
Family-friendly holiday 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.

RELAX @ our HOT TUB and SAUNA in the woods
PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Saltbox by the Bay/Vetta/4-Season Cottage Escape
Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage is upcycled with luxe amenities. Made for slow living, play boardgames & classic albums, cook up a storm & watching sunsets over the bay. Explore the charms of cottage country: hike or snowshoe the Tay Shore Trail, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, ski/snowboard Moonstone or stop by one of the nearby towns for dinner & bowling.

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.

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.

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.

Hillside Haven: Serene Studio Retreat for 4
Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Cozy Deluxe Studio 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!

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.

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.

Cozy Beach Cottage with Pool | Georgian Bay
Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Cozy getaway for two with hot tub!
Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

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.
Popular amenities for Midland family-friendly rentals
Family-friendly home rentals with a hot tub

Private 40 Acre Cottage with Hot Tub

Glamping Dome Riverview Utopia

Lakefront Cozy Cottage w Hot Tub!

Northern Peaks – Ski In/Out • Hot Tub • Shuttle Ac

Waterfront Paradise on the Georgian Bay

Luxury Guest House with Private Hot Tub and Trails

OakRidge Retreat-HOT TUB 100s of acres WIFI

Serene Comfort. Hot Tub, Full Suite with Kitchen
Family- and pet-friendly home rentals

Whispering Pines Cabin in Woodland Acres

Modern, Private and Luxurious!

The Guesthouse on the North Shore Trail

Mackenzie Cottage

Woodland Muskoka Tiny House

Modern Condo at Friday harbour/Pet Friendly

Cozy Cabin Getaway Muskoka

Ultimate Georgian Bay Vacation Getaway
Family-friendly home rentals with a pool

Lovely 3 Bedroom Condo with Stunning View and Pool

Farmhouse Guest Suite; Year round hot tub

GATED RESORT COTTAGE

3BR Sierra Scandi Chic - Closest to Village

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

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Luxury Beach Spa w/ Private Sauna!
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $214 AUD | $204 AUD | $198 AUD | $222 AUD | $248 AUD | $291 AUD | $345 AUD | $336 AUD | $288 AUD | $256 AUD | $220 AUD | $235 AUD |
| 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 |
Quick stats about holiday rentals that are family-friendly in Midland

Total holiday rentals
Explore 120 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $62 AUD per night before taxes and fees

Verified guest reviews
Over 6,040 verified reviews to help you choose

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
120 of Midland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Midland rentals

4.7 Average rating
Midland stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Rentals with a patio Midland
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- Rentals with a hot tub Midland
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- Rentals with beach access Midland
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- Rentals with pools Midland
- House rentals Midland
- Pet-friendly rentals Midland
- Rentals with a fireplace Midland
- Rentals with a fire pit Midland
- Family-friendly rentals Simcoe County
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- Family-friendly rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- The Club At Bond Head
- Windermere Golf & Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
- Mansfield Ski Club
- Hawk Ridge Golf & Country Club
- Heritage Hills Golf Club
- Springwater Golf Course




