Pet-friendly holiday rentals in Oakville

4.8 out of 5 average rating, 158 reviews

A comfortable living area is presented with a dark coffee table and two blue couches adorned with patterned throw pillows. Light blue curtains frame the windows, and a large flat-screen TV is positioned on a black TV stand against the wall.

Guest suite in Oakville

New Studio Unit with Full kitchen in Oakville

This is a 500 square feet Studio unit at the ground level of town house with full kitchen, Full Washroom big screen smart TV, internet and one parking. Nothing is shared, separate entrance to the unitKitchen has utensils, kettle and toaster. All the major stores are under 3 kms. The house situated in the border of Oakville and Mississauga. Just 30 minutes to Toronto and 60 minutes to Niagara. Very clean and brand new place for your stay.Enjoy your stay at this place in a relaxing private space.

Outdoor spacesPetsHeating

4.84 out of 5 average rating, 107 reviews

A bright living area features a spacious sectional sofa and a round ottoman on a patterned rug. Large windows provide natural light and offer views of the outdoors. A decorative fireplace and artwork adorn the walls, enhancing the room’s modern aesthetic.

Home in Hamilton

Optimal Waterside Retreat - HOT TUB 2 King Bed

Welcome to your DREAM home away from home! Nestled on the serene waterfront, this elegant four-bedroom, three-bath haven offers the perfect blend of luxury and comfort for your next getaway. Whether you’re seeking a peaceful escape or an adventure-filled trip, our chic property is designed to exceed your expectations. Ready to experience the ultimate retreat? Book now and prepare for an unforgettable vacation where luxury meets nature. We’re here to ensure your stay is nothing short of perfect!

WalkabilityPetsCheck-in

4.81 out of 5 average rating, 126 reviews

The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.

Home in Hamilton

California Chic +Breathe +Unwind +Restore

Enter through the grand foyer with a winding staircase, pass the kitchen, and step into the relaxing backyard featuring an in-ground, diamond-shaped, solar-heated swimming pool and a stunning lake. The view of the lake is beautiful! The area is quiet and scenic, with the soothing sounds of the lake lulling you to sleep. You are just 30 minutes away from Niagara Falls and 1 hour from Toronto. On a clear day, you can even see the Toronto skyline. It's the perfect place for a group or family of 9.

PetsOutdoor spacesBarbecue

4.96 out of 5 average rating, 328 reviews

The exterior of the guest house features a wrap-around composite deck with glass railing, overlooking the direct waterfront views of Lake Ontario. The structure is surrounded by lush greenery and is complemented by large windows allowing natural light into the living space.

Guesthouse in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS SEPTEMBER 1 (1 night/2 days) SEPT 7-11 OCTOBER 18-21 (3 nights) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards & direct Lakefront

Outdoor spacesWalkabilityParking

A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.

4.89 out of 5 average rating, 193 reviews

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ

Bring your friends and family to this family-friendly, centrally-located neighbourhood with lots of room for fun and find a home away from home during the travelling. Enjoy your stay in this licensed short-term accommodation for a modern, luxurious, and spacious three-bedroom and two-bathroom detached home with a huge backyard: watching a movie and cozying up by the fire, enjoying the company of friends and family seated around the dining table, or simply in between moving or renovations.

WalkabilityOutdoor spacesBarbecue

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

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Outdoor spacesPetsLocation

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

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

WalkabilityPetsLaundry

4.79 out of 5 average rating, 396 reviews

A modern living area is showcased with large windows, allowing natural light to fill the space. A colorful yellow sofa and blue chairs provide seating. An entertainment unit features a television against a vibrant mural of cacti. Wooden flooring adds warmth to the contemporary design.

Hotel room in Hamilton

Fully-Furnished Boutique 1 Bedroom Suites

The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.

WalkabilityPetsWi-Fi

A spacious room features a modern geometric accent wall in various shades of blue, yellow, and green. A neatly made bed with soft linens is centered in the area, flanked by two bedside tables and lamps. A workstation with a comfortable chair is visible in one corner.

4.85 out of 5 average rating, 113 reviews

Family Home | Uptown Oakville | 40 Mins to Toronto

If you're looking for a stylish and comfortable home-away-from-home experience, you've come to the right place! We're in the heart of uptown Oakville, close to tons of restaurants, grocery stores, coffee shops and salons. 10mins to Oakville Place, 6mins to Sheridan College and 5mins to the 5-Drive In - an outdoor drive-in theatre perfect for family outings or date night! Our home is fully equipped with everything you need for a comfortable stay. We think you'll love it here :)

Outdoor spacesWalkabilityAmenities

4.92 out of 5 average rating, 108 reviews

An open-concept living area features a sleek electric fireplace beneath a mounted Smart TV. Two round tables with colorful chairs provide seating, while natural light enters through windows adorned with elegant coverings. A modern coffee table sits in front, completing the cozy ambiance.

Home in Milton

Spacious 2 BR apartment | Glen Eden Ski

Escape to our cozy 2-bedroom basement apartment, minutes from Milton’s downtown, 500m from No Frills, and just a 10-minute drive to Toronto Premium Outlets. Perfect for travelers, this inviting retreat is close to both nature and city attractions. Explore nearby Glen Eden Ski Resort and Rattlesnake Point Conservation Area, or enjoy easy access to Oakville, Burlington, Mississauga, and Toronto. Ideal for work or leisure, it offers the perfect mix of comfort and convenience.

WalkabilityPetsBathroom

4.92 out of 5 average rating, 186 reviews

The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.

Villa in Burlington

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

Outdoor spacesPetsHot tub

4.75 out of 5 average rating, 116 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

WalkabilityPetsAccuracy

Popular amenities for Oakville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 108 reviews

A light-filled living area features a plush, beige sofa and armchairs arranged around a coffee table. A mirrored wall decoration reflects light, while a decorative chandelier hangs above. The space leads to a staircase and an entrance door with a decorative mirror nearby.

Home in Waterdown

Ninos Place

PetsWalkabilityQuiet

4.83 out of 5 average rating, 104 reviews

Home in Burlington

Centrally Located, Walk to Lake, Spacious | SH

PetsWalkabilityNearby

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 spacesPetsNearby

5.0 out of 5 average rating, 23 reviews

Executive Townhouse Oakville

WalkabilityLaundryParking

4.89 out of 5 average rating, 36 reviews

Cottage Style House with Hot Tub

Outdoor spacesCheck-inAccess

4.8 out of 5 average rating, 30 reviews

The Oakville Comfort and Modern Stay

Outdoor spacesWalkabilityCheck-in

A modern living area features a grey sectional sofa positioned against a wall with large windows, providing ample natural light. A textured rug covers the hardwood floor, while a coffee table with decorative items is centered in the space. A green plant adds a touch of nature.

4.77 out of 5 average rating, 61 reviews

Modern & Luxury Townhouse in Oakville

LayoutGetting aroundParking

5.0 out of 5 average rating, 26 reviews

The entrance of a bungalow is framed by a covered porch adorned with climbing greenery. Two chairs are placed beside a small planter, while seasonal decorations accentuate the front door. Steps lead up to the door, surrounded by colorful potted flowers.

Home in Bronte

Maia's cozy Bronte cottage by the Lake

WalkabilityOutdoor spacesValue

Pet-friendly home rentals with a pool

4.82 out of 5 average rating, 119 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 spacesWalkabilityComfort

4.87 out of 5 average rating, 217 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.

Condo in Mississauga

Beautiful Penthouse with Breathtaking View

PetsWalkabilityFamily

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

PetsWalkabilityBathroom

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, 180 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

WalkabilityPetsHot tub

4.96 out of 5 average rating, 153 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

WalkabilityPetsSkiing

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.

4.94 out of 5 average rating, 147 reviews

Charming Condo w Parking, CN Tower View & Pool

WalkabilityPetsSleep quality

Condo in Downtown Toronto

A desk with an ergonomic chair is positioned near floor-to-ceiling windows, offering a stunning view of Lake Ontario at sunset. The scene features a vibrant sky with hues of orange and purple, along with glimpses of the surrounding greenery and cityscape.

4.98 out of 5 average rating, 108 reviews

Fort York- Lake View Studio Condo + Indoor Parking

WalkabilityPetsHospitality

Apartment in Liberty Village

A modern living space is captured with a large window offering expansive city views. A cozy green sofa is paired with decorative pillows, positioned on a patterned area rug. A round mirror and a stylish floor lamp are included, enhancing the space's contemporary design.

4.89 out of 5 average rating, 100 reviews

Summerlicious - Vibing Liberty Village

WalkabilityPetsValue

Private, pet-friendly home rentals

4.92 out of 5 average rating, 203 reviews

The image captures a serene view of the lakeside property, featuring a lush green lawn that slopes towards Lake Ontario. A sandy beach area and rocky shoreline are visible, framed by trees on both sides and calm turquoise water reflecting the clear sky.

Cottage in Hamilton

Lake Front Heaven - Gateway to Niagara/Vineyards

WalkabilityOutdoor spacesSleep quality

4.92 out of 5 average rating, 228 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

Outdoor spacesWalkabilityFamily

4.84 out of 5 average rating, 231 reviews

The open-concept living area showcases a comfortable gray sofa and armchairs, complemented by a wooden coffee table atop a patterned rug. Bright overhead lighting enhances the spaciousness, while a dining table is visible in the background. Wall art adds a touch of personality to the modern surroundings.

Guest suite in Brampton

Studio 8848 | 3BR+2BATH | Sleeps 8

PetsTVFamily

Place to stay in Hamilton

An open-concept living area features a cozy sectional sofa and a coffee table. A wall-mounted TV is positioned above a contemporary fireplace. Natural light is welcomed through sliding glass doors that lead to a private outdoor space, offering a sense of comfort and relaxation.

4.86 out of 5 average rating, 181 reviews

Frenchman’s Pass - Cozy nook on the Hamilton brow

PetsWalkabilityLaundry

4.93 out of 5 average rating, 68 reviews

A spacious living area is furnished with a dark sofa and light wooden tables. A large television is positioned on a media console. Natural light enters through a window and glass doors, which lead to the backyard. A textured area rug adds warmth to the room.

Guest suite in Oakville

Spacious 2 bedroom walkout basement suite

WalkabilityOutdoor spacesQuiet

5.0 out of 5 average rating, 5 reviews

Apartment in Oakville

Executive 1BD+Den Suite|Perfect for Extended Stay

ParkingComfortLocation

4.78 out of 5 average rating, 79 reviews

A two-story detached house is shown, featuring a light beige exterior with a prominent balcony on the upper level. The garage entrance is visible, along with a driveway accommodating two vehicles. Lush green shrubs and a well-kept lawn enhance the front yard, under a partly cloudy sky.

Apartment in Oakville

Apartment unit

WalkabilityValueAccuracy