Family-friendly vacation rentals in Essa

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Essa

  • Total vacation rentals

    Explore 60 vacation rentals in Essa

  • Nightly prices starting at

    Essa vacation rentals start at G$6,272 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,360 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Essa vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Essa rentals

  • 4.8 Average rating

    Essa stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Essa

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

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Superhost
The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.
Home in Barrie

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

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

KitchenFamilyPool

4.9 out of 5 average rating, 145 reviews
Top guest favorite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Indoor spacesKitchenSolo travel

4.97 out of 5 average rating, 503 reviews
Top guest favorite
Apartment in Barrie

Spacious very clean, Entire Private Guest Suite

Come and enjoy our private, spacious, and bright 1 bedroom guest suite located in the West Barrie. Enjoy the private entrance and the entire basement unit. Walking distance to Ardagh Bluffs, trails, and bus stop. 10 min drive to HWY 400, shopping areas, and Lake Simcoe. 15 min drive to Snow Valley Ski Resort. - Free parking spot - Free 200 mbps Wifi - Private entrance Kitchenette, Fridge/Freezer, Stove/Oven, Microwave, Toaster, Dishwasher, Laundry, Flat iron, closets - No Smoking - No Pet

FamilyIndoor spacesHospitality

4.95 out of 5 average rating, 130 reviews
Guest favorite
A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.
Tiny home in Mono

Whispering Pines Cabin in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking to relax. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker a mini fridge with freezer and air conditioning. Pursue your favourite outdoor activities during the day and then return to your cozy queen bed and sofa bed just steps away from the bonfire.

KitchenIndoor spacesWifi

4.91 out of 5 average rating, 175 reviews
Guest favorite
A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.
Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 106 reviews
Guest favorite
A geodesic dome is nestled among vibrant fall foliage, showcasing a combination of green coniferous trees and orange and yellow deciduous leaves. The transparent windows of the dome reveal a glimpse of the interior, enhancing the connection to the surrounding nature.
Dome in Utopia

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 292 reviews
Guest favorite
Home in Barrie

Modern 5-bedroom house close to Ardagh Bluffs

Enjoy this new, modern and spacious house with open concept living room, dining room, 5 bedrooms and stylish kitchen with brand new modern appliances. Get together with your family and friends around the indoor gas fireplace watching your favorite movie. Relax in the spa like bathroom, and enjoy your sleep in the comfortable bedrooms .Go for a walk in the nearby forest at Ardagh Bluffs or take a short drive to the shopping centre or picturesque lakefront park. You will enjoy your stay in full!

FamilyIndoor spacesHospitality

4.95 out of 5 average rating, 183 reviews
Top guest favorite
An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.
Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

KitchenFamilyCleanliness

4.95 out of 5 average rating, 167 reviews
Top guest favorite
Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

KitchenFamilyTV

4.91 out of 5 average rating, 304 reviews
Guest favorite
Home in Barrie

Spacious Barrie Basement with Separate Entrance

This 2-bedroom basement unit is bright and spacious, it offers a kitchenette, a bathroom, two bedrooms and laundry. Wifi/Bedding/Cookware/Bath Accessories/One Free Parking Spot on the driveway and free street parking (ONLY Available Apr-Nov). This is a great choice for your family summer/winter vacation! A few minutes' drive to downtown Barrie and beautiful Lake Simcoe waterfront, various restaurants, Costco, Walmart and unique shops.

FamilyKitchenGetting around

4.79 out of 5 average rating, 395 reviews
Guest favorite
Home in Barrie

HotTub PoolTable Poker BBQ 10MinsToLakeSimcoe Luxe

Welcome to Prima, a thoughtfully curated 6-bedroom luxury escape built for entertaining and relaxing. Unwind in the private hot tub, fire up the BBQ, play pool or poker, enjoy games, immersive sound and a 75" Smart TV, or cook in the gourmet kitchen beneath soaring 10' ceilings. Minutes from restaurants, shopping, golf, Lake Simcoe and beach access, plus just 25 mins from Snow Valley and Horseshoe Valley Resort.

FamilyIndoor spacesAccuracy

4.96 out of 5 average rating, 113 reviews
Top guest favorite
Dome in Utopia

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 208 reviews

Popular amenities for Essa family-friendly rentals

Family-friendly home rentals with a pool

Top guest favorite
An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.
Guesthouse in Barrie

Warm rustic luxury chalet near lake and trails

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 105 reviews
Top guest favorite
Condo in Horseshoe Valley

Highland Grand Retreat Studio

KitchenFamilyParking

4.93 out of 5 average rating, 111 reviews
Top guest favorite
The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.
Condo in Blue Mountain Resort Area

Maple & Mountain | Pool/Hot Tub/Shuttle/WalkToBlue

FamilyKitchenBathroom

4.96 out of 5 average rating, 1028 reviews
Top guest favorite
A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.
Condo in Horseshoe Valley

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Indoor spacesKitchenCondition

4.99 out of 5 average rating, 137 reviews
Top guest favorite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Indoor spacesKitchenCheckout

4.96 out of 5 average rating, 404 reviews
Top guest favorite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono

The Trails Retreat (Private Cabin)

FamilyIndoor spacesGetting around

4.95 out of 5 average rating, 356 reviews
Top guest favorite
A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.
Cottage in Wasaga Beach

GATED RESORT COTTAGE

FamilyIndoor spacesLaundry

4.95 out of 5 average rating, 330 reviews
Top guest favorite
Condo in Innisfil

The Friday Flat | Sunny Escape by the Marina

Indoor spacesFamilyCheck-in

4.93 out of 5 average rating, 242 reviews

When is the best time to visit Essa?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$29,477 GYDG$29,686 GYDG$25,296 GYDG$28,432 GYDG$28,014 GYDG$28,223 GYDG$31,359 GYDG$35,958 GYDG$30,314 GYDG$29,059 GYDG$28,641 GYDG$29,059 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C