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, 109 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

WalkabilityPetsHot tub

4.96 out of 5 average rating, 106 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!

Outdoor spacesWalkabilityAccuracy

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

Outdoor spacesWalkabilityParks

4.99 out of 5 average rating, 146 reviews

4.94 out of 5 average rating, 208 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

WalkabilityPetsFamily

4.98 out of 5 average rating, 367 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.

WalkabilityPetsAir conditioning

4.94 out of 5 average rating, 123 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.

WalkabilityPetsComfort

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, 142 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 spacesFamily

4.91 out of 5 average rating, 304 reviews

Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

Outdoor spacesPetsCondition

4.79 out of 5 average rating, 249 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 spacesWalkabilityBathroom

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 !

WalkabilityPetsHot tub

Superhost

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!

Outdoor spacesWalkabilityTV

4.88 out of 5 average rating, 152 reviews

4.92 out of 5 average rating, 264 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.

WalkabilityAmenitiesKitchen

Popular amenities for Pickering pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.91 out of 5 average rating, 107 reviews

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 spacesWalkabilityQuiet

4.93 out of 5 average rating, 101 reviews

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

PetsOutdoor spacesQuiet

4.97 out of 5 average rating, 117 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

PetsOutdoor spacesLocation

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 spacesQuiet

4.95 out of 5 average rating, 115 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

4.9 out of 5 average rating, 51 reviews

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

AccuracyIndoor spacesKitchen

5.0 out of 5 average rating, 19 reviews

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

DecorConditionFamily

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

WalkabilityHospitalityLocation

Pet-friendly home rentals with a pool

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.

New Custom-Built | Marble Pool + BBQ | Toronto

PetsOutdoor spacesAccess

4.91 out of 5 average rating, 148 reviews

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 spacesPetsValue

4.89 out of 5 average rating, 116 reviews

4.98 out of 5 average rating, 567 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)

WalkabilityPetsDecor

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.

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

PetsWalkabilityHiking

4.89 out of 5 average rating, 114 reviews

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.

Canadiana Downtown Condo w/King Bed + Free Parking

WalkabilityPetsAccess

4.92 out of 5 average rating, 184 reviews

4.9 out of 5 average rating, 170 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

PetsWalkabilityKitchen

4.82 out of 5 average rating, 123 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 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.

Charming Condo w Parking, CN Tower View & Pool

PetsWalkabilitySleep quality

4.94 out of 5 average rating, 150 reviews

Private, pet-friendly home rentals

5.0 out of 5 average rating, 70 reviews

Guest suite in Whitby

PetsNearbyGetting around

Superhost

A compact kitchen area features modern appliances, including a stainless steel stove and a microwave. A wooden table with two black stools provides a functional dining space. Light-colored walls and bright ceiling lights create a welcoming ambiance.

Guest suite in Pickering

GTA Suite | Lakeridge Ski Resort | Pickering GO

PetsValueDecor

4.83 out of 5 average rating, 48 reviews

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, 28 reviews

Cozy 4BR Near 401, 407 & Toronto

Outdoor spacesPetsKitchen

4.95 out of 5 average rating, 19 reviews

Luxury4BR | Steps to Lake Ontario| 2 Car Parking

WalkabilityFamilyCleanliness

4.93 out of 5 average rating, 75 reviews

A charming exterior of a spacious home is showcased, featuring a blend of stone and wood accents. Neatly trimmed hedges line a stone pathway that leads to the entrance. The well-maintained landscaping is complemented by a driveway and a garage.

Home in Scarborough

Private Pool Lakeview House

PetsOutdoor spacesBeach

4.84 out of 5 average rating, 62 reviews

3 bedroom bungalow in South Ajax

Outdoor spacesWalkabilityBathroom

4.98 out of 5 average rating, 98 reviews

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

Outdoor spacesPetsIndoor spaces