Pet-friendly holiday rentals in Pickering

Guest suite in Scarborough Village

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, 104 reviews

Prestigious Bluffs Private Guest Suite

Beautiful, private, sun-filled guest suite with a large private yard and pool in a safe, upscale, tranquil, forested neighbourhood. Deer and other wildlife. Short walk to public transport (TTC, GO Trains), shopping, restaurants, parks and trails to the top of the Bluffs with breathtaking views of Lake Ontario and also down to the waterfront trail to nearby Bluffers Park Beach and Marina. Parking for 6 vehicles and boat trailer. Fast Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

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.

4.99 out of 5 average rating, 115 reviews

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.

4.88 out of 5 average rating, 205 reviews

A modern kitchen area is displayed, featuring white cabinetry and stainless steel appliances. A sleek, circular coffee table is positioned in front of a comfortable white sofa, with light hardwood flooring throughout. Natural light illuminates the space from a nearby window, enhancing the contemporary décor.

Home in Mississauga

Private 1-br Apartment: Your Secluded Getaway!

Welcome to our modern, fully-equipped unit that features a spacious backyard. Whether you are traveling for business or pleasure, our unit is the perfect base. The location provides convenient access to everything, just 10 minutes from downtown Toronto and the airport, 5 minutes from Lakeshore Blvd, Port Credit, and the GO stn, and steps away from public transportation. Additionally, you will find a plethora of local restaurants, shops, a scenic walking trail, and beautiful parks in the area.

4.97 out of 5 average rating, 120 reviews

Flat in Port Perry

Romantic & Cozy Countryside luxury loft with views

Romance in the Country. Getaway from the hustle with your sweetheart, to play, rest/work stay-cation. Newly built, full kitchen, bath/laundry/EV charger. Great trails, theatre, shopping in quaint downtown Port Perry, boating, golfing, equestrian farm, museums, & amazing 5 star restaurnts in Port Perry. Enjoy the pond on the property & lots of places to enjoy peace & quiet together! Ask about our Chef and Pontoon experiences. 1 hr from TO, 8 min to Port Perry. We have 2 rms queen loft/king.

4.95 out of 5 average rating, 146 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

Fully renovated, modern, Bright, luxurious, and spacious ( over 1800 sq/ft) 2-bedroom, 2-bathroom high ceiling above ground apartment, separate entrance, and Patio for your next cozy home away from home! 5-star rated and top 5% of homes in AirBnB! As central as it gets in the GTA. You'll be close to Pearson Airport, Highway 401/404/407, shopping malls, grocery stores, and an array of trendy restaurants, movie theaters, parks, and bicycle/ hiking trails all around Book With Confidence!

4.84 out of 5 average rating, 112 reviews

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.

Home in Pickering

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

Welcome! Our 3 bedroom, 2 bath home is centrally located on a low traffic court. Spacious, clean and bright! Featuring a large walk-out family room with high ceilings and a wood-burning fireplace. Completely renovated with wood floors throughout. Large sunny west-facing backyard and 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!

4.97 out of 5 average rating, 235 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 in 2021, this private loft includes a 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.

4.96 out of 5 average rating, 148 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

Spacious lower-level legal basement apartment featuring open-concept living room & kitchen. 2 queen-sized beds & 1 sofa bed. Located near the 401, grocery stores, restaurants, malls, casinos, parks, Toronto Zoo & 5-minute drive to the GO Train. 1 vehicle parking. Electric car charging $10/day Extra guests $25/day. Private side entrance for self-check in with access code. ✅ Wi-Fi, iMac & Printer ✅ TV Box with Netflix/Amazon Prime ✅Variety of Board Games ✅ Full Kitchen w/condiments

Guest suite in Bedford Park

A living room features a gray sofa accented with decorative cushions, paired with two mid-century modern chairs. A large window allows natural light to illuminate the space. A mounted flat-screen TV and an electric fireplace are visible, enhancing the cozy atmosphere.

4.89 out of 5 average rating, 253 reviews

Midtown Luxury Yonge/Lawrence Close to Downtown

Located in the upscale Yonge & Lawrence Village in Midtown Toronto. Steps to Yonge St. bus, 5 min walk to the Subway. The heart of the city is within minutes. There are several restaurants, coffee shops, pubs & bars within a 1-5 min walk. Public tennis courts, parks. The suite is completely self-contained. We live on the main floor above, we are usually available help. There is a 75"Samsung TV, 2 Extra large washers and 2 Extra large Gas dryers for all of your laundry needs.

A modern living area features a stylish black sofa and a glass coffee table, complemented by a round dining table with four wooden chairs. Large windows allow ample natural light, enhancing the clean lines of the space. A decorative mirror adds depth to the room.

4.85 out of 5 average rating, 122 reviews

Trendy & Cozy 1BD Condo in the Heart of Toronto

Enjoy a trendy and cozy experience at this centrally located condo. This 1 bedroom, 1 bathroom unit is located in the heart of the city within walking distance to many of Toronto's most popular restaurants, bars and tourist destinations. Steps away from King street, The Well and walking distance from the CN Tower, Rogers Centre, Ripley' s Aquarium and much more. The unit is equipped with high speed Wi-Fi with unlimited internet. You can also enjoy the gym and studio room.

4.88 out of 5 average rating, 24 reviews

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

Welcome to our cozy studio, perfect for couples or professionals! The space includes a folding queen bed for flexibility, a dining table that doubles as a desk, and a portable couch. Enjoy shared laundry access, high-speed Wi-Fi, a smart TV, and free parking. Located less than 15 minutes from Pickering GO Station, our unit offers easy access to the GTA and is close to attractions like golf courses, ski resorts, beaches, the zoo, a casino, and spas.

4.91 out of 5 average rating, 127 reviews

The exterior of a modern home features a stone facade, highlighted by outdoor lighting. A decorative entrance is flanked by large planters filled with vibrant flowers. The driveway leads up to a garage with contrasting colors, enhancing the inviting atmosphere of the residence.

Guest suite in Oshawa

Spacious Guest Room close to 401

Welcome to our spacious and stylish 1 bedroom in the basement, perfectly suited for couples or individuals seeking a memorable stay. Nestled in a centrally located location, this hidden gem offers quick and easy access to all the amenities you could wish for. Centrally located, just 2 mins from the 401, gas stations, and McDonald's, and 5 mins from Costco. Durham College is a quick 15-min drive. License Number RHSTR2025001

Popular amenities for Pickering pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.81 out of 5 average rating, 26 reviews

A modern kitchen is featured, showcasing sleek stainless steel appliances including a refrigerator, microwave, and stove. White cabinets provide contrast against the light-colored backsplash, while a spacious countertop offers ample preparation space. The well-lit area enhances the kitchen's functionality and appeal.

Home in Wismer

Modern & Private 2BR Suite

4.82 out of 5 average rating, 170 reviews

A spacious living area showcases a large grey sectional sofa, accented by yellow throw pillows. A sleek coffee table sits in front, with a decorative plant and tray. In the background, a mirrored wall reflects natural light, and a dining area is visible, featuring black chairs and a table.

Home in Malton

3 BR 2 WR Entire home 5 Km Toronto Pearson Airport

4.9 out of 5 average rating, 449 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

4.9 out of 5 average rating, 209 reviews

An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.

Home in Oakwood Village

Family Home Near St Clair W and Public Transport

4.97 out of 5 average rating, 34 reviews

An open living area features a stylish fireplace, a yellow sectional sofa, and a modern TV unit. The kitchen includes sleek cabinetry and stainless steel appliances. Soft lighting and neutral tones create a bright and inviting design, complemented by a plush area rug underfoot.

Home in Richmond Hill

Newly Renovated Bright Suit with Free Parking

5 out of 5 average rating, 3 reviews

Home in Markham

Backs onto nature near IBM and Hospital

5 out of 5 average rating, 21 reviews

A spacious living area features two dark leather sofas facing a coffee table. A wall-mounted TV is positioned above an electric fireplace. Natural light enters through two large windows with soft shades, while a dining area with wooden chairs is visible in the background.

Home in Pickering

Just Like Home- Brand New 4 Bedroom Home

4.94 out of 5 average rating, 584 reviews

An outdoor seating area is showcased, featuring a comfortable couch adorned with patterned cushions. Flanking the couch, two red chairs face a wooden fence, while a decorative lantern and potted plants add touches of greenery, highlighting the inviting atmosphere of this private space.

Home in Cabbagetown

Comfy Oasis In Historic Downtown Neighborhood

Pet-friendly home rentals with a pool

A softly lit bedroom features a spacious bed with a tufted headboard, complemented by white linens and decorative pillows. A bedside table with a lamp sits on one side, while a flat-screen TV is mounted on the wall. Natural light filters through sheer white curtains.

4.82 out of 5 average rating, 111 reviews

Lux Spacious 3 Beds w CN Tower View (Free Parking)

4.98 out of 5 average rating, 556 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)

4.87 out of 5 average rating, 189 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.

Apartment in Mississauga

Beautiful Penthouse with Breathtaking View

4.99 out of 5 average rating, 158 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

4.86 out of 5 average rating, 236 reviews

A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.

Apartment in Mississauga

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

Townhouse in West Queen West

A well-lit living area features two light-colored sofas arranged around a dark coffee table. A television is positioned on a white entertainment unit, with a stylish chandelier above. Large windows with sheer turquoise curtains allow natural light to enhance the hardwood flooring.

4.75 out of 5 average rating, 175 reviews

King West Triplex Main FLR PVT APT 1 BDRM Parking

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

4.89 out of 5 average rating, 110 reviews

Spacious And Sun Filled, Modern

Private, pet-friendly home rentals

Guest suite in Richmond Hill

A well-lit bedroom features a spacious bed dressed in a striped white duvet. Geometric patterned pillows add visual interest. A mirror and framed artwork are displayed above a wooden dresser, which holds decorative items and a stylish lamp, enhancing the room's modern decor.

4.96 out of 5 average rating, 94 reviews

Tranquil Ambience with a Private Washroom

5 out of 5 average rating, 26 reviews

A modern kitchen area features sleek white cabinetry and stainless-steel appliances, including an oven, microwave, and dishwasher. A clean countertop space is complemented by a small plant, while a dining table is visible in the background, creating a spacious and functional layout.

Guest suite in Whitby

Sage Garden: Premium Apt 2B/1B, Kitchen, Parking!

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.

Guest house in Brampton

Newly Constructed Downtown Brampton Garden Suite

4.88 out of 5 average rating, 17 reviews

A living area is presented with a blue sofa and a light-colored coffee table. Two lamps provide soft lighting, and a dining table with four chairs is visible. The adjoining kitchen features dark cabinetry and modern appliances, creating a harmonious open space.

Apartment in Oakville

Comfy condo, can sleep 5, close to stores, park

4.81 out of 5 average rating, 16 reviews

An inviting dining area features a round table surrounded by four chairs. The space is brightly lit with recessed lighting and has a modern design, with a kitchen visible in the background, showcasing white cabinets and a refrigerator.

Guest suite in Ajax

Daisy Den: Modern Apt 2B/1B, Kitchen, Parking!

4.84 out of 5 average rating, 74 reviews

The living area is designed with modern furnishings, featuring a gray sofa paired with two bright red chairs. A round coffee table is set with decorative items, including a plant. A painting above the sofa adds a pop of color, while natural light filters through the large windows.

Flat in Mississauga

Modern 1 Bed Condo Mississauga

4.86 out of 5 average rating, 42 reviews

A spacious sleeping area features a large bed dressed in neutral linens. A cozy armchair is positioned by the window, which is covered with light-filtering shades. Two lamps stand beside the bed, and a decorative wall frame showcases earthy art. A soft area rug adds warmth to the floor.

Flat in Clarington

Private Guesthouse in Bowmanville