Pet-friendly holiday rentals in Oakville

4.81 out of 5 average rating, 156 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.

WalkabilityOutdoor spacesValue

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, 179 reviews

Frenchman’s Pass - Cozy nook on the Hamilton brow

Welcome to your home away from home! This charming suite at the back of our home has a separate entrance and a convenient private deck. Nestled on the Hamilton Mountain in one of Hamilton's most upscale neighborhoods, we are steps from the scenic brow offering the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking and essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping, restaurants, and public transit.

WalkabilityOutdoor spacesCheckout

4.96 out of 5 average rating, 326 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 AUGUST 30-SEPTEMBER 3 (4 nights/5 days) 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.

PetsOutdoor spacesDecor

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, 192 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.

PetsOutdoor spacesLong stay

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”

PetsOutdoor spacesKitchen

4.83 out of 5 average rating, 106 reviews

Luxurious 4 Bedroom home.

Situated in Oakville, Ontario and backing onto natural green space, the interior of this contemporary home is lavished in natural light and enhanced with panoramic views of sunsets. Located between Toronto and Niagara Falls, this home also offers the combination of convenient access to urban amenities and an array of outdoor attractions for sightseeing, exploration and adventure. A perfect retreat for groups and families seeking comfort, relaxation and roomy collaborative spaces.

Outdoor spacesWalkabilityParking

4.78 out of 5 average rating, 394 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

4.9 out of 5 average rating, 540 reviews

An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.

Cabin in Erin

Cabin stay and play! 10 mins to Canadian Open!

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

Outdoor spacesPetsComfort

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, 110 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 spacesWalkabilityQuiet

4.92 out of 5 average rating, 185 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.

WalkabilityOutdoor spacesKitchen

4.75 out of 5 average rating, 114 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.

PetsWalkabilityCondition

4.91 out of 5 average rating, 153 reviews

Condo in Mississauga

Gorgeous & Modern 2Bed 2Bath Sq1 Condo Corner unit

This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a well equippedand gym and games room. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto

WalkabilityPetsNearby

Popular amenities for Oakville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious living area features a sectional sofa adorned with various cushions, arranged around a glass coffee table. Large windows allow natural light to flood the room, offering views of lush greenery. A decorative wall art piece and a potted plant add to the inviting atmosphere.

4.86 out of 5 average rating, 106 reviews

Outstanding Waterside Retreat - HOT TUB & 2KingBed

WalkabilityPetsDecor

4.92 out of 5 average rating, 106 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

WalkabilityPetsLong stay

A serene bedroom features a plush bed adorned with textured white linens and an arrangement of decorative pillows in varying shades of green. Woven wall plates create an artistic display above the bed. A bedside lamp and wooden nightstand are positioned to enhance the space.

4.94 out of 5 average rating, 204 reviews

Stylish Modern 2 bedroom house across from Beach

WalkabilityPetsCleanliness

4.91 out of 5 average rating, 103 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

WalkabilityOutdoor spacesParking

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.

4.81 out of 5 average rating, 124 reviews

California Chic +Breathe +Unwind +Restore

PetsOutdoor spacesParking

4.96 out of 5 average rating, 282 reviews

The Coastal Cottage

Outdoor spacesPetsHeating

4.92 out of 5 average rating, 156 reviews

An outdoor seating area is shown, featuring a table with a fire pit at its center, surrounded by glass stones. Two wine glasses sit atop the table, with flames gently flickering. A cozy chair with an orange cushion is also visible in the background.

Home in Lincoln

3BR Home: King Suite & Backyard-Close to Wineries

WalkabilityConditionHiking

4.94 out of 5 average rating, 34 reviews

Cottage Style House with Hot Tub

Outdoor spacesBathroomSleep quality

Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 166 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

WalkabilityPetsAccuracy

4.86 out of 5 average rating, 213 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

PetsWalkabilityAccess

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

PetsWalkabilityDecor

4.81 out of 5 average rating, 118 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

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, 174 reviews

Rooftop Pool Condo with CN Tower View

PetsOutdoor spacesDecor

4.88 out of 5 average rating, 154 reviews

Steps to CN Tower/Waterfront | 2BR/2BA + Parking

WalkabilityValueView

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, 143 reviews

Charming Condo w Parking, CN Tower View & Pool

WalkabilityPetsCheck-in

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, 107 reviews

Fort York- Lake View Studio Condo + Indoor Parking

WalkabilityPetsIndoor spaces

Private, pet-friendly home rentals

4.98 out of 5 average rating, 642 reviews

A vibrant sunset is captured with layers of orange, red, and yellow hues across the sky. Silhouetted trees and foliage frame the image, creating a contrasting foreground against the colorful backdrop.

Guest suite in Hamilton

Country Getaway in Puslinch

PetsOutdoor spacesKitchen

5.0 out of 5 average rating, 5 reviews

Apartment in Oakville

Executive 1BD+Den Suite|Perfect for Extended Stay

ValueIndoor spacesLocation

4.93 out of 5 average rating, 67 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

PetsOutdoor spacesHeating

4.89 out of 5 average rating, 93 reviews

Apartment in Oakville

Bright 2 Bedroom Apartment, free parking, Wi-Fi

WalkabilityPetsIndoor spaces

4.63 out of 5 average rating, 16 reviews

Condo in Oakville

Serene Stays - Oakville (3 Bed, 2 Bath, 1 Parking)

CheckoutNearbyWi-Fi

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

WalkabilityBarbecueSleep quality

5.0 out of 5 average rating, 22 reviews

An open-concept kitchen and living area features light hardwood flooring and contemporary furnishings. A white leather sofa complements a wooden coffee table, while a large kitchen island with bar stools is highlighted. A dining table accommodates six, and colorful tile accents add character to the space.

Home in Burlington

Modern Luxury House w/EV Charger & Heated Pool

PetsWalkabilityLayout

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.