
Family-friendly holiday rentals in Midland
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Midland

Total holiday rentals
Explore 110 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 5,760 verified reviews to help you choose

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
100 of Midland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Midland rentals

4.8 Average rating
Midland stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated family-friendly rentals in Midland
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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...

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.

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.

Loft By The Bay
Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

Off-grid Glamping Dome Nestled in the Woods
Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

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.

The Bubble Glamping Dome
Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

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

Modern Waterfront Home on Georgian Bay w/ Hot Tub!
Escape to a peaceful haven with this new and breathtaking modern waterfront cottage. Immerse yourself in the stunning views from the walkout deck with outdoor seating, a hot tub and a BBQ area. Quiet neighbourhood in Victoria Harbour on Georgian Bay. Short drive to charming town of Midland and nearby attractions such as the Tay Shore Trail and the Wye Marsh Wildlife Centre. This bright and beautifully finished home is less than a 2-hour drive from the GTA.

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.

House on the Hill, HotTub, Relaxation, Bike Trails
Experience the perfect blend of historic charm and modern comfort in this century home. Bask in the refreshing breeze from Georgian Bay and enjoy the tranquility it brings. Explore nearby downtown shops, take advantage of the Trans Canada Trail for walking, running or biking, and discover a variety of local attractions just minutes away.

Unique TinyHome
This is a unique space with great attention placed on details. I design and build unique livable spaces catered to the individual needs of my clients. I invite you to come experience high quality living in a modern tiny home and experience sustainable, affordable living in just 286 square ft.
Popular amenities for Midland family-friendly rentals
Family-friendly home rentals with a hot tub

D O C K | NEW Modern Muskoka Waterfront 2+1 bed

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

Glamping Dome Riverview Utopia

Lakefront Cozy Cottage w Hot Tub!

Georgian Bay Cottage-HotTub/Sauna/Swim/Hike/Marina

Cottage on the Rocks - with Hot Tub and Sauna!

Waterfront Paradise on the Georgian Bay

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom
Family- and pet-friendly home rentals

Serenity, Simplicity and Stone

The Cottage on Coldwater; where bay & trail meet.

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Cozy Cabin Getaway Muskoka

Teremok Cabin at Zukaland | Cedar Hot Tub & Sauna

Log Cabin on the Lake Bed and Breakfast

In Pines •Cozy Escape • Screened Porch • Beach

Cozy beach house on Georgian Bay
Family-friendly home rentals with a pool

GATED RESORT COTTAGE

King Bed, Pool, Gym, Ravine View, Your Getaway!

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Utopia villa and spa

Ski, Swim, Soak, Boat & Golf

Resort Condo (2 suites) near Horseshoe Valley

King’s Escape at Blue Mountain
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 SGD | $204 SGD | $186 SGD | $183 SGD | $204 SGD | $240 SGD | $285 SGD | $277 SGD | $238 SGD | $227 SGD | $181 SGD | $208 SGD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
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- Rentals with a patio Midland
- Rentals with an EV charger Midland
- Flat rentals Midland
- Beachfront rentals Midland
- Rentals with lake access Midland
- Cottage rentals Midland
- Rentals with beach access Midland
- Rentals with a washing machine and dryer Midland
- Rentals with a fireplace Midland
- Rentals with a firepit Midland
- Cabin rentals Midland
- Rentals with outdoor seating Midland
- Rentals with pools Midland
- Rentals with a hot tub Midland
- Fitness-friendly rentals Midland
- Pet-friendly rentals Midland
- Rentals with a kayak Midland
- Waterfront rentals Midland
- House rentals Midland
- Family-friendly rentals Simcoe County
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Three Mile Lake
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Torrance Barrens Dark Sky Conservation Area
- Taboo Muskoka Resort & Golf
- Kee To Bala
- Burl's Creek Event Grounds
- Casino Rama Resort
- Menominee Lake
- Awenda Provincial Park
- Wasaga Beach Area
- Wye Marsh Wildlife Centre
- Mono Cliffs Provincial Park
- Bass Lake Provincial Park
- Sunset Point Park
- Innisfil Beach Park
- Killbear Provincial Park
- Centennial Beach





