Family-friendly vacation rentals in Penetanguishene

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Penetanguishene

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Loft in Midland

4.92 out of 5 average rating, 244 reviews

Perch by the Bay - Downtown Midland / Private Loft

Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

Jun 17 – 24

ﺩ.ﺇ576 per night

Guest favorite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q. beds A relaxing farm stay on a working farm with or without your horses. Bright clean bunkie built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with your horses in the morning. We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, atving, mountain biking. Check out the beautiful sunset behind the barn.

Oct 29 – Nov 5

ﺩ.ﺇ629 per night

Guest favorite

Home in Penetanguishene

4.98 out of 5 average rating, 150 reviews

Lafontaine Beach Paradise

Welcome to our Retreat in Paradise! A place where your body, mind and soul will relax! This stately executive home offers an elegant appeal inside and out, with 4000 sf of living space boasting an impressive interior with high-end finishes. Perfectly located close to the beach, trails and all amenities. Large windows and surrounded by mature trees on a beautiful quiet street. This home is ready for you to enjoy your get away. Time to start building your loving family memories! READ HOUSE RULES!

Dec 20 – 27

ﺩ.ﺇ1,702 per night

Guest favorite

Apartment in Wasaga Beach

4.95 out of 5 average rating, 356 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

Jan 5 – 12

ﺩ.ﺇ517 per night

Guest favorite

Guest suite in Collingwood

4.92 out of 5 average rating, 1008 reviews

Tiny Home Tranquility

Tiny Home Tranquility! Located just 15 minutes from Blue Mountain Ski Resort and Wasaga Beach. Walking distance to Collingwood downtown core and Georgian Bay . A custom built tiny home with all the amenities needed for a perfect getaway. This clean, bright and cozy tiny home is private and is attached to the main house with a breezeway to comply with the town bylaws. The Tiny Home has a separate entrance and private back patio giving guests total privacy. Absolutely no pets due to allergies.

Dec 21 – 28

ﺩ.ﺇ460 per night

Guest favorite

Cabin in Bala

4.93 out of 5 average rating, 169 reviews

Cabin Medora Lake, Bala

Our place is close to Bala and Port Carling. You’ll love it! It's a big, one room, family cabin on a 6 acre forested property with a 40 sec. walk to our 1100 ft of shoreline on pristine Medora lake, with dock, canoe, great swimming and fishing. This place is good for couples or a family (with kids). A true Muskoka experience. The friendly and quiet owners who live next door have loved this incredible private property for 30 years and will ensure you have all the comforts you need.

Mar 10 – 17

ﺩ.ﺇ719 per night

Guest favorite

Cottage in Bracebridge

4.9 out of 5 average rating, 438 reviews

Cottage on the Muskoka River

The cottage has a nice private setting as part of a parcel of land which is almost 20 acres along the Muskoka River, close to 3 waterfalls and on the Trans Canada Trail. You’ll love our place because of the access to many trails for hiking, yet only a few minutes to downtown Bracebridge and central to most Muskoka Attractions. To really enjoy the river location you need to love walking and exploring. The cottage is offered in its pre-renovation state as the pictures indicate.

Jan 1 – 8

ﺩ.ﺇ508 per night

Guest favorite

Chalet in Coldwater

4.95 out of 5 average rating, 392 reviews

OakRidge Retreat-HOT TUB 100s of acres WIFI HST in

The cottage provides a serene space to share with fiends and family surrounded by nature. Enjoy beaver ponds along the trails, indoor/outdoor games, wood burning stove, sauna, hot tub, firepit, wifi, jetted tub 75" & 55" smart tv's and streaming services. Fully equipped kitchen, double oven, granite counter. In winter, snowshoes and snow saucers. At Christmas the house is decorated and boasts a 15 ft tree. 20 minutes from Mount St. Louis ski hill and several beaches.

Feb 16 – 23

ﺩ.ﺇ1,303 per night

Guest favorite

Apartment in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

Oct 11 – 18

ﺩ.ﺇ284 per night

Guest favorite

Villa in Tiny

4.89 out of 5 average rating, 130 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2022-207

Sep 16 – 23

ﺩ.ﺇ1,781 per night

Guest favorite

Townhouse in The Blue Mountains

4.94 out of 5 average rating, 443 reviews

Sierra Lane - Closest to Village - Fully Equipped

Treat yourself to a getaway at our clean, modern, spacious, and fully-equipped end-unit 2nd & 3rd floor townhouse at 110 Fairway Court. Just a 3 minute walk from the village and facing the Monterra golf course 1st hole, you’ll enjoy beautiful views of the mountain and easy access to village activities. With 1,800 square feet of living space and all the comforts of home, our place has everything you need for a relaxing stay.

May 10 – 17

ﺩ.ﺇ512 per night

Superhost

Cottage in Lafontaine

4.8 out of 5 average rating, 196 reviews

Beach house (with pool open May-Oct)

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! Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! NEW FOR 2024 - renovated bathroom. Note: Pool is closed for the season October 19th.

Oct 16 – 23

ﺩ.ﺇ936 per night