Pet-friendly holiday rentals in Oshawa

4.93 out of 5 average rating, 104 reviews

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.

Home in Ajax

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

WalkabilityOutdoor spacesKitchen

Shipping container in Clarington

An outdoor stone wall shower is positioned next to a wooden deck, leading to a private pond. The deck features a covered area with dining furniture. Lush greenery surrounds the space, and sunlight illuminates the scene under a clear blue sky.

4.98 out of 5 average rating, 117 reviews

Rustic Ridge

Rustic Ridge Tiny Cabin - Cozy Escape on Private Pond **Cabin will have to be winterized when temperature drops meaning no running water and outdoor shower, jugs of water will be supplied to rinse after sauna, bottled water in dispenser also provided.*** Welcome to Rustic Ridge Tiny Cabin, a unique shipping container retreat on the back of our property. Nestled by a private pond with a fountain, this serene cabin is the perfect escape for nature lovers and those looking to unwind in comfort.

Outdoor spacesPetsQuiet

4.98 out of 5 average rating, 562 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)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

PetsWalkabilityAir conditioning

4.94 out of 5 average rating, 146 reviews

The spacious studio features a queen-sized bed with a checkered comforter and decorative pillows. A large Samsung 55-inch Smart TV is positioned on the entertainment unit, offering various streaming options. A workstation is visible in the background, providing a comfortable space for productivity.

Flat in Bowmanville

The Cozy Cove Studio

Cozy and private 1-bed studio, ideal for short or extended stays, well-equipped for convenience and relaxation. ✔︎ Spacious private suite with full Bath ✔︎ 55-inch 4K TV with Netflix, Prime, Crave, Fibe TV, YouTube, etc ✔︎ Super Fast WiFi ✔︎ Self check-in ✔︎ Workstation ✔︎ 5 mins drive - 401, Downtown, Malls, Grocery, Pharmacy, Restaurants, Cineplex. ✔︎ Free Parking on driveway ✔︎ In Unit Washer & Dryer ✔︎ Kitchenette - Fridge, Microwave, Kettle, Toaster, Coffee maker, utensils & supplies.

WalkabilityPetsHeating

4.98 out of 5 average rating, 353 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.

Outdoor spacesWalkabilitySolo travel

4.88 out of 5 average rating, 196 reviews

A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.

Cottage in Bowmanville

“Lakeside Dreams”: All season HotTub w/lake views

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

PetsWalkabilityGrill

4.94 out of 5 average rating, 119 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.

WalkabilityPetsHiking

4.86 out of 5 average rating, 136 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.

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!

Outdoor spacesPetsCondition

4.89 out of 5 average rating, 262 reviews

A tranquil view of a lake reflects the colorful hues of the sunset, with a modern building nestled among trees on the opposite shore. The surrounding landscape features gentle slopes leading to the water, creating a peaceful natural setting.

Guest suite in Newcastle

Romantic Nature Retreat - Hydrotherapy Suite

A Romantic Retreat, located on 91 acres, beside a small, spring-fed lake, this is a private hydrotherapy suite with its own sitting area and firepit, providing a relaxing getaway close to the city. Gentle walking trails and abundant wildlife around the lake Swimming, dock, canoe & paddleboat Ideal for two people, 2SLGBTQ+ all welcome 6 min drive to Newcastle for dinner, shopping... Please read reviews & full ad before booking. Pets are welcome.

Outdoor spacesPetsParking

4.9 out of 5 average rating, 140 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!

Outdoor spacesWalkabilityComfort

4.93 out of 5 average rating, 257 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.

Flat 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.

WalkabilityAir conditioningCheckout

4.9 out of 5 average rating, 114 reviews

The modern townhome exterior features a clean brick facade and large windows providing ample natural light. A set of steps leads to the main entrance, framed by black railings on either side. A small potted plant sits at the base of the steps.

Townhouse in Pickering

The Cyberspace (No cleaning fees, Private Hot Tub)

Private hot tub! No cleaning fees! This stylish modern townhome is the perfect place to stay for you and your family. Two car garage, 4 parking spots, 4 bedrooms, 4 bathrooms, pool & ping pong table, arcade game, Occulus, BBQ, exercise equipment, hot tub, walk to: store, pizza, and Cannabis shop. Fibreoptic internet for working from home/streaming. Local and trusted ride services available at competitive rates. USA friendly!

WalkabilityPetsBathroom

Popular amenities for Oshawa pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 40 reviews

Home in Oshawa

Cozy Haven | Relax, Unwind & Feel at Home

Indoor spacesComfortHeating

5.0 out of 5 average rating, 7 reviews

Home in Courtice

Blossom Nest - 4 beds, 2.5 baths, 3 park

Sleep qualityHospitalityFamily

4.93 out of 5 average rating, 14 reviews

A detached house is shown, featuring a light brick facade and multiple large windows. The entrance is highlighted by a covered porch with stylish railings. Two garage doors are present, set against a smooth driveway bordered by green grass.

Home in Oshawa

EastCity 4BedRoom DetachedHouse

Outdoor spacesConditionCheckout

5.0 out of 5 average rating, 49 reviews

A living room space features a gray sofa with yellow accent pillows and a matching armchair. A neutral coffee table is positioned on a decorative blue area rug. Bright lighting enhances the features of the room, with a painting of a serene landscape adorning the wall.

Home in Courtice

Home away from Home

WalkabilityOutdoor spacesLocation

4.71 out of 5 average rating, 104 reviews

A light-filled living area showcases comfortable seating arrangements, including a plush couch and chair. A large television is positioned on a stylish stand. Hardwood flooring complements the soft color of the walls, creating a welcoming ambiance. Natural light floods in through the bay windows.

Home in Whitby

Bright and Spacious Whole House 5 BR free parking

WalkabilityPetsLocation

4.69 out of 5 average rating, 26 reviews

Home in Ajax

Beautiful Private Detached Home in Ajax!

LaundryHot tubKitchen

4.95 out of 5 average rating, 84 reviews

Home in Ajax

Cheery 1941 Historic Home in Ajax

WalkabilityOutdoor spacesCleanliness

4.83 out of 5 average rating, 72 reviews

Home in Whitby

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

PetsWalkabilityNearby

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.

4.88 out of 5 average rating, 112 reviews

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

Outdoor spacesPetsBeach

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, 142 reviews

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

WalkabilityOutdoor spacesCheckout

4.83 out of 5 average rating, 12 reviews

The exterior of a spacious, detached house is showcased, featuring a light brick façade. A well-maintained lawn and colorful flower beds frame the walkway. The driveway accommodates two cars, with a covered porch area visible, and large windows allowing natural light to filter into the entryway.

Home in Whitby

Big Luxury Detach House For Short And Long Stay

Outdoor spacesPetsGetting around

5.0 out of 5 average rating, 15 reviews

Flat in Unionville

"27" Brand New 3 Bed condo

WalkabilityCheckoutPool

4.96 out of 5 average rating, 25 reviews

A backyard oasis features an inground pool surrounded by lush greenery and colorful flowering plants. Sun chairs are positioned on the lawn, facing the water. The covered seating area above provides shade, enhancing the tranquil outdoor setting.

Flat in Ajax

Oasis by the Lake

Outdoor spacesWalkabilityGetting around

Flat in Oshawa

New place to stay

The Hideaway • 3 BR w/ 3 Ensuites • DT Oshawa

4.96 out of 5 average rating, 254 reviews

The interior features rustic log walls complemented by wooden beams. A dining area is set with a white tablecloth and dark chairs, while a vintage dresser holds decorative items. A minimalist wall art piece depicting a deer adds character to the warm space.

Guest suite in Uxbridge

Mackenzie Cottage

PetsOutdoor spacesBiking

4.9 out of 5 average rating, 104 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

WalkabilityOutdoor spacesSleep quality

Private, pet-friendly home rentals

4.91 out of 5 average rating, 70 reviews

A modern living area is highlighted by a large black sectional sofa adorned with colorful throw pillows. A light wood coffee table sits atop a soft area rug, with a potted plant nearby. Light streams through large windows dressed with stylish shades, creating a bright and inviting space.

Townhouse in Oshawa

Brand New Luxurious 4B Townhouse

WalkabilityIndoor spacesNearby

4.94 out of 5 average rating, 51 reviews

A cozy living area features a soft gray sofa adorned with a light pink throw and an orange pillow. A modern TV is mounted on the wall opposite a white media console. A cheerful yellow accent wall is visible beside a small dining table, creating an inviting space.

Guest suite in Whitby

Keyless | Parking | 2 Q Beds | Toronto Hub | SPA

PetsWalkabilityLong stay

4.96 out of 5 average rating, 24 reviews

Bungalow in Whitby

Executive Retreat/Forest Trails/Golfing/Skating

PetsCheck-inCleanliness

4.94 out of 5 average rating, 33 reviews

A cozy living area features a dark sectional sofa accompanied by a comfortable armchair. A round coffee table sits on a plush rug, and natural light enters through two windows. A flat-screen television is mounted on the wall, with additional lighting provided by a standing lamp.

Flat in Oshawa

Spacious and cozy 1 bedroom professional suite.

PetsWalkabilityNearby

4.98 out of 5 average rating, 41 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!

PetsHeatingCleanliness

4.88 out of 5 average rating, 8 reviews

Flat in Lakeview

Modern 1BR Retreat | Near Oshawa Lakeshore & Beach

ComfortHospitalityIndoor spaces

4.97 out of 5 average rating, 62 reviews

Flat in Oshawa

Double Bedroom Stylish Unit with separate entrance

WalkabilityPetsComfort