Kid-friendly holiday rentals in Midland

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Midland

Guests agree: These kid-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 215 reviews

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...

23 – 30 Apr

$1,439 AUD total

Guest favourite

Apartment in Penetanguishene

4.92 out of 5 average rating, 122 reviews

Church Hill Haven Bed & Breakfast Guest Suite #1

A continental breakfast (a fruit, yogurt & baked good) now available for a small extra cost - please give at least 48 hours if you would like this, (need to know allergies & preferences.) or save money & bring your own & prepare in equipped kitchen. Separate basement walkout entrance with own back deck. (The owner lives on the upper level.) There is a queen size bed in the bedroom & a pull-out queen bed in the LR. The toilet & sink are separate from the walk-in shower. BBQ available in summer.

21 – 28 Sept

$862 AUD total

Guest favourite

Apartment in Penetanguishene

4.88 out of 5 average rating, 379 reviews

The Haunted House Apt 302

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.

8 – 15 Apr

$1,518 AUD total

Guest favourite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 192 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

10 – 17 Nov

$1,834 AUD total

Guest favourite

Home in Penetanguishene

4.97 out of 5 average rating, 143 reviews

White Rolling Sands of Penetang by Theatre

Enjoy a firepit in the private backyard of a large deep lot backing onto woods with trails. Local walking and cycling routes, or stay home and enjoy the veggie and flower gardens from 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 are nearby.

30 May – 6 June

$1,333 AUD total

Guest favourite

Loft in Midland

4.88 out of 5 average rating, 285 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.

6 – 13 Sept

$1,541 AUD total

Guest favourite

Cottage in Port McNicoll

4.98 out of 5 average rating, 125 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

5 – 12 Oct

$1,487 AUD total

Guest favourite

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 229 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

6 – 13 Nov

$2,192 AUD total

Guest favourite

Cottage in Torrance

4.97 out of 5 average rating, 195 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

20 – 25 May

$1,306 AUD total

Guest favourite

Condo in Oro

4.9 out of 5 average rating, 155 reviews

Spacious 1-br w pool & jacuzzi at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

22 – 29 Sept

$1,147 AUD total

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 206 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2024-017

23 Feb – 2 Mar

$2,026 AUD total

Guest favourite

Home in Midland

4.83 out of 5 average rating, 169 reviews

The Little Lake House

The Little Lake House can be described as charming, and cozy. Located close to downtown, and a short walk from Little Lake Park, this newly renovated house is a sweet spot for your next stay in Midland. Relax, and read a book in the little backyard. Go out for a scrumptious meal downtown, or choose to stay in, and cook in our airy & bright kitchen. With 2 cozy bedrooms, you'll feel well rested in one of our pillow-top beds.

1 – 8 Mar

$1,426 AUD total