Holiday rentals in Simcoe County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Simcoe County

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Top guest favourite

A dining table is set with decorative blue and white dishware. In the background, a fire pit is surrounded by red chairs, with vibrant greenery and a wooden swing adding to the outdoor ambiance. A flower arrangement and candles enhance the table setting.

Cottage in Innisfil

Greystone cottage in Innisfil

Welcome to our charming cottage in Innisfil, just a short walk from beautiful Lake Simcoe. Enjoy a spacious backyard featuring a cozy fire pit, a peaceful swing, bicycles and a BBQ area perfect for relaxing evening. You’ll find a fun game room equipped with AC, pool table, air hockey for entertainment during your stay. Conveniently located near grocery stores, Home Hardware, restaurants at Friday Harbour, and other local amenities. Come experience the beautiful atmosphere with your loved ones.

ValueFamilyNearby

4.96 out of 5 average rating, 104 reviews

Top guest favourite

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...

FamilyValueBathroom

4.97 out of 5 average rating, 507 reviews

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

LocationFamilyAir conditioning

4.9 out of 5 average rating, 145 reviews

Top guest favourite

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

Cottage in Tiny

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

LocationValueIndoor spaces

4.97 out of 5 average rating, 133 reviews

Guest favourite

The glamping dome is set among vibrant autumn foliage, surrounded by a carpet of fallen leaves. The transparent dome showcases comfortable seating on the porch, inviting relaxation while blending with nature. The entrance reveals a cozy and welcoming atmosphere, with light filtering through the large windows.

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.

FamilyValueAmenities

4.95 out of 5 average rating, 293 reviews

Guest favourite

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

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.

LocationValueBeach

4.96 out of 5 average rating, 183 reviews

Top guest favourite

The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.

Guest house in Barrie

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

FamilyLocationAir conditioning

5.0 out of 5 average rating, 314 reviews

Top guest favourite

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.

LocationFamilyCleanliness

4.95 out of 5 average rating, 167 reviews

Top guest favourite

A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.

Place to stay in Wasaga Beach

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

LocationFamilyHot tub

5.0 out of 5 average rating, 418 reviews

Guest favourite

A modern living area is highlighted by a comfortable blue sofa and a matching armchair. A round coffee table sits in the center, with a decorative plant nearby. Natural light streams through large windows, enhancing the spacious feel of the room.

Home in Barrie

Luxury Home Mins to Lake & Beach

Welcome to Your Modern Retreat minutes away from the Lake and Beach! Experience comfort and style in our newly built, beautifully furnished 3-bedroom house, perfect for families, groups, or business travellers. Located in the heart of Barrie, our home offers a serene escape with all the amenities you need for a memorable stay. 50 m to nearest bus stop 1.5 km to grocery stores and Bayfield Mall 3 km to Downtown 4 km to Centennial Beach and Park 6 km to Johnson's Beach

ValueLocationPool

4.92 out of 5 average rating, 142 reviews

Top guest favourite

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.

FamilyLocationWifi

4.91 out of 5 average rating, 304 reviews

Superhost

The exterior of the cottage displays a modern architectural design with large floor-to-ceiling windows, allowing for ample natural light. A spacious wooden deck surrounds the front, featuring lush greenery and vibrant flowers, creating an inviting atmosphere for relaxation.

Cottage in Innisfil

Crystal Beach Cottage & Spa

**New Boat Launch 2026 In front Of Property** Serene lakefront cottage with breathtaking views! This cottage fronts on the East side & faces West for a mesmerizing sunrise & sunset. A few steps to the lake for a dip in the lake, sun bathing, paddle boarding (4 paddle boards) or a stroll up Innisfil Beach Park for a walk. An outdoor fire pit, sauna and hot tub awaits you at to relax and loosen up those muscles & release tension. A wonderful experience awaits you!

LocationValueBack garden

4.87 out of 5 average rating, 373 reviews