Pet-friendly holiday rentals in Oakville

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.

4.8 out of 5 average rating, 164 reviews

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 spacesPetsGetting around

4.83 out of 5 average rating, 110 reviews

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.

Home in Hamilton

Lovely Waterfront Getaway - HOT TUB & 2King 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!

PetsWalkabilityKitchen

4.96 out of 5 average rating, 331 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 OCTOBER 1 (1 night/2 days) discounted price for this one night 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 spacesParking

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, 194 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.

WalkabilityPetsPool

4.83 out of 5 average rating, 109 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.

WalkabilityPetsAmenities

4.9 out of 5 average rating, 169 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.

PetsWalkabilityCleanliness

4.79 out of 5 average rating, 403 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.

WalkabilityPetsLocation

4.92 out of 5 average rating, 206 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

A magical cottage with its own beach house on Lake Ontario. This place is special! The beach house an extra bedroom and full bath which is available during the spring/summer months. There’s a pier, boat slip, fire pit, picnic table and plenty of outdoor seating. All of this 50 minutes from downtown Toronto, 40 minutes from YYZ International airport and 25 minutes from the world famous Niagara falls. The scenic is a great base to explore the Niagara region. Operator License 24-305205

Outdoor spacesWalkabilityQuiet

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, 115 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 spacesPetsParking

4.91 out of 5 average rating, 110 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.

WalkabilityPetsDecor

4.92 out of 5 average rating, 188 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 spacesValue

4.89 out of 5 average rating, 159 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

PetsWalkabilityAccuracy

Popular amenities for Oakville pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 111 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

Outdoor spacesPetsParking

4.76 out of 5 average rating, 119 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

Outdoor spacesWalkabilityValue

4.99 out of 5 average rating, 111 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 spacesWalkabilityHospitality

4.9 out of 5 average rating, 107 reviews

Home in Brampton

The Urban Nest

WalkabilityPetsBackyard

4.83 out of 5 average rating, 138 reviews

A spacious backyard is accented with colorful Adirondack chairs arranged around a fire pit. Lush green grass and trees provide shade, while blooming flowers add natural beauty. A small shed is visible in the corner, contributing to the inviting outdoor setting.

Home in Hamilton

Beachfront 6BR Newly Finished Home - Prof Cleaned

PetsWalkabilityIndoor spaces

4.94 out of 5 average rating, 36 reviews

Cottage Style House with Hot Tub

Outdoor spacesTVAir conditioning

4.78 out of 5 average rating, 32 reviews

The Oakville Comfort and Modern Stay

WalkabilityOutdoor spacesAmenities

A modern living area is furnished with two blue accent chairs and a sleek coffee table. A wall-mounted television is positioned above a contemporary fireplace, creating a cozy focal point. Natural light enters through large windows, enhancing the clean and airy ambiance.

5.0 out of 5 average rating, 88 reviews

Modern 4-Bed Townhome with Cinema & Roof Terrace

Outdoor spacesKitchenAccuracy

Pet-friendly home rentals with a pool

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.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

PetsWalkabilityNearby

4.89 out of 5 average rating, 116 reviews

4.86 out of 5 average rating, 219 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

WalkabilityPetsLong stay

4.82 out of 5 average rating, 122 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

WalkabilityOutdoor spacesAccess

4.96 out of 5 average rating, 154 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

PetsOutdoor spacesHot tub

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.

Rooftop Pool Condo with CN Tower View

Outdoor spacesWalkabilityAmenities

4.94 out of 5 average rating, 178 reviews

Apartment in Downtown Toronto

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.

The Farmer's Cottage

Outdoor spacesWalkabilityKitchen

4.98 out of 5 average rating, 137 reviews

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.

Charming Condo w Parking, CN Tower View & Pool

WalkabilityPetsCheck-in

4.94 out of 5 average rating, 150 reviews

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.

Fort York- Lake View Studio Condo + Indoor Parking

PetsWalkabilityHospitality

4.98 out of 5 average rating, 110 reviews

Private, pet-friendly home rentals

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.

4.93 out of 5 average rating, 73 reviews

Spacious 2 bedroom walkout basement suite

PetsOutdoor spacesHospitality

4.59 out of 5 average rating, 17 reviews

Condo in Oakville

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

AccuracyComfortHospitality

4.75 out of 5 average rating, 20 reviews

Bright & Spacious 3Br/2Bth Suite Private Entrance

Outdoor spacesValuePool

4.77 out of 5 average rating, 35 reviews

Everest Luxury In Oakville

Outdoor spacesBarbecueQuiet

4.95 out of 5 average rating, 20 reviews

Luxury Brand New Private Home 4500 sq feet13 Guest

AmenitiesConditionCheck-in

4.79 out of 5 average rating, 80 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

PetsWalkabilityQuiet

4.78 out of 5 average rating, 51 reviews

The exterior of a two-story home is showcased, featuring a combination of brick and siding materials. Large windows allow natural light to enter, and a well-maintained front pathway leads to the entrance. Neat landscaping includes small shrubs, providing a welcoming appearance.

Home in Milton

Home far away from home

LaundryCheck-inQuiet