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Family-friendly vacation rentals in Midland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Midland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An inviting outdoor space features a cozy fire pit surrounded by gravel and wooden seating. Soft lighting from above highlights the stone wall and enhances the serene atmosphere. The area provides a perfect spot for relaxation and outdoor gatherings.

Barn in Eugenia

4.98 out of 5 average rating, 186 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q beds. Main bunky bed, 1 bedroom (please inform if second bed is needed) A relaxing, peaceful farm stay on a working farm with or without your horses. Bright clean bunky built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with the horses.We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, mountain biking.

A wooden dock extends into calm water, featuring Adirondack chairs positioned for relaxation. Sunlight reflects off the water's surface, creating a serene atmosphere. Nearby, a small boat awaits at the bottom of the dock, framed by trees on the opposite shore.

Cottage in MacTier

4.91 out of 5 average rating, 113 reviews

Baysong Cottage, Hot Tub and Sauna on Georgian Bay

*Winter All Wheel Drive and Winter Tires Required* Welcome to Baysong Cottage. We are right on the water, with a big dock, sauna and hot tub all yours to enjoy. This is the perfect getaway winter and summer. Enjoy our dock for swimming and boating, our sauna and hot tub for a rejuvenating spa experience, and all day south west facing sunshine. Great for boating, fishing, sailing, swimming, snowmobiling, ice fishing or just a getaway to enjoy a campfire, some board games and some time together.

Top guest favorite

A spacious living room features a cozy seating area with a dark brown sofa and a comfortable armchair. Natural light floods in through large windows, illuminating a rustic wooden coffee table. A television is mounted on the wall, accompanied by decorative wall art.

Bungalow in Wasaga Beach

4.93 out of 5 average rating, 128 reviews

Nice Wasaga Cottage

We welcome well traveled guests over the age of 25 and families. Perfect for 4 people. Large 2 bedroom, 4 season cottage with big living room and eat-in kitchen; in a desirable area of Wasaga Beach Area 4. Renovated kitchen and bathroom. WiFi, gas furnace, and central air conditioning. 1 block to beach area, park, and bike path. 1 block to Nottawasaga river and boat launch. 25 min to Blue Mountain Village. Hiking, Golfing, and Skiing all nearby. 1 extra guest allowed for an additional fee.

The master bedroom features a spacious bed with a decorative 'RELAX' pillow. Natural light fills the room through a window adorned with dark curtains. Wall art depicting serene landscapes complements the calming neutral tones, while a stylish lamp and small seating area add functional decor.

Loft in Midland

4.89 out of 5 average rating, 352 reviews

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

Top guest favorite

The exterior of a custom-built log cabin is framed by trees under a clear blue sky. A spacious porch features two Adirondack chairs and a fire pit, providing a welcoming outdoor space. Natural stone accents enhance the cabin's rustic charm.

Chalet in Gravenhurst

4.94 out of 5 average rating, 239 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

A serene lake under a bright blue sky is depicted, with reflections of fluffy clouds and surrounding trees mirrored on the water's surface. The peaceful landscape suggests a tranquil environment, populated by various wildlife and foliage along the shoreline.

Cottage in Port Severn

4.88 out of 5 average rating, 138 reviews

2 BEDRM WATERFRONT COTTAGE, CANOE, KAYAKS, WIFI

No linens provided (No Blankets, sheets pillowcases or towels). Sorry NO PETS as guests on the property and NO SMOKING indoors. The cottage is right on the water, lots of wildlife, great for bird watching, Large 4 lake system, miles of boating on Gloucester pool, then for a further adventure it is connected to Georgian bay by locks on the Trent Severn. Honey Harbor, Midland, Whites Falls and lots of provincial parks close by, great fishing, ATV and hiking trails, fish right off the dock

A spacious wooden dock extends over the calm waters of Lake Couchiching, featuring two white Muskoka chairs positioned for relaxing views. The serene landscape includes small islands visible in the distance under a bright blue sky with scattered clouds.

Cottage in Washago

4.79 out of 5 average rating, 258 reviews

The Islandview

Welcome to The Islandview! Located on the sandy shores of Lake Couchiching, this gorgeous 4 season, 2-story open concept cottage is the perfect getaway. Escape to the private sun filled deck or dock on the water. Entertain in the open concept kitchen, two large living areas, or outdoors around the fire. During the day, enjoy watching the kids swim on the beach and at night take in the breathtaking sunsets. 5min to Washago & 10min to Casino Rama. Fully equipped with everything you need!

A spacious outdoor area is highlighted by a stone fire pit, surrounded by two green adirondack chairs. In the background, a cottage with a sunroom and wooden deck is visible, set against a backdrop of lush trees and open grass.

Cabin in Severn Bridge

4.7 out of 5 average rating, 158 reviews

Moon River Place Unit 4B

A modest riverfront cottage with a full kitchen and bathroom. 1 bedroom with a queen bed, a low ceiling loft accessible by ladder with 2 single beds or a futon in the living room, sleeps 4 in total. 20 mins from Orillia, and 15 mins from Gravenhurst. Situated on a lively canal connecting Sparrow lake and lake Couchiching with private access. Perfect for families or small groups looking enjoy some time away from the noise of the city. Please read the listing details carefully!

Top guest favorite

A two-story wooden cottage is surrounded by vibrant autumn foliage, with large windows and a balcony overlooking the landscape. A gravel driveway leads to the entrance, and an attached garage is visible on the right. The natural setting enhances the home's rustic charm.

Chalet in Coldwater

4.95 out of 5 average rating, 470 reviews

OakRidge Retreat-HOT TUB 100s of acres WIFI

The cottage provides a serene space to share with fiends and family surrounded by nature. Enjoy beaver ponds along the trails, indoor/outdoor games, wood burning stove, sauna, hot tub, firepit, wifi, jetted tub 75" & 55" smart tv's and streaming services. Fully equipped kitchen, double oven, granite counter. In winter, snowshoes and snow saucers. At Christmas the house is decorated and boasts a 15 ft tree. 20-25 minutes from Mount St. Louis ski hill and several beaches.

A grassy area is bordered by tall trees, offering a view of the lake. A picnic table sits on the lawn, alongside a lounge chair, with the shimmering water in the background under a clear sky.

Cottage in Innisfil

4.83 out of 5 average rating, 229 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. A wooden pathway leads to the water, while a few people are seen walking along the beach, enjoying the serene coastal atmosphere.

4.9 out of 5 average rating, 150 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2025-152

The exterior of the house displays a classic English-style architectural design, featuring a combination of dark wooden shingles and white stone. Lush greenery surrounds the entrance, complemented by well-maintained hedges and a manicured lawn, enhancing the inviting landscape.

Guest suite in Midland

4.89 out of 5 average rating, 184 reviews

The Carriage Unit: 2 connecting rooms, 1 bathroom

The old Carriage Airbnb is not a 5 stars hotel, but it can be a cozy and comfortable “home away from home” for travellers, workers, students, etc at a reasonable price. “Wake up with determination, go to bed with satisfaction.” At the Carriage Guest unit you will get a good night's sleep and a room service proper breakfast in the morning that will be ready from 7:45 am to 10:00 am. ( no special diet like gluten-free etc.)

Vacation rentals for every style

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Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Midland family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An inviting living area displays high ceilings with wooden paneling. Comfortable seating arrangements are oriented around a central coffee table. A modern fireplace is situated against a feature wall, and large windows allow natural light to fill the space, enhancing the atmosphere.

Chalet in Blue Mountain Resort Area

4.8 out of 5 average rating, 195 reviews

Chalet At Blue - Private chalet with hot tub

A spacious backyard is depicted, featuring a striped hammock supported by a sturdy frame. Lush green grass covers the ground, surrounded by tall trees creating a natural, serene setting. The scene conveys an inviting space for relaxation and outdoor enjoyment.

Bungalow in Innisfil

4.82 out of 5 average rating, 281 reviews

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike

Four white Adirondack chairs are positioned on a pebble beach, facing a calm lake. A wooden dock extends into the water under a bright blue sky, while the sun reflects off the surface, creating a serene atmosphere.

Cottage in Orillia

4.86 out of 5 average rating, 22 reviews

Family cottage just steps away from Lake Simcoe

A wood-paneled hallway features a staircase leading to upper levels, with textured flooring throughout. The walls are adorned with various signs, and multiple doors access nearby rooms. A coat rack is mounted on the wall, contributing to a functional, rustic atmosphere.

Cabin in Blue Mountain Resort Area

4.89 out of 5 average rating, 364 reviews

🍺"Margaritaville" Big Space, Lots of fun+Hot Tub

The exterior of a multi-level condo building is highlighted, featuring a central chimney and triangular rooflines. Wooden balconies provide outdoor space on both levels, with a sign indicating unit number 7 prominently displayed. Clear blue skies add to the inviting atmosphere.

Townhouse in Blue Mountain Resort Area

4.88 out of 5 average rating, 185 reviews

Private condo getaway at base of Blue Mountain

The scene captures a tranquil lake at sunset, with soft clouds reflecting on the calm surface. Lush trees line the shore, and a small dock is visible in the foreground, adding depth to the serene landscape.

Cottage in Port Severn

4.94 out of 5 average rating, 138 reviews

Muskoka Cottage on warm lake - 4 BR/2 BR/Hottub

A modern chalet with a multi-level facade is set amidst trees and shrubbery. The entrance features a large, bright door flanked by windows. A porch with a shaded seating area is visible, surrounded by well-maintained landscaping and stone accents.

Chalet in Blue Mountain Resort Area

4.98 out of 5 average rating, 110 reviews

Walk to the village at Blue - Regal

A spacious dining area features a large wooden table with bench seating under an arched ceiling. Large windows allow for natural light, highlighting the rustic stone accents and wooden beams. A cozy seating area is visible in the background, enhancing the inviting feel of the space.

Chalet in Blue Mountain Resort Area

4.89 out of 5 average rating, 109 reviews

Rustic Spanish Chalet inthe Heart of Nature/hottub

Family- and pet-friendly home rentals

Top guest favorite

Two wooden adirondack chairs are positioned on a sunlit wooden dock, facing a calm lake. The water reflects the surrounding trees and sky, creating a serene atmosphere for relaxation and enjoyment.

Cottage in Gravenhurst

4.97 out of 5 average rating, 63 reviews

Stunning Log Cottage on an Island in Muskoka

A wooden dock extends over tranquil waters, featuring six turquoise Muskoka chairs arranged to face the serene landscape. Tall trees line the riverbank, providing a natural backdrop under clear skies.

Cottage in Washago

4.93 out of 5 average rating, 55 reviews

Stunning Waterfront w/Hot Tub - Nature's Cottage

A sun sets gently over a calm lake, casting warm colors across the sky. Two red loungers are positioned on sandy beach, offering a serene spot for relaxation. Verdant greenery borders the shoreline, creating a peaceful natural backdrop.

Cottage in Penetanguishene

4.83 out of 5 average rating, 29 reviews

3 Bdrm Family Cottage Private Beach, Thunder Beach

A uniquely shaped chalet is framed by a snowy landscape, featuring a spacious wooden deck that wraps around the front. Large windows allow natural light to fill the interior, while a clear blue sky complements the winter scenery.

Chalet in Blue Mountain Resort Area

4.83 out of 5 average rating, 171 reviews

Octagon Chalet fire pit, close to theVillage

The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.

4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

The cottage is situated on a granite rock, surrounded by trees and natural vegetation. A wraparound deck extends partially around the dwelling, with steps leading to the entrance. The structure features large windows, allowing for natural light to fill the interior.

Home in Coldwater

4.68 out of 5 average rating, 85 reviews

Muskoka Cottage on the Severn River

A classic cottage is situated along the Severn River, surrounded by greenery. A small dock extends into the water, with a canoe nearby. A few chairs are arranged on the lawn, providing a relaxing spot to enjoy the riverside views. The cottage features a welcoming porch adorned with comfortable seating.

Cottage in Severn Bridge

4.7 out of 5 average rating, 91 reviews

Waterfront Muskoka Cottage on Trent-Severn River

A tranquil lakeside scene features a wooden dock extending into a still body of water, reflecting the surrounding mist and greenery. Two red chairs are positioned on the dock, accompanied by a small canoe tied at the edge, creating a serene atmosphere.

Cabin in Port Severn

4.66 out of 5 average rating, 108 reviews

Firedragon B/ Six Mile Lake / Port Severn/Muskoka

Family-friendly home rentals with a pool

An outdoor pool area is surrounded by a wooden deck, featuring several patio tables with umbrellas. The clear blue pool invites relaxation, while trees and greenery provide a natural backdrop. The building's architectural style includes blue accents and large windows, enhancing the overall aesthetic.

Chalet in Blue Mountain Resort Area

4.83 out of 5 average rating, 794 reviews

Blue Mountain / Collingwood Hill Side Condo

Townhouse in Blue Mountain Resort Area

4.9 out of 5 average rating, 157 reviews

The Snowbridge Lookout on Monterra Golf Course

Townhouse in Blue Mountain Resort Area

4.96 out of 5 average rating, 106 reviews

Luxury Vacation Home at Blue Mountain Village

Townhouse in Blue Mountain Resort Area

4.94 out of 5 average rating, 512 reviews

3BR Sierra Scandi Chic - Closest to Village

An outdoor swimming pool is surrounded by lush greenery and tall trees. The pool features a gentle curve design, with clear blue water and a shallow entry area. Several white lounge chairs are positioned around the pool, inviting relaxation in a peaceful setting.

Condo in Blue Mountain Resort Area

4.85 out of 5 average rating, 144 reviews

Large, luxury, upper floor condo, steps to Village

Condo in Blue Mountain Resort Area

4.95 out of 5 average rating, 884 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

Top guest favorite

A clear, inviting outdoor pool is surrounded by landscaped greenery and stone seating areas. The pool features a curved shape with steps leading in, and two poolside lounge chairs are visible. Mature trees provide shade in the background, enhancing the serene environment.

Townhouse in Blue Mountain Resort Area

4.96 out of 5 average rating, 332 reviews

Great kitchen, comfy beds, games, walk 2 village +

A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.

Condo in Blue Mountain Resort Area

4.92 out of 5 average rating, 348 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Quick stats about vacation rentals that are family-friendly in Midland

Total rentals
130 properties
Nightly prices starting at
R709 ZAR before taxes and fees
Total number of reviews
5.7K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace

Destinations to explore