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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Guest favorite

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.

Apartment in Penetanguishene

4.9 out of 5 average rating, 279 reviews

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.

Guest favorite

A modern kitchen features natural wood cabinetry and a large marble countertop island with seating. Stainless steel appliances, including an electric stove and refrigerator, are visible. The space is well-lit with recessed lighting, and decorative plants add a touch of warmth.

Apartment in Midland

4.9 out of 5 average rating, 113 reviews

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.

Guest favorite

A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.

Cottage in Victoria Harbour

4.82 out of 5 average rating, 211 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Guest favorite

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.

Cottage in Tiny

4.98 out of 5 average rating, 128 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.

Guest favorite

The inviting interior features wooden walls with large windows allowing natural light to illuminate the space. A compact kitchenette is visible with appliances, while stylish stools complement a natural wood countertop. A cozy seating area with a futon sits adjacent to a wooden staircase leading to the loft.

Guesthouse in Shanty Bay

4.86 out of 5 average rating, 113 reviews

New Charming tinyhome Experience

Come spend a few days in our warm and cozy hideaway. Enjoy the winter wonderland with some Snow shoeing, cross country skiing or Snowmobiling right from your backyard! OR, perhaps you would like to go to the new Vetta Spa only mins away. Or downhill, snowboard at Horseshoe or Moonstone? OR maybe you just want to disconnect from technology for awhile and reconnect with yourself or loved one. Please inquire if you would like more than 3 guests. The options are plentiful from this location.

Guest favorite

A serene sunset is captured over Georgian Bay, with warm orange and gold hues reflecting on the water. Silhouetted figures are seated on a dock, gazing out towards the horizon, creating a sense of tranquil evening ambiance.

Home in Victoria Harbour

4.84 out of 5 average rating, 149 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Top guest favorite

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

4.95 out of 5 average rating, 148 reviews

Chez 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.

Superhost

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

4.88 out of 5 average rating, 373 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. Listing not suitable for ages under 6.

Guest favorite

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 breakfast in the morning that will be ready from 7:45 am to 10:00 am. ( no special diet like gluten-free etc.)

Top guest favorite

A cozy wooden bunkie is nestled among the trees, featuring a small porch with two bright blue Adirondack chairs. The cabin is constructed with natural wood and has a glass door, allowing glimpses of the serene forest surrounding it.

Tiny home in Orillia

4.94 out of 5 average rating, 100 reviews

Cozy Off-Grid Bunkie on a Horse Farm

Take time away to rejuvenate in nature in our cozy off-grid bunkie on our 25 acre property and horse farm. Our hidden slice of heaven is on outskirts of Orillia, 10 minutes from restaurants, shopping, outings and adventures! Ask us about our Horse Connection experience! Walk our trails, relax with a book, play outdoor games, head to the local beach or enjoy a campfire under the stars.

Guest favorite

A modern tiny home is surrounded by tall trees, showcasing a unique architectural design with a slanted roof. A wooden deck leads to double glass doors that open to the outdoors. A gravel pathway and stone fire pit complement the lush greenery.

Tiny home in Waubaushene

4.95 out of 5 average rating, 414 reviews

Unique Tiny Home

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 280 square ft.

Superhost

A contemporary living area is highlighted by a vibrant red sectional sofa and a glass coffee table. Framed art is displayed on the walls alongside gold record plaques. A stylish floor lamp stands beside the seating, contributing to the modern ambiance.

Apartment in Midland

4.83 out of 5 average rating, 223 reviews

Downtown Midland Diamond Mine

The Diamond Mine is located in the heart of downtown Midland near Georgian Bay! Clean and safe neighbourhood. Steps away to great restaurants and cafes, and only a 10 minute drive to the rich blue waters of Balm Beach. This apartment is a rare find. Experience Midland living at its best!