Pet-friendly holiday rentals in Southampton

4.99 out of 5 average rating, 411 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! An hour from Toronto.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom 2nd BR bunk beds w/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

4.99 out of 5 average rating, 122 reviews

The exterior of the modern home is shown at dusk, with warm light glowing from windows. A circular fire pit is surrounded by wooden Adirondack chairs, and the lawn is well-maintained. The covered patio is visible, providing ample space for outdoor seating.

Cottage in Kincardine

Kinloft Cottage!

Welcome to the gorgeous beaches of Kincardine, Ontario! Have fun with the whole family at this 4 year old, custom built home! A short walk to the stunning sandy beaches and famous sunsets of Lake Huron (about 9 minute walk) may just have you falling in love with this quiet and peaceful town of Kincardine! A friendly and welcoming community, local dining and quaint shops await you! We are super excited to host you and your family! Great for Contractors or Executives too - 20 min to Bruce Power!

4.94 out of 5 average rating, 143 reviews

A light-filled living area features a comfortable gray sofa and two rattan chairs with cushions. A flat-screen TV is mounted on the wall, and a natural fiber rug lies beneath a white coffee table. Elements of greenery can be seen, adding a refreshing touch.

Cottage in Sauble Beach

COMPLETELY RENOVATED cottage -steps from the Beach

Charming coastal cottage, 2 min walk to the beach and 5 to the main strip. This is a perfect beachside retreat, with new flooring throughout, plank ceilings, fully loaded kitchen with SS appliances and quartz countertops, new bathroom, new mattresses... a large fully furnished patio and fire pit. 2.5 hours outside of TO on the shores of Lake Huron - and fully winterized for year-round getaways! AS SEEN IN HOUSE AND HOME MAGAZINE, JULY 2019! FOLLOW US: @amabelbeachhouse * linens not provided

4.95 out of 5 average rating, 107 reviews

The exterior of a two-story cottage is visible against a bright blue sky, positioned near the shoreline of Lake Huron. A red roof complements the gray-blue siding. A flagpole displays a Canadian flag to the right, while a drive leads to an outdoor space surrounded by greenery.

Cottage in Miller Lake

Lakefront, sauna, sunsets: Alvar Garden Lakehouse

Waterfront cottage located halfway between Tobermory and Lion’s Head, on the shores of Lake Huron. Enjoy a spacious lakefront retreat with shallow, warm waters and spectacular sunsets. This cottage is the perfect gateway for hiking, kayaking, sightseeing, fireside evenings, stargazing, and year-round relaxation — including rejuvenating time in the outdoor sauna. Bruce Peninsula at its best, with major attractions within a 30-minute drive. The perfect base for adventure, water, and sunsets.

Farm stay in Township Of Southgate

An industrial-style apartment features a spacious open living area with a dark leather couch and a wooden coffee table. A staircase leads to an upper sleeping area, while concrete walls provide a modern backdrop. Natural light enters from nearby windows, enhancing the interior space.

4.86 out of 5 average rating, 204 reviews

Loft Where City Meets Country With Hot Tub

This unique place has a style all its own, while situated on a very private 39 acres where city style meets country living. The industrial apartment has been designed inside of a large building and offers all the luxuries of real glamping. Comfort and style throughout, complete with hotel quality mattress and linnens. The forested trails and beautiful property are a nature lovers paradise. You will find everything needed for a perfect getaway rather walking the trails or relaxing by the pond!

Place to stay in Chatsworth

Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.

5 out of 5 average rating, 124 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

4.95 out of 5 average rating, 150 reviews

The exterior of a two-story house is depicted, featuring a combination of blue siding and brick. Soft illumination highlights the windows, providing a warm glow. A green lawn and a tree are visible in the foreground, alongside a vehicle parked in the driveway.

Home in Southampton

Holiday House on Huron

The location is truly special—just a short walk to boutique shops, local cafés, excellent restaurants, and a craft brewery. Whether you're here for the beach, biking the scenic Saugeen Rail Trail, or exploring the charm of small-town life, this is the perfect spot to experience it all. The open concept upper level is designed for gathering, entertaining, or simply unwinding in comfort. Main floor, you’ll find three cozy bedrooms (primary bedroom with ensuite), a full bathroom with bathtub.

4.9 out of 5 average rating, 125 reviews

A spacious living area features a cozy sofa, several stylish chairs, and a rustic coffee table. Light streams in through bright windows, accentuating the blue walls and patterned rug. A dining area with modern chairs and a retro refrigerator adds character to the space.

Cabin in Southampton

Cabin Suite #2 at Driftwood Haus

Pet Friendly! Listen to the waves steps away! All newly renovated with brand new beds and furnishings. Enjoy the freedom. With the second best sunsets in the world according to National Geographic, Southampton is a community on the shores of Lake Huron in Bruce County, Ontario, Canada and close to Port Elgin. It is located at the mouth of the Saugeen River next to the Saugeen Ojibway Nation Territory. We have the most beautiful public beach in Ontario, a natural harbour and 3 lighthouses!

Place to stay in Southgate

A charming A-frame cabin stands amidst lush green trees, with expansive glass doors opening to a wooden deck. Comfortable seating arrangements are present, complemented by planters filled with blooming flowers, creating a serene and inviting outdoor space.

4.99 out of 5 average rating, 280 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin is partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse Sauna & jacuzzi tub available yr round. Note: Wood hot tub replaced in 2025 with jacuzzi spa Cabin heated by wood stove in the winter months and supplemented with a mini split heater. Firewood/kindling provided Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road

4.92 out of 5 average rating, 292 reviews

A serene view of Little Lake is presented, featuring a calm surface reflecting the evening light. A grassy area is framed by a black fence, while a dog gazes toward the water. A sandy beach and dock are visible along the lake’s edge, surrounded by greenery.

Cabin in Lion's Head

Little Lake Lookout: Sauna, Beach, Dock, Dogs!

Escape to Little Lake Lookout! This serene 2-bedroom + loft and 2-bath retreat boasts 170ft of private lakefront on Little Lake. Enjoy stunning views of the Niagara Escarpment and an abundance of nature and wildlife. With all-season amenities and a scenic drive from the GTA and London, this dog-friendly oasis (we're fenced!) is the perfect getaway for making memories. Only 7 minutes from the charming village of Lion's Head. Book now for a truly unique experience! @NorthPawProperties

4.92 out of 5 average rating, 113 reviews

Cottage in Mar

Waterfront Lakehouse | + EV Charger | AC |

Escape to Whiskey Harbour Lakehouse—your dream waterfront retreat on the Bruce Peninsula. This luxurious timber-frame cottage on Lake Huron blends rustic charm with modern comforts: vaulted ceilings, a stunning Muskoka room, lakefront views, and space for couples, families and nature lovers. Explore turquoise waters, star-filled skies and cozy up fireside after a day of adventure. Ideal for romantic getaways, family escapes and unplugged stays in every season.

4.97 out of 5 average rating, 113 reviews

The striking facade of the modern lake house is framed by lush greenery, showcasing large windows and a unique architectural design. A custom pickleball court is visible in the foreground, bordered by flower planters, enhancing the outdoor environment.

Cottage in Meaford

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.

Popular amenities for Southampton pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 108 reviews

The cottage features a modern exterior with a combination of dark siding and light accents, set among tall trees. A spacious wooden deck is visible, furnished with various seating options and a dining table. Lush green grass surrounds the property, enhancing the outdoor setting.

Home in Ripley

The Birdhouse Cottage in Point Clark

4.97 out of 5 average rating, 162 reviews

A charming century home features a blend of red brick and light siding. The entryway is highlighted by a covered porch and decorative star. Lush greenery surrounds the property, adding to its inviting appeal under clear blue skies.

Home in Meaford

Beach & Hiking Nearby • Large Private Fenced Yard

4.95 out of 5 average rating, 197 reviews

A well-lit living area features two comfortable gray sofas adorned with patterned throw pillows. Warm wooden floors complement the neutral wall tones. A staircase with wooden steps leads to the upper level, while large windows allow natural light to brighten the space.

Home in Williamsford

Williamsford Blacksmith Shop

4.98 out of 5 average rating, 106 reviews

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

Birdsong, the perfect Blue Mountains getaway

4.97 out of 5 average rating, 144 reviews

A charming farmhouse is set amidst a lush green lawn, surrounded by mature trees. A white fence complements the landscape. The building features a red door and light grey siding. Two dogs can be seen on the grass, adding a warm touch to the serene country setting.

Home in Grey Highlands

Newly Renovated! Charming Beaver Valley Farmhouse

4.97 out of 5 average rating, 139 reviews

An open and airy space features a large harvest table with pink legs, complemented by wooden chairs. A cozy bench is positioned alongside the table. A staircase leads to a loft area, while art supplies and decor are visible throughout the room.

Home in Desboro

Forest Loft - Forest, Sauna, Ponds & Stargazing

4.85 out of 5 average rating, 313 reviews

A group of individuals enjoys the sunset from a dock, playfully splashing in the water. The warm hues of the setting sun create a serene backdrop, highlighting the joyful atmosphere of the moment by the waterfront.

Home in Mar

Red Bay Getaway

4.99 out of 5 average rating, 100 reviews

Home in Meaford

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 129 reviews

Cottage in Meaford

Cottage on 5 Private Acres, Heated Pool & Hot Tub

5 out of 5 average rating, 6 reviews

An aerial view of the surrounding area highlights the proximity of the Black Horse Motor Inn to the beach. The site features green trees, various cottages, and a heated saltwater pool, with the shoreline visible in the distance.

Cabin in Sauble Beach

Tiny Luxury Cottage - Cottage 1

4.99 out of 5 average rating, 149 reviews

A spacious outdoor area features a picnic table and multiple lounge chairs arranged on well-maintained grass. The wooden structure in the background has large windows, adorned with awnings, and is surrounded by greenery under a clear blue sky.

Farm stay in Markdale

Experience Country Living at Firefly Ridge

4.84 out of 5 average rating, 193 reviews

A rustic cabin is nestled among towering trees, featuring a sloped metal roof and wooden door. A table with benches is positioned in front, accompanied by two Muskoka chairs. Gravel pathways lead to the cabin, enhancing its secluded ambiance.

Hut in Owen Sound

Harper Cabin

4.88 out of 5 average rating, 207 reviews

The kitchen features an open layout with warm wood flooring and a large dining table set for twelve. Natural light enters through two windows beside the door. Stainless steel appliances and a well-equipped countertop complete the functional space.

Home in Kimberley

Heart of Kimberley - with views and a hot tub

4.89 out of 5 average rating, 161 reviews

A cozy bedroom features a spacious bed adorned with a white and blue floral duvet. Warm lighting is provided by bedside lamps on either side of the bed. A tasteful horse artwork is displayed on the wall, complementing the calming blue walls.

Home in Chatsworth

Stonehaven - large country retreat, with pool*

4.98 out of 5 average rating, 244 reviews

The entrance showcases intricate woodwork and architectural details, with a grand staircase leading to the upper level. A large door opens to the outside, and a vintage chandelier illuminates the inviting foyer, highlighting the craftsmanship of the historic home.

Home in Owen Sound

Butchart Estate: Breathtaking Victorian mansion

4.97 out of 5 average rating, 58 reviews

Home in Kimberley

Sweeping Views - Beaver Valley Farmhouse & Pool

Private, pet-friendly home rentals

4.9 out of 5 average rating, 40 reviews

Cottage in Wiarton

Top Rated Waterfront Luxury Cottage | Sauna |Dock

5 out of 5 average rating, 12 reviews

Cabin in Elmwood

Cedar and Fern Cabin | Private Pond Forest Retreat

A serene living area is equipped with a comfortable sofa and accent chair, positioned around a light wood coffee table. A television is mounted on the wall, while a gas fireplace adds warmth. Large windows are dressed with soft curtains, allowing natural light to fill the space.

4.91 out of 5 average rating, 47 reviews

The Dekking House

4.97 out of 5 average rating, 32 reviews

A spacious loft area is seen from the main floor, featuring a sleeping space and a chandelier with candles. Natural wood paneling adorns the walls, and light streams in from large windows. A staircase with a wooden railing connects the two levels.

Home in Wiarton

Charming 1899 Church Haven in Oliphant

5 out of 5 average rating, 48 reviews

A cozy living room features a stone fireplace with a mounted television above it. A light-colored sofa with decorative pillows and a warm throw occupies the space alongside a vibrant orange armchair. A wooden coffee table and a plant add natural elements to the inviting atmosphere.

Cottage in Southampton

Modern, family cottage - a stone's throw to beach

A serene outdoor seating area is illuminated by string lights, offering a view of a sunset over the water. Red Adirondack chairs surround a stone fire pit, framed by lush greenery and a tranquil waterfront landscape.

4.89 out of 5 average rating, 47 reviews

Stay on the Bay

Superhost

4.9 out of 5 average rating, 10 reviews

Moore Escapes Cottage

A tranquil bedroom features soft blue walls with a cloud-like design. A spacious bed is centered, flanked by two bedside lamps. A television and a dresser are present, along with an inviting wooden bench at the foot of the bed. Natural light enters through skylights and windows.