Pet-friendly holiday rentals in Oakville

4.86 out of 5 average rating, 129 reviews

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.

Apartment in Hamilton

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.

4.9 out of 5 average rating, 244 reviews

A spacious bedroom features a large bed adorned with white linens and decorative pillows. A textured basket holds towels beside the bed. A patterned throw blanket is draped over a wooden bench at the foot of the bed. A dark blue accent wall adds depth to the serene space.

Home in Hamilton Beach

Beautiful Renovated Beach Cottage Home

When you enter our immaculately clean Beach Cottage home you will feel like you are at a boutique hotel. Beautiful white linens and towels, WIFI, smart TV, Keurig coffee machine and more. Choose to have a BBQ with friends and family on one of our two decks as you watch the Sunset from Lake Ont. Take a stroll or a bike ride down the Beautiful boardwalk or visit the beautiful beach all located at the end of our yard. Whether you are here for business or pleasure there is something for everyone!

4.89 out of 5 average rating, 221 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.

4.89 out of 5 average rating, 182 reviews

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.

Home in Oakville

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.

4.89 out of 5 average rating, 130 reviews

A modern two-story house is set against a green backdrop, featuring large windows that allow natural light to flood the interiors. The driveway leads to an attached garage, while a neatly maintained lawn surrounds the property, enhancing its curb appeal.

Home in West Oakville

Large Luxury Villa with Swim Spa! Near downtown!

Forget your worries in this spacious, serene and unique house! Large backyard with a Swim Spa to enjoy! Backyard filled with fire places! 6 Bedroom, 7 beds, 4 full baths, 4 offices, 3 family rooms, 9 TV, equipped kitchen, patio, board games, BBQ grill, fire place, Tesla charger. Quiet yet central from downtown Oakville, highways, groceries, shopping, bars, restaurants, cafe's and much more! Always professionally cleaned. For elderly guests a bedroom and full bath is on ground floor.

4.9 out of 5 average rating, 510 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

Erin Cabin Getaway and Bunkie

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!

4.96 out of 5 average rating, 314 reviews

Home in Port Dalhousie

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

License 23 110691 STR. Enjoy extraordinary sunsets and views of Lake Ontario and the Toronto Skyline while sitting in comfortable Muskoka chairs around a fire pit, enjoying a cup of coffee or a glass of wine. My home offers high-speed internet, multiple Smart HD TVs, indoor fireplace, 2 outdoor fire pits, and a large backyard with stairs leading to a Private Beach. Just a short walk to Lakeside Beach, downtown Port Dalhousie, and a short drive to Niagara wineries!

4.97 out of 5 average rating, 292 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 MAY 5-8 (3 nights/4 days) MAY 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: lakefront and orchards.

4.83 out of 5 average rating, 290 reviews

A spacious living area features a dark leather sofa and a wooden coffee table at its center. A framed winter landscape hangs on the wall, while two lamps provide soft lighting. In the background, a dining counter with stools is visible, leading to the kitchen.

Townhouse in Burlington

The Best of Downtown Burlington - Safe & Clean

Experience the magic of downtown Burlington voted Canada's best city to live your stay allows you to walk no more then 10 minutes to Award Winning Restaurants, Spencer Smith Park, Joseph Brant Hospital, and so much more. Get cozy in a self contained townhouse unit that's quiet, clean, safe, with free parking and a dog friendly fully fenced in backyard. All guests wishing to book must provide a valid first and last name. I'm sorry cats are not permitted

4.94 out of 5 average rating, 170 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.

4.9 out of 5 average rating, 134 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

4.84 out of 5 average rating, 123 reviews

The kitchen area includes white cabinetry and a stainless steel stove. A dining table with dark wooden chairs is positioned in front of a wall-mounted TV. A patterned rug covers the tiled floor, while a doorway leads to another room.

Apartment in Oakville

Cozy basement apartment in the heart of Oakville

Enjoy a comfortable two bedroom apartment in a quiet, safe neighborhood. Private entrance leads to 2 bedroom basement apartment with a queen and a double bed with Full kitchen. Very close to Sheridan College, Go Train, and Oakville Place mall. Quiet, many parks and trails nearby, public transit. Fully furnished, stainless steel fridge, air conditioning. Pet friendly, no smoking/vaping.

Popular amenities for Oakville pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.82 out of 5 average rating, 11 reviews

3 bedroom home close to downtown with Pool!

4.87 out of 5 average rating, 216 reviews

Home in Caledon

Studio Apartment

4.92 out of 5 average rating, 53 reviews

A modern living room features a spacious sectional sofa accompanied by two stylish armchairs. A minimalistic coffee table is centered on a soft area rug. Light flows in from a large window, while framed artwork enhances the neutral color scheme of the room.

Home in Oakville

Bright & Stylish 5 BR Modern Getaway!

4.94 out of 5 average rating, 162 reviews

A private outdoor space is highlighted by a spacious hot tub surrounded by wooden decking. Nearby, two red Adirondack chairs invite relaxation. Lush greenery and trees provide a natural backdrop, creating a serene environment ideal for unwinding.

Home in St. Catharines

Niagara Wine Country Art House | Hot Tub | 2 ppl

A large glass door opens to a spacious wooden deck, inviting natural light into the indoor space. The deck features a wooden railing adorned with lush plants. Bright blossoms and outdoor seating create a welcoming atmosphere, framed by trees and a clear blue sky.

5 out of 5 average rating, 31 reviews

Charming retreat with lake view

4.89 out of 5 average rating, 153 reviews

A modern bedroom features a spacious bed framed by two bedside tables and a lamp. A sleek black sofa sits beside a circular coffee table adorned with a bouquet of flowers. Subtle artwork and neutral walls create a calming atmosphere.

Home in Milton

Private Suite. Milton New Modern Basement Suite

4.89 out of 5 average rating, 87 reviews

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.

Home in Oakville

2026 FIFA |40 Mins to BMO Field |Oakville GO Train

5 out of 5 average rating, 7 reviews

An expansive open-concept living area features large windows allowing natural light to fill the space. A dark leather sectional sofa complements a glass coffee table, while a dining area with stylish chairs is arranged nearby. A modern kitchen with stainless steel appliances can be seen in the background.

Home in Lakeview

Bright Corner Townhouse - Lakeview

Pet-friendly home rentals with a pool

4.86 out of 5 average rating, 204 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

4.97 out of 5 average rating, 113 reviews

A dining table with a circular glass top and four black chairs is positioned near large windows, offering expansive views of the Toronto skyline. A small potted plant adds a touch of greenery, while natural light fills the space, enhancing the modern interior.

Apartment in Fort York

The Farmer's Cottage

Apartment in Harbourfront

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, 153 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

Condo in Humber Bay Shores

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.

4.81 out of 5 average rating, 115 reviews

Humber Bay Family Friendly condo w Terrace&Parking

4.96 out of 5 average rating, 146 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

4.98 out of 5 average rating, 104 reviews

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.

Condo in Fort York

Beautiful Lake View Studio Condo + 1 free Parking

Condo in Entertainment District

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, 126 reviews

Charming Condo w Parking, CN Tower View & 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.

4.94 out of 5 average rating, 127 reviews

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

Private, pet-friendly home rentals

5 out of 5 average rating, 20 reviews

Home in Mississauga

Sheridan Park Luxury Home

A serene view of the Creek Side Cottage, showcasing a charming blue exterior surrounded by lush greenery. The gently flowing Grindstone Creek runs alongside the property, with a spacious lawn extending towards the water. The natural landscape adds to the tranquil atmosphere.

4.78 out of 5 average rating, 49 reviews

Creek Side Cottage - Hot tub, hiking, games

4.96 out of 5 average rating, 46 reviews

A spacious seating area features a light grey sectional sofa adorned with plaid blankets and decorative pillows. A Christmas tree is positioned in the corner, softly lit with warm lights. Blackout curtains frame a window, contributing to a cozy ambiance.

Guesthouse in Milton

Modern Loft with Immersive Theatre Experience

4.96 out of 5 average rating, 49 reviews

A vibrant living space showcases a bright yellow sectional couch in the foreground, with decorative cushions. A fireplace with a playful pink design is accented by silver spheres, while colorful murals and plants add to the lively ambiance. A dining area with artistic touches is visible beyond.

Bungalow in Hamilton

Colourful House with Private Yard

4.76 out of 5 average rating, 67 reviews

A bright living room features a modern sofa, accent chairs, and a large coffee table. A colorful wall art piece adds a lively touch above the sofa. A cozy fireplace is positioned against a textured wall, while light streams in through window treatments.

Townhouse in Oakville

House of 3 Bed 3 Wash-Crib-King Bed-85' TV-Wrkspce

4.95 out of 5 average rating, 83 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

4.96 out of 5 average rating, 73 reviews

A hot tub is illuminated with a soft pink light, surrounded by a wooden deck. A private entrance to the home is visible in the background, complemented by greenery and a clear evening sky.

Home in Hamilton Beach

Panoramic Lake Views | Hot Tub • Beach • Firepit

A modern living room features a gray sofa paired with a decorative throw pillow. A wooden coffee table sits on a colorful area rug. A flat-screen TV is mounted on the wall, and a decoratively placed light fixture illuminates the space, while a stone fireplace adds a cozy touch.