Pet-friendly holiday rentals in Milton

4.97 out of 5 average rating, 371 reviews

A chestnut horse stands near a wooden fence, gazing towards the camera. The background features a hazy sunrise, casting a warm glow over the field and creating a tranquil atmosphere.

Tiny home in Action

Farmview Sunrise Cabin located at Molinaro Farm

Welcome to our Farmview Sunrise tiny cabin that is nestled in the middle of our private oasis located in Acton ON. Our 50 acre farm has spectacular views from every direction. Our horses, sheep, swans, ducks, chickens and miniature goats are here to greet you as well. This unique space will allow you to enjoy the beautiful outdoors during the day and a cozy warm space in the evenings. We offer a complementary breakfast for our guests. Our in house chef can also accommodate vegan/plant based

PetsWalkabilityBreakfast

4.83 out of 5 average rating, 106 reviews

Home in Oakville

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.

WalkabilityPetsKitchen

4.78 out of 5 average rating, 393 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.

WalkabilityPetsCheckout

4.9 out of 5 average rating, 539 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!

WalkabilityPetsAmenities

4.99 out of 5 average rating, 426 reviews

A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.

Cabin in Arthur

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side!.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom and queen bed in aw/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly!

PetsOutdoor spacesCheckout

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

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.

PetsWalkabilityLong stay

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.

Guest house in Lincoln

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS AUGUST 17-23 (6 nights/7 days) SEPTEMBER 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.

WalkabilityPetsLocation

4.99 out of 5 average rating, 102 reviews

Cabin in Guelph/Eramosa

Fern Hill Cabin

Escape to a hand-built Amish timber cabin on a peaceful 6-acre farm. Surrounded by willow trees, sheep, pigs, chickens, and a 150-year-old barn. It's your own country-spa retreat! Swim in the spring-fed pond, relax in the beautiful wood burning sauna, stargaze at night, and enjoy a compostable toilet with an unforgettable view! Restored century-old windows let in soft light and rustic charm. Ideal for anyone seeking quiet, nature, and a breath of fresh air.

Outdoor spacesPetsHospitality

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.

Outdoor spacesPetsAccuracy

4.98 out of 5 average rating, 260 reviews

Home in Elora

Private Elora Studio Downtown

Located 3 short blocks from the Elora Mill this charming studio apartment is located in the heart of Elora, across from Bissell Park. The Studio Apartment is in a separate, private building at the back of the property which has a private entrance, private front deck and private garden area along with a parking spot for one vehicle. The wifi has recently been upgraded to the EERO mesh system to help connect you to work and leisure activities.

Outdoor spacesPetsParks

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.

Outdoor spacesWalkabilityQuiet

4.93 out of 5 average rating, 290 reviews

A single-story cottage features a wooden exterior with large windows and a black roof. A path of gravel leads to the entrance, which is framed by greenery and stones. Surrounding the building, the landscape showcases well-maintained grass and a young tree.

Farm stay in Hamilton

Somerset Cottage at West Avenue Cider House

Welcome to West Avenue Cider! During Summer 2018 we renovated an existing outbuilding on the property into a 3 bedroom cottage for guests who are visiting the Cider House and who are visiting the Hamilton area. It’s light filled and spacious and we hope you will get to spend some time with us. The cidery can be a busy spot on weekends during the summer and fall, less busy for our winter guests.

Outdoor spacesWalkabilityNearby

Popular amenities for Milton pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.91 out of 5 average rating, 102 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

PetsWalkabilityAmenities

4.96 out of 5 average rating, 158 reviews

An expansive wooden deck features built-in seating and a sunken fire pit. The space is complemented by a BBQ station with a retractable cover, surrounded by lush greenery. A series of red outdoor chairs invite relaxation while the sky showcases a mix of clouds and sunlight.

Home in Kitchener

LUX 4BR• Theatre Room • Chef Kitchen • Unique Deck

Outdoor spacesWalkabilityWifi

4.99 out of 5 average rating, 155 reviews

Home in Guelph

The Hat Maker's house near University of Guelph

WalkabilityPetsLocation

4.99 out of 5 average rating, 119 reviews

The exterior of a century home is highlighted, featuring a welcoming porch surrounded by lush greenery. A paved driveway leads to the entrance, with neatly trimmed grass and decorative landscaping enhancing the inviting appeal.

Home in Brant

Paris Oasis-The Maples on Brock

Outdoor spacesWalkabilityLong stay

4.96 out of 5 average rating, 119 reviews

A comfortable seating area is showcased with a dark leather couch and a wooden coffee table. Natural light filters through two large windows, revealing views of the serene pond and lush greenery outside. The room is complemented by framed photographs on the wall.

Home in Kitchener

Cottage In The City

WalkabilityOutdoor spacesCondition

4.84 out of 5 average rating, 109 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

Family Home | Uptown Oakville | 40 Mins to Toronto

Outdoor spacesPetsAccess

4.94 out of 5 average rating, 204 reviews

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.

Home in Hamilton

Stylish Modern 2 bedroom house across from Beach

WalkabilityOutdoor spacesGrill

4.97 out of 5 average rating, 891 reviews

A charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.

Home in Elora

Elora Heritage House

PetsOutdoor spacesAccess

Pet-friendly home rentals with a pool

Guest house 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, 112 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

PetsWalkabilityValue

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.

Guest house in Erin

The Captain's Cottage at Willow Pond

PetsOutdoor spacesAmenities

4.97 out of 5 average rating, 222 reviews

Guest house in Breslau

House on the Hill

Outdoor spacesWalkabilityTV

4.85 out of 5 average rating, 272 reviews

A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.

Apartment in Mississauga

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

PetsWalkabilityLocation

4.98 out of 5 average rating, 141 reviews

Guest suite in Kitchener

The Oasis

Outdoor spacesPetsIndoor spaces

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.

Apartment in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

PetsWalkabilityAmenities

4.99 out of 5 average rating, 185 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

PetsWalkabilityAccuracy

4.96 out of 5 average rating, 130 reviews

The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.

Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

WalkabilityOutdoor spacesComfort

Private, pet-friendly home rentals

4.89 out of 5 average rating, 176 reviews

An inviting entrance is framed by two large trees and a wooden structure. A set of steps leads to a wooden deck, adorned with a potted plant. Natural stone borders the area, enhancing the connection to the surrounding greenery.

Barn in Lincoln

Contemporary Vineyard Barn on the Water + Hot tub

WalkabilityPetsLayout

4.94 out of 5 average rating, 199 reviews

The historic log cabin from the 1850s is surrounded by lush greenery. A covered porch with wooden beams invites relaxation, while hanging flower baskets add subtle color. The peaked roof and wooden siding emphasize the cabin's rustic charm in a serene forest setting.

Cabin in Erin

1850 Settler's Cabin in Private Forest

Outdoor spacesPetsEV charging

4.81 out of 5 average rating, 155 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

WalkabilityOutdoor spacesLong stay

4.99 out of 5 average rating, 237 reviews

The interior of the cabin features warm wooden walls and a cozy woodstove. Two blue lounge chairs are positioned near a rustic table. Natural light floods through a large window, illuminating the space, while a striped rug adds comfort underfoot.

Tiny home in Schomberg

SNAKE CABIN(rustic, 'off-the-grid')

Outdoor spacesWalkabilityAmenities

4.86 out of 5 average rating, 159 reviews

A charming wooden Bunkie is nestled among lush greenery. The front porch features a small wooden deck with two red chairs and a round table. Large windows allow natural light to illuminate the interior while the door is framed by a welcoming entry.

Cabin in Caledon East

Bunkie in the Forest

WalkabilityOutdoor spacesView

4.83 out of 5 average rating, 228 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

PetsDecorValue

4.96 out of 5 average rating, 503 reviews

A cozy living room features a mix of dark and light furnishings, including a large sofa and an accent seating area. Natural light streams through multiple windows, illuminating the space. A TV is mounted above a decorative fireplace, accompanied by a coffee table made from reclaimed wood.

Guest house in Elora

Wrights Coach House

Outdoor spacesPetsFamily