutdoor spacesLong stay

5.0 out of 5 average rating, 69 reviews

Guest suite in Whitby

PetsCleanlinessNearby