Family-friendly vacation rentals in Lion&#x27;s Head

4.98 out of 5 average rating, 167 reviews

The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.

Tiny homes in Kimberley

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

4.99 out of 5 average rating, 158 reviews

The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.

Yurt in Meaford

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

4.94 out of 5 average rating, 172 reviews

A cozy cottage exterior features a gray siding with a welcoming front deck. Sunlight reflects off large windows, offering views of the surrounding landscape. The property is accented by a landscaped area with stones and plants, emphasizing a well-maintained appearance.

Cottage in Lion's Head

Trails End Family Friendly Beach House

Inviting couples and families looking for a relaxing vacation, enjoying beach days, scenic hikes, and stargazing nights. This 3-bedroom beach house is just one street from the sandy beach and playground. Sip your morning coffee on the deck, BBQ in the evenings, and end your day roasting marshmallows at the backyard fire pit under magical dark skies. Hike to the famous lookout. Walk to shops, restaurants, and groceries in minutes. Perfect location for daytripping around the Bruce Peninsula. ✨

4.93 out of 5 average rating, 233 reviews

The exterior features a well-maintained yard with lush green grass surrounding a tree stump and a fire pit, creating a relaxing outdoor space. A red grill is positioned next to the entrance of the stone-clad house, and string lights add subtle illumination.

Guest suite in Wiarton

Cozy Getaway on the Bruce Trail!

Newly renovated, this spectacular and spacious two floor unit comes equipped with everything you need for a perfect getaway to the Bruce! This 3 acre property is conveniently located on the Niagara Escarpment with access to the Bruce Trail through the backyard, Only a 5-minute walk to downtown Wiarton or Georgian Bay. A 20-minute drive from Sauble Beach, and only 45 minutes to Tobermory. You won’t need to travel far from this central location to enjoy all the beauty this area has to offer!

4.95 out of 5 average rating, 171 reviews

A charming barn conversion is pictured, with a unique stone exterior and a distinct blue and gray metal roof. A welcoming entrance is highlighted by a red door and a covered porch. The surrounding yard is adorned with greenery and autumn leaves.

Barn in Lion's Head

The Stone Barn @ Lion's Head

Explore winter on The Bruce Peninsula! Discover our charming 1920s barn conversion, nestled in the heart of the Bruce Peninsula. This cozy retreat accommodates up to 5 guests in 3 spacious bedrooms. Unwind in the inviting living room, prepare meals in the fully-equipped kitchen, and gather around the outdoor fire pit. Explore nearby attractions, including Georgian Bay, Bruce Trail, Lion's Head, Tobermory, and Bruce Peninsula National Park. Book now for a memorable stay! Permit #STA-2024-248

4.99 out of 5 average rating, 125 reviews

The exterior of the cottage showcases a welcoming covered front deck framed by vibrant greenery. A sturdy wooden staircase leads to glass doors. The space features modern outdoor seating with bright yellow accents, surrounded by well-maintained gravel and flower arrangements.

Home in Wiarton

Huckleberry’s Hideaway (Sauna, Starlink Internet)

Relax and enjoy the true cottage lifestyle with a clean, restful and modern feel. Perfect spot to enjoy a peaceful getaway warming up in the Sauna or around the fireplace. Centrally located on the Bruce Peninsula to Tobermory and Sauble Beach. Lovely views of Berford Lake with a public beach only 10 min drive away. Family friendly or couples getaway - we’ve got you covered. Cozy interior, with lots of parking, beautiful covered front decking. BBQ, campfires, Sauna you name it - it’s here.

4.96 out of 5 average rating, 248 reviews

A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.

Guest suite in Kimberley

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

4.96 out of 5 average rating, 123 reviews

A charming A-frame cabin is surrounded by tall trees, featuring a triangular roof and wooden siding. The entrance includes a white door with a window above, complemented by a small wooden deck with stone accents.

Cabin in Clarksburg

Tiny A-Frame near the Bruce Trail

Find yourself nestled among white pine trees just steps off the Bruce Trail! This tiny A-Frame is 100 sq.ft providing enough room for cozy comfort. The cabin is equipped with 2 stackable twin beds converting into a queen bed when desired. Our amenities contain all the essentials, including a BBQ, drinking and dish water, and an outhouse with a composting toilet. Centrally located to Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

4.92 out of 5 average rating, 262 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

4.94 out of 5 average rating, 231 reviews

A traditional Mongolian yurt features a white exterior adorned with blue patterns, supported by wooden poles. Two wooden adirondack chairs sit on a circular stone patio, inviting relaxation in the natural surroundings, with trees visible in the background.

Yurt in Priceville

Natural Mongolian Yurt on Biodynamic Farm and Spa

The yurt is located on our 200 acre biodynamic farm in beautiful West Grey. Guest are welcome to walk around the property and enjoy being in nature. A cozy insulated space available all year round. This accommodation is rustic with outhouse (composting toilets), an outdoor shower and wash basin. Farm experience is also available. Snowshoeing or skiing trails are nearby or on the farm. The Spa (hot tub and sauna) is only available for private bookings for an additional fee.

4.94 out of 5 average rating, 301 reviews

A charming porch area is depicted, featuring a macramé swing chair hung beside a white door. The door displays textured glass panels and is complemented by a black wall lantern. Warm wooden decking enhances the inviting entrance.

Guest suite in Meaford

The Beach Button

Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!

4.96 out of 5 average rating, 131 reviews

A cozy dining area is highlighted by warm wooden walls and a small table set for two. A black propane fireplace provides warmth, while cooking essentials are organized on the counter. A minimalist sink is positioned nearby, adding functionality to the space.

Cabin in Meaford

Minniehill A-Frame

Designed as a tiny home with everything you need, this semi off-grid cabin is tucked away in Minniehill, Meaford, Ontario. Minutes from beautiful Georgian Bay, down the road from the Bruce Trail hiking entrance, local public and private ski hills, and some of Ontario's best restaurants, while feeling like you've left the rest of the world behind.

Popular amenities for Lion's Head family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 134 reviews

A charming wooden cabin stands surrounded by lush green farm fields. Two light-colored chairs are positioned on the porch, providing a welcoming touch. The cabin features large windows and a unique circular entry, complemented by the vibrant greenery of trees and crops nearby.

Tiny homes in Kimberley

Boho Beaver Cabin 1 with saltwater hot tub

Apartment in Wasaga Beach

The spacious bedroom features a king-sized bed adorned with decorative pillows, complemented by a wooden bedside tray. An armchair occupies one corner, with a desk and paddles adorning the wall. Floor-to-ceiling windows illuminate the room, while exposed wooden accents add a rustic touch.

4.95 out of 5 average rating, 462 reviews

The Upper Deck

Tiny homes in Horning's Mills

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

4.91 out of 5 average rating, 180 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

Cottage in Northern Bruce Peninsula

A peaceful outdoor area is showcased, featuring a hot tub and a cedar barrel sauna set among tall trees. The patio is furnished with stylish black wire chairs, creating an inviting space for relaxation.

4.95 out of 5 average rating, 217 reviews

Glamping Cabin Nature Retreat

4.94 out of 5 average rating, 199 reviews

An inviting outdoor space features a firepit surrounded by several chairs, set against a backdrop of trees. The spacious deck of the modern house is visible with warm lighting illuminating the interior, creating a welcoming atmosphere as evening approaches.

Cabin in Tobermory

Luxury Tobermory Retreat: Modern Home + Hot Tub

4.97 out of 5 average rating, 176 reviews

Home in Wiarton

Kiss & Bond Water View Colpoys Bay 4 -Seasons

4.83 out of 5 average rating, 114 reviews

The cottage exterior features a green wood and stone facade, with large windows and an inviting porch. A spacious deck is furnished with chairs and a table, surrounded by natural greenery. An outdoor umbrella provides shade for relaxation.

Cottage in Tobermory

Custom Built Craftsman Cottage on Lake Huron

4.96 out of 5 average rating, 114 reviews

A welcoming entryway features dark wood paneling and a rustic wooden bench. A framed sign labeled 'Yellow Brick' is displayed prominently on the wall. Decorative plants are placed in woven baskets, adding natural elements to the space.

Home in Mount Forest

The Yellow Brick Guest House

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 157 reviews

A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.

Tiny homes in MONO

Whispering Pines Cabin in Woodland Acres

4.99 out of 5 average rating, 147 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

Guesthouse in Lion's Head

4.9 out of 5 average rating, 291 reviews

Stone Cottage By Georgian Bay

4.98 out of 5 average rating, 112 reviews

A cozy living area features a blue mountain mural accent wall, complemented by a dark sofa and round dining table. Soft lighting from two lamps enhances the inviting space, while blue chairs provide a touch of color. The open layout connects to a kitchen, visible through an archway.

Apartment in Meaford

"Hike" at Hills | Pet-Friendly Escape Near Blue Mt

4.82 out of 5 average rating, 152 reviews

A charming glamping bunkie is set amidst vibrant greenery and blooming flowers. The exterior features a welcoming entrance with steps leading up to a white door, framed by colorful planters. Tall trees provide a natural backdrop, enhancing the tranquil atmosphere.

Tiny homes in Hepworth

Coupland Glamping Bunkie, Hepworth, 3 Acres

4.96 out of 5 average rating, 158 reviews

A charming wood cabin is set in a grassy area, surrounded by tall trees. The front porch features a small table and chairs, with a vibrant pumpkin and seasonal flowers nearby. The cabin has a sloped roof and multiple windows that invite natural light.

Cabin in Port Elgin

Serene and Cozy Cabin

4.92 out of 5 average rating, 212 reviews

An outdoor space features a picnic table with an umbrella, set near a tranquil pond. A stack of firewood is positioned beside a large tree, with a fire pit nearby. Lush greenery surrounds the area, creating a peaceful atmosphere.

Guesthouse in Southgate

Cozy, quiet, clean cabin with wi-fi and fire pit.

4.95 out of 5 average rating, 246 reviews

The exterior of a two-story cottage features a spacious lower deck with seating and stairs leading to the upper level. Large windows allow natural light to fill the interior. Lush greenery surrounds the property, creating a natural landscape.

Home in Tobermory

Lakeside Lounge

Family-friendly home rentals with a pool

Condo in Blue Mountain Resort Area

A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.98 out of 5 average rating, 175 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

4.92 out of 5 average rating, 116 reviews

A swimming pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The sleek water reflects sunlight, creating a serene atmosphere. Lush greenery and trees provide a natural backdrop, while a shed sits nearby, offering additional outdoor storage.

Cottage in Meaford

Woodski Retreat w/Heated Pool on 3+ Private Acres

Condo in Blue Mountain Resort Area

A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.

4.93 out of 5 average rating, 562 reviews

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

4.95 out of 5 average rating, 293 reviews

A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

Cottage in Wasaga Beach

GATED RESORT COTTAGE

Townhouse in Blue Mountain Resort Area

An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.

4.94 out of 5 average rating, 532 reviews

3BR Sierra Scandi Chic - Closest to Village

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

Apartment in Blue Mountain Resort Area

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

4.99 out of 5 average rating, 169 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle