Family-friendly holiday rentals in Penetanguishene

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

4.97 out of 5 average rating, 507 reviews

Apartment in Penetanguishene

The historic Beck House is depicted in this image, showcasing its striking red facade and unique architectural features. A white porch with hanging plants can be seen on the front. The surrounding greenery adds to the charm of the property.

The Haunted House Apt 301

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

4.91 out of 5 average rating, 336 reviews

4.97 out of 5 average rating, 178 reviews

A vibrant garden showcases a variety of colorful flowers, with a prominent rock identified by the number 14. Lush greenery surrounds the area, adding to the inviting outdoor space in front of a brick house. Well-maintained lawns complement the floral displays.

Home in Penetanguishene

White Rolling Sands of Penetang by Theatre

Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

4.97 out of 5 average rating, 133 reviews

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

4.84 out of 5 average rating, 191 reviews

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

Cottage in Waubaushene

Waterfront Paradise on the Georgian Bay

This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle board for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

4.96 out of 5 average rating, 182 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.98 out of 5 average rating, 156 reviews

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

5.0 out of 5 average rating, 290 reviews

A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.

Cabin in Bracebridge

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

4.95 out of 5 average rating, 125 reviews

Villa in Tiny

In Pines •Family-Friendly • Screened Porch • Beach

Escape to In Pines — a bright and spacious retreat nestled in Tiny, LaFontaine, just a 3–4 minute walk to the beautiful sandy beaches of Georgian Bay. Wake up to sunlight streaming through large windows, enjoy peaceful mornings surrounded by nature, and unwind by the fire pit or on the cozy screened porch after a day at the beach. Designed for comfort and connection, this home is perfect for families and groups looking to relax, recharge, and create lasting memories in every season.

4.92 out of 5 average rating, 396 reviews

A cozy bedroom features a wooden headboard with a herringbone pattern and decorative elements. Two bedside tables hold lamps and small plants, while a wall display includes round mirrors and framed signs. Light-colored bedding is complemented by a decorative pillow, creating a welcoming ambiance.

Loft in Midland

Perch by the Bay - Downtown Midland / Private Loft

Welcome to Perch By The Bay, a stylish retreat in downtown Midland. Park for free and walk to Midland Harbour, shops, restaurants, cafe's and waterfront trail. Enjoy festivals, theatre, artisan markets, and great dining nearby. Local sights, include Vetta Nordic Spa, Multicultural Centre, Horseshoe, Moonstone, Saint Marie, King's Wharf & Discovery Harbour. Traveling with others? Our sister Airbnb, Nest By The Bay, is a 2 bedroom private loft at the rear of this building.

A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.

4.97 out of 5 average rating, 116 reviews

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

4.95 out of 5 average rating, 223 reviews

A modern garage apartment is displayed, featuring a neutral-toned exterior with a large garage door and a side entrance. A spacious driveway is visible, providing ample parking space. The entrance is highlighted by a white door, and trees are partially visible in the background.

Apartment in Midland

Hosted by Nous Midland

Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

Popular amenities for Penetanguishene family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The cottage is nestled among tall trees, surrounded by lush greenery and vibrant flowers. Soft lighting from the windows casts a warm glow, emphasizing the inviting atmosphere. Stone pathways and landscaping create a harmonious blend with the natural setting.

4.84 out of 5 average rating, 166 reviews

The Bay View Cottage w/hot tub

4.99 out of 5 average rating, 233 reviews

Townhouse in Port Severn

Pool, Wifi, Free parking, Golf, Laundry, BBQ

4.91 out of 5 average rating, 304 reviews

Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

4.96 out of 5 average rating, 134 reviews

A unique wooden sauna, shaped like a barrel, is placed on a grassy area by the lake. Above, a clear night sky is filled with bright stars, providing a serene backdrop. Nearby, lounge chairs are arranged on the lawn, with trees lining the water’s edge.

Cottage in Coldwater

Cottage on the Rocks - with Hot Tub and Sauna!

4.86 out of 5 average rating, 558 reviews

A charming cottage is seen surrounded by trees, with a large deck above. A fire pit is centrally located in the grassy yard, circled by several wooden chairs. A kayak rests nearby, hinting at outdoor activities, while the serene natural setting offers a peaceful retreat.

Cottage in Waubaushene

Charlie the Cottage | Hot Tub | Trail | Hike/Run

4.78 out of 5 average rating, 116 reviews

A serene waterfront area features a wooden dock with ample seating and a designated space for watercraft. Nearby, kayaks, a paddle boat, and a colorful inflatable banana boat are arranged on the shore, with lush greenery and calm water surrounding the space.

Cottage in Port Carling

Muskoka Luxury Cottage.Hot Tub/Outdoor Steam Sauna

4.96 out of 5 average rating, 208 reviews

Dome in Utopia

Glamping Dome Riverview Utopia

4.94 out of 5 average rating, 303 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 288 reviews

The kitchen features dark wooden cabinetry and a spacious island with seating. A full range of stainless steel appliances are visible, including a refrigerator and stove. Ambient lighting from pendant fixtures enhances the open layout, which combines dining and kitchen areas beneath a vaulted wooden ceiling.

Home in Port Mcnicoll

Spectacular Waterfront 3 Bedroom Home!

A charming beach house features a sloped roof and inviting front porch. Steps lead up to the door, flanked by chairs on either side. Large windows allow natural light into the cottage, while sandy grounds create a seamless connection to the surrounding beach.

4.88 out of 5 average rating, 147 reviews

Cozy beach house on Georgian Bay

4.97 out of 5 average rating, 173 reviews

The exterior of the A-frame home is showcased, featuring a striking black facade and tall triangular roof. Large windows illuminate the interior, and a spacious wooden deck extends across the front, surrounded by lush greenery that encapsulates the natural setting.

Home in Georgian Bay

A-Frame Hidden in the Forest Muskoka, Georgian Bay

Cottage in Penetanguishene

A welcoming outdoor deck features wooden railing and a shaded seating area with a patio umbrella. The deck is surrounded by lush greenery, providing a serene setting. The home’s exterior showcases a blue facade with large windows allowing natural light to enter.

Tiny House in Penetanguishene

4.96 out of 5 average rating, 250 reviews

4.93 out of 5 average rating, 179 reviews

Cottage in Gravenhurst

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

4.99 out of 5 average rating, 105 reviews

A small, wooden bunkie stands among tall trees, featuring a welcoming front porch with two chairs and a table. Decorative elements, including tiki torches and a floral wreath, add charm to the natural setting. The ground is covered with soft pine needles.

Cabin in Oro-Medonte

Bunkie in the Pines

4.95 out of 5 average rating, 506 reviews

An open living area showcases a compact yet functional layout. A spacious sofa is positioned beside a wooden dining table. Two lofts with skylights are seen above, while the kitchen features modern appliances and a contemporary design.

Tiny home in Waubaushene

Unique TinyHome

4.95 out of 5 average rating, 191 reviews

A calm lake setting is depicted, featuring a wooden dock extending into the water. Several ducks swim leisurely near the dock, with lush greenery lining the opposite shore. Fluffy clouds drift across a blue sky, reflecting on the tranquil surface of the water.

Cottage in Gravenhurst

Relaxing lakehouse + pool table & private docks

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 330 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

Condo in Horseshoe Valley

Highland Grand Retreat Studio

4.93 out of 5 average rating, 111 reviews

4.77 out of 5 average rating, 106 reviews

An indoor pool is framed by large windows that allow natural light to fill the space. The ceiling features wooden beams that create an airy atmosphere. Two chairs are positioned nearby, and vibrant yellow flowers are visible through an adjacent window.

Home in Orillia

House ~ Pool ~ Fire Pit ~ BBQ

4.91 out of 5 average rating, 293 reviews

Cottage in Innisfil

Utopia villa and spa

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.

Lovely 3 Bedroom Condo with Stunning View and Pool

4.99 out of 5 average rating, 235 reviews

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.

Blue Vista | Pool/Hot Tub/Shuttle/WalkToBlue

4.94 out of 5 average rating, 659 reviews

Condo in Horseshoe Valley

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

4.99 out of 5 average rating, 137 reviews