Family-friendly vacation rentals in Essa

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Essa

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

0 of 0 items showing

1 of 3 pages

Superhost

A sandy beach extends towards clear blue waters, gently lapping at the shore. Smooth stones are visible at the water's edge, while distant land can be seen across the bay. The scene is bright and open, with minimal vegetation along the shoreline.

Cottage in Tiny

4.78 out of 5 average rating, 178 reviews

Lakefront Private Beach, Waterfront Family GBay

Our property is a PRIVATE LAKEFRONT WATERFRONT on Georgian Bay. The beach and swim bay is for your exclusive use! NOT shared with others! Our private bay is part of thousands of square miles of open freshwater, twenty steps across our private lawn is over 100 feet of private sandy shoreline for your family's exclusive use! The PRIVATE BEACH is great for swimming snorkelling and the water is ultra clean and clear! A waterfront property stay means you're at the beach all the time! STRTT-2022-041

Guest favorite

A cozy bedroom features a wooden headboard with a herringbone pattern and decorative elements. Two bedside tables hold lamps and small plants, while a wall display includes round mirrors and framed signs. Light-colored bedding is complemented by a decorative pillow, creating a welcoming ambiance.

Loft in Midland

4.92 out of 5 average rating, 296 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

Top guest favorite

A spacious living area features a comfortable gray sofa and a rustic wooden coffee table. A red tray holds decorative items. The room is brightly lit, with a view of the dining area, which includes a large table surrounded by multiple chairs. Family-themed decor is visible on the walls.

Townhouse in The Blue Mountains

4.96 out of 5 average rating, 328 reviews

Great kitchen, comfy beds, games, walk 2 village +

You will love our fully renovated, condo with quality mattresses, well stocked kitchen, beautiful bathrooms, private ski locker, free parking & the comforts of home. You can trust our 300+ reviews telling stories of amazing getaways & cherished memories made! Our ideal location, only a 5 minute stroll to the village is something you will be sure to enjoy. NETFLIX, cable & unlimited wifi, a cozy gas fireplace, quality towel/ linens + games/duplo...message us re: discounted dates or to book now.

Guest favorite

A modern bathroom features a dual-sink vanity with sleek cabinetry, a large mirror, and stylish wall art. The space is illuminated by recessed lighting, with plush white towels hanging neatly. A toilet and wastebasket are positioned beside a light-colored tiled shower area.

Condo in The Blue Mountains

4.85 out of 5 average rating, 141 reviews

Large, luxury, upper floor condo, steps to Village

Ideally located in exclusive Sierra Lane development, nestled between the Village, Monterra golf course and Blue Mountain ski hill. Perfect for families or non-rowdy girl or guy getaways. This renovated condo includes well appointed kitchen & washrooms, as well as a large open concept living / dining area. Living area includes high end furniture and hardwood floors. Bedrooms have all the comforts of home including upgraded mattresses & high quality bed linens. STA Licence# LCSTR20220000079

Top guest favorite

A spacious backyard is enclosed by tall greenery, providing privacy. A fire pit, surrounded by stones, is positioned on the lush green lawn. A shed is visible to the left, with outdoor equipment stored nearby. Tall trees offer shade and a calm atmosphere.

Bungalow in Wasaga Beach

4.93 out of 5 average rating, 121 reviews

Nice Wasaga Cottage

We welcome well traveled guests over the age of 25 and families. Perfect for 4 people. Large 2 bedroom, 4 season cottage with big living room and eat-in kitchen; in a desirable area of Wasaga Beach Area 4. Renovated kitchen and bathroom. WiFi, gas furnace, and central air conditioning. 1 block to beach area, park, and bike path. 1 block to Nottawasaga river and boat launch. 25 min to Blue Mountain Village. Hiking, Golfing, and Skiing all nearby. 1 extra guest allowed for an additional fee.

Superhost

A warm entrance area is highlighted by wooden paneling and rustic decor. A long bench runs along one wall, and hooks are mounted for hanging gear. The space is well-lit, with a combination of natural light and overhead fixtures creating an inviting welcome.

Cabin in The Blue Mountains

4.87 out of 5 average rating, 361 reviews

"Tequila Sunrise" Big Space-Lots of Fun-HotTub

** Multi night Discounts! **Book for 3 Days or More and get 10% Discount** **Minimum 2 Night Stay** - Hot Tub is PRIVATE NOT shared and available all year - Perfectly equipped for a fun filled stay with a large groups of friends - 15 min walk to the Village at Blue Mountain - Fully stocked kitchen - Natural Gas BBQ ( No need to bring Propane Tanks) - Foosball, ping pong, board games, chalk board, huge kitchen table - - Fire pit is PRIVATE - No kids, No pets, Strictly No Smoking inside.

Guest favorite

The entrance features a white door with a window, leading to a wooden bench and wall paneling. A coat rack and hooks provide storage for jackets, while a black rubber mat enhances the space.

Condo in The Blue Mountains

4.95 out of 5 average rating, 857 reviews

Stunning Mountain Views- WalkTo Blue, Pool, HotTub

SHUTTLE, HOT TUB, SEASONAL POOL! 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ Enhanced Cleaning Protocol ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms Pool open until September 3rd 2024. Hot Tub open all year round!

Superhost

A cluster of charming cottages is arranged along a dirt pathway, framed by trees. Each cottage features light-colored siding and distinct roofs. Lush shrubs are positioned near the entrance of each cottage, contributing to the inviting appearance of the property.

Guesthouse in Wasaga Beach

4.86 out of 5 average rating, 107 reviews

2 -Sun Angel Court Couples Cabin 2

We are a group of ten unique and pretty cottages, located directly In front of Beach 2. We back onto the Nottawasaga River(excellent for fishing). We are extremely clean and have a separate washroom facility for our cottages. There is a common picnic area , overlooking the river with 2 full Bbq's available for guest use. We have a fire pit for late night hotdogs, smores and marshmallow roasting. We are a 5 min walk from the waterfront square- this is where all the special events take place.

Guest favorite

The living area features two cozy sofas arranged around a glass coffee table. A decorative bowl sits atop the table, and vibrant flowers add a touch of color. Large windows invite natural light, showcasing views of the surrounding trees.

Home in Tiny

4.87 out of 5 average rating, 128 reviews

Beachy Blue Bay Cottage - licence #STRTT-2024-195

A 2 min walk to the beach, this 4 bedroom Cottage with Circular Driveway is bright and newly renovated with an open concept main floor. Very private and surrounded by mature trees. Relax on a very large deck with gas BBQ, seating and patio table. Over looking the deck is the fire pit area with lots of room for the kids to play & roast s’mores. The basement is well equipped with pool table, dart board, air-hockey, kids toys, board games & a small TV with lots of movies to snuggle up to!

Superhost

A wooden door stands open, revealing a scenic view of the outdoors. Natural light filters through the glass, illuminating the cozy interior. A comfortable couch and window with shades are visible, creating an inviting entryway.

Chalet in Blue Mountains

4.81 out of 5 average rating, 160 reviews

Escape to Northview Chalet Blue Mountain

"minutes to Blue Mountain Village" - great restaurants, activities, and nightlife. Ask about and late check-out availability!! 10-15 min walk with a view of the hill the entire way - Incredible Views from front Deck, Beach 5min car ride away. Wood Fireplace, Hardwood Floors Great Outdoor sitting Areas, BBQ Private Backyard Area, fire pit. Central Air Conditioning - hot summer nights. Free Wi-Fi Ski, Golf Great for couples, solo adventurers, business travellers, families.

Superhost

The exterior of a multi-level condo building is highlighted, featuring a central chimney and triangular rooflines. Wooden balconies provide outdoor space on both levels, with a sign indicating unit number 7 prominently displayed. Clear blue skies add to the inviting atmosphere.

Townhouse in The Blue Mountains

4.88 out of 5 average rating, 178 reviews

Private condo getaway at base of Blue Mountain

Open loft condo at the base of The Blue Mountains, wifi, air conditioning, parking, self check-in, ski-in/out at north chairlift. Sleeps 4 - 5, with 2 full bathrooms, full kitchen with granite counter tops, fireplace, free parking. Seasonal Outdoor pool and year round shared hot tub. 2 min to beaches and village. Surrounded by nature trails. Walk to ski lift. Fun family or getaway retreat with year round activities. Rental License #LCSTR202200000099

Guest favorite

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. A wooden pathway leads to the water, while a few people are seen walking along the beach, enjoying the serene coastal atmosphere.

Villa in Tiny

4.9 out of 5 average rating, 146 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-2025-152

0 of 0 items showing

What guests are saying

Tiny Home Tranquility

4.91 out of 5 average rating, 1,116 reviews1 week ago

My husband and I booked Tiny Home Tranquillity for our anniversary. Our granddaughter’s dance competition was in Collingwood during our anniversary weekend so we made a spur of the moment booking and were fortunate that Steph’s place was available for the two nights we wanted. It is small, but has everything you need and in its smallness is delightfully uncluttered. The ladder to the loft bedroom could be a bit dicey for older people, but my husband and I are just on the edge of that category and didn’t have any trouble with it at all . We’re thinking of rebooking, depending on availability, and doing a motorcycle tour to Collingwood when the weather is nicer. Tiny Home Tranquillity is definitely a five star Airbnb. Thanks Steph and Jenn!

Guest suite in Collingwood

What guests are saying

Private log cottage on 2 acres

4.68 out of 5 average rating, 225 reviews5 days ago

We recently held our annual family birthday weekend at Natalia's place with a multi-generational crew that spanned 1.5 years to 90 years young! This incredible log cabin met all of our needs. The bedroom on the main floor meant an accessible space for our great aunt, the games room in the basement was such a fun space for our teens. The sliding doors to the wide front porch and the giant yard with fire pit, play structures and trampoline gave us lots of space to play. Plenty of fridge and freezer space and bathrooms on every level was really helpful. Natalia was very responsive and kind as a host. Balm Beach is gorgeous and walkable. There are some really cute restaurants and coffee shops close by (shout out Cawaja General Store and Balm Beach Bar & Smokehouse!) No place is perfect - I note the stairs to the basement are rather steep, and a few suggestions were shared with our awesome host, including about kitchen amenities, but this is a pretty spectacular place to stay for a group.

Home in Tiny

What guests are saying

The Beach House Licence#: STRTT-2024-028

4.96 out of 5 average rating, 72 reviews3 months ago

Place was nice amd cosy for our family break in winter. Great toys collectiom for 2 years old, good books collection for older kids. Only downside was that it didn't have microwave which was tricky with 2 yr old especially when trying to warm up milk quickly. TV could have been bigger fpr the space but it was still good enough. Ian was very helpful and responsove during our stay, he got snow cleaned promptly during our stay.

Cottage in Tiny

What guests are saying

Suites of Wasaga Beach Area 2a

4.75 out of 5 average rating, 12 reviews9 months ago

very well located, and easy to turn over for the bathroom, or have a snack, I would say 2 minutes walk without more. I am not a complicated person. I was happy to have brought a little more stuff, dish soap, hand soap, propane etc. I figured misery the air conditioning, but my friend was successful the next day. the host responds very well and quickly. thank you!

Home in Wasaga Beach

What guests are saying

Designer Condo with beautiful harbour view.

4.93 out of 5 average rating, 206 reviews2 months ago

Staying at Carolyn’s place was an excellent choice! Carolyn was very responsive, communicative and accommodating. The instructions provided were simple and easy to follow. The unit is stunning! You can tell it was designed very well & thoughtful pieces throughout the unit. The unit was really clean. The area had amazing restaurants & shops to check out. I plan to be back during the summer!

Condo in Innisfil

What guests are saying

Great Family Get Away - Wasaga Beach ( 1) wifi

5 out of 5 average rating, 32 reviews7 months ago

I can't begin to describe how wonderful of a host Rocco is. Very kind and accommodating. He instantly feels like family. His place is wonderful- very clean, quiet, convenient (close to the beach and new park), and we just loved staying there. Me and my family will be back here and will definitely recommend it to others.

Home in Wasaga Beach

What guests are saying

Perfect beach vacation getaway, 5 Bedroom

4.83 out of 5 average rating, 80 reviews8 months ago

We had a wonderful stay at Greg’s cottage. He was incredibly accommodating and even allowed us to arrive earlier than planned. The house was spotless, spacious, and packed with indoor and outdoor amenities. The rules and expectations were clearly outlined to ensure a smooth stay. Communication with Greg was excellent throughout our visit. If you're looking for a peaceful beach getaway with clean, sandy shores and uncrowded waters, this is the perfect spot. It's conveniently located just 1.5 hours from Toronto. During our trip, we enjoyed activities such as walking along Barrie Lakeshore, go-karting, playing softball in the Wasaga Beach area, and visiting the Martyr's Shrine. We had an amazing time and highly recommend this place!"

Cottage in Tiny

What guests are saying

Sweet Memories of Georgian Bay

4.9 out of 5 average rating, 50 reviews7 months ago

Idyllic gem on Georgian bay. Perfect for a small family getaway by the lake. The resort pool is a big plus for the kids. Beautiful surroundings and stunning sunsets. Jefferson is a great host. Very friendly and responsive. He kindly accommodated our request.

Bungalow in Lafontaine Beach

What guests are saying

B & B Home Away from Home

4.88 out of 5 average rating, 123 reviews7 months ago

Our stay was absolutely fantastic! We had an amazing time. Dimi was a very reachable and responsive host. His place is extremely spacious and only a 1 minute walk from the beach as well as a 5 minute drive from the main strip. It was very clean and super well equipped with any and everything we needed for our family’s stay. Dimi went above and beyond to accommodate our group. 10/10 stay, definitely recommend! Thank you so much Dimi!!

Bungalow in Wasaga Beach