
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.

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.

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.

Saltbox by the Bay + Snowshoes/Ski/Snowboard/Vetta
DECEMBER AVAILS + Snowshoes + Skiing 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 & watch sunsets over the bay. Explore winter in cottage country: borrow our snowshoes for a trek, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, ski/snowboard Mount St. Louis or head into town for dinner & bowling.

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.

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!

By The Bay spacious one bedroom
This unique place has a style all its own and only steps away from , beaches , water front dining and theater! With all the amenities of home you'll be comfortable to stay for the weekend or extended stays. Fully equipped kitchen with convection oven , dishwasher , microwave, keurig coffee maker and built in washer/ dryer . Spacious bathroom with an over sized walk in shower . And to end the day enjoy the full sized bed room and closet to unpack luggage with a queen size Endy foam mattress .

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.

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!

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.

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

Private 40 Acre Cottage with Hot Tub

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

Glamping Dome Riverview Utopia

Lakefront Cozy Cottage w Hot Tub!

Waterfront Paradise on the Georgian Bay

Luxury Guest House with Private Hot Tub and Trails

Lafontaine Beach Rustic Chalet- New HOT TUB.

Luxury Beach Spa w/ Private Sauna!
Family- and pet-friendly home rentals

A-Frame in the Woods of GeorgianBay, Muskoka

Cozy 4 Season Family Cottage

HOME ON BAY

The Cottage on Coldwater; where bay & trail meet.

The Guesthouse on the North Shore Trail

Woodland Muskoka Tiny House

Log Cabin on the Lake Bed and Breakfast

Orillia TwnHse Oasis w King Bed
Family-friendly home rentals with a pool

Farmhouse GUEST SUITE; Year round hot tub

Après Blue- 2bed2bath w/Pool 6 min walk to village

GATED RESORT COTTAGE

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

Fox Ridge - Ski-In-Out, Hot Tub & Shuttle

Ski in/out @ North Creek W King bed! New Hot Tub

Friday Harbour Luxury Condo Escape, Sleeps 4
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ507 | ﺩ.ﺇ485 | ﺩ.ﺇ470 | ﺩ.ﺇ525 | ﺩ.ﺇ588 | ﺩ.ﺇ690 | ﺩ.ﺇ819 | ﺩ.ﺇ797 | ﺩ.ﺇ683 | ﺩ.ﺇ606 | ﺩ.ﺇ521 | ﺩ.ﺇ558 |
| 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 vacation rentals that are family-friendly in Midland

Total vacation rentals
Explore 120 vacation rentals in Midland

Nightly prices starting at
Midland vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
120 of Midland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Pittsburgh Vacation rentals
- Erie Canal Vacation rentals
- Laurentides Vacation rentals
- Detroit Vacation rentals
- Mont-Tremblant Vacation rentals
- Rentals with a fireplace Midland
- Pet-friendly rentals Midland
- Rentals with lake access Midland
- Cabin rentals Midland
- Rentals with pools Midland
- Rentals with a washer and dryer Midland
- Rentals with a patio Midland
- Rentals with beach access Midland
- Cottage rentals Midland
- Rentals with a kayak Midland
- Rentals with a fire pit Midland
- House rentals Midland
- Waterfront rentals Midland
- Beachfront rentals Midland
- Apartment rentals Midland
- Fitness-friendly rentals Midland
- Rentals with an EV charger Midland
- Rentals with outdoor seating Midland
- Rentals with a hot tub Midland
- Family-friendly rentals Simcoe County
- Family-friendly rentals Ontario
- Family-friendly rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Windermere Golf & Country Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- The Club At Bond Head
- Muskoka Bay Resort
- Lake Joseph Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Mansfield Ski Club
- Alpine Ski Club
- Toronto Ski Club
- Hawk Ridge Golf & Country Club
- Horseshoe Adventure Park
- Springwater Golf Course




