Tiny house vacation rentals in Simcoe County

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Top-rated tiny house rentals in Simcoe County

Guests agree: these tiny house rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A wooden dock extends over a serene pond, featuring two black Adirondack chairs positioned for relaxation. In the background, gentle hills are lined with trees, and a decorative fountain creates soft ripples in the water under a cloudy sky.

Tiny home in MONO

4.92 out of 5 average rating, 124 reviews

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 for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

Top guest favorite

A quaint blue cottage features a welcoming front deck with two yellow chairs facing the lush green lawn. The cottage is surrounded by trees and showcases large windows that bring natural light into the interior.

Tiny home in Waubaushene

5 out of 5 average rating, 175 reviews

Saltbox by the Bay | Vetta/Tay Shore Trail/Bikes

Welcome to Saltbox by the Bay, your 4-season escape. A perfect couple's getaway or small family, group of friends or solo retreat. This vintage cottage is upcycled with luxe amenities. Make gourmet meals, listen to albums, play boardgames & watch sunsets over the bay. Explore the treats of cottage country: hike or bike the Tay Shore Trail, visit Quayle's Brewery & Wye Marsh, pamper yourself at Vetta Nordic Spa & enjoy one of the nearby towns for restaurants & local amenities, just minutes away.

Top guest favorite

An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.

Tiny home in Gravenhurst

4.98 out of 5 average rating, 159 reviews

Woodland Muskoka Tiny House

Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft tiny home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka. The three season, screened in porch invites you to enjoy your coffee (or wine!) in nature without being bothered by the mosquitos!

Guest favorite

A rustic kitchen space features a wooden counter with twin sinks. Stone walls provide a natural texture, while wooden cabinets above hold various bottles. Sunlight filters through a nearby window, illuminating the earthy tones of the cabinetry and decor.

Cottage in Victoria Harbour

4.81 out of 5 average rating, 190 reviews

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.

Guest favorite

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

Tiny home in Horning's Mills

4.9 out of 5 average rating, 167 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

Follow the forest pathway to our 2 new 'glamping bunkies'. The Owl’s Roost features a large loft and treetop deck to surround you with the beauty of nature. Just 1 hr from Pearson and 45 min. to Georgian Bay, Mulmur straddles the Niagara Escarpment, a UNESCO World Biosphere. We are next to 400 acres of conservation land in the Pine River Valley including part of the Bruce Trail. Our site can accomodate families, friends or groups. Not a camper? Please consider our 'in house' listings.

Guest favorite

The inviting interior features wooden walls with large windows allowing natural light to illuminate the space. A compact kitchenette is visible with appliances, while stylish stools complement a natural wood countertop. A cozy seating area with a futon sits adjacent to a wooden staircase leading to the loft.

Guesthouse in Shanty Bay

4.86 out of 5 average rating, 101 reviews

New Charming tinyhome Experience

Come spend a few days in our warm and cozy hideaway. Enjoy the winter wonderland with some Snow shoeing, cross country skiing or Snowmobiling right from your backyard! OR, perhaps you would like to go to the new Vetta Spa only mins away. Or downhill, snowboard at Horseshoe or Moonstone? OR maybe you just want to disconnect from technology for awhile and reconnect with yourself or loved one. Please inquire if you would like more than 3 guests. The options are plentiful from this location.

Superhost

A serene beach scene is presented, showcasing gentle waves lapping at the shoreline. The wet sand reflects the colors of the sky, where clouds vary in shades of pink and blue. Seagulls can be seen walking along the water's edge, adding to the tranquil atmosphere.

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.

Superhost

A charming wooden cabin is nestled among the greenery, featuring a small porch and decorative flower boxes under the windows. The exterior displays a rich, warm wood finish, complemented by a dark metal roof, creating a cozy glamping atmosphere in the country.

Campsite in Midland

4.8 out of 5 average rating, 125 reviews

Bunkie In Paradise!

It’s a bunk house for two. A little guest bedroom on our property in the country. I look at as a glamping get away. You can enjoy like camping with out having to sleep in a tent. Enjoy cooking outside, relax by a fire at night. We have trails,fish pond,pool. We are 15 minutes away from Coldwater,Midland,Horseshoe Valley,Port Severn. All have great local attractions.Great food and shopping! It’s a short drive for those who like to bike the Tay trail system of Georgian Bay.

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 275 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2025-008

Guest favorite

A tranquil sandy beach extends to the calm waters of Georgian Bay, reflecting the clear blue sky. A fire pit is visible among stone seating, with some rocks scattered along the shoreline. The peaceful scenery invites relaxation and enjoyment of the natural surroundings.

Cottage in Lafontaine

4.83 out of 5 average rating, 241 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! Note: pool is closed October to mid May.

Top guest favorite

The interior of the cabin features warm wooden walls and a high ceiling. A spacious bed with a plaid coverlet is centered against the wall. A cozy seating area is arranged nearby, and a small kitchenette is equipped with essential cooking tools. Natural light filters through the windows.

Cabin in Severn

5 out of 5 average rating, 129 reviews

Romantic Cabin Getaway with Hot Tub

Are you seeking a romantic getaway nestled in the serene beauty of nature? Look no further than our secluded cabin in the forest, providing complete privacy, and a rustic charm. You’ll find everything you need to relax & unwind. At Alive Wilderness Retreat we believe that the natural beauty of the forest provides the perfect backdrop for creating lasting memories.

Guest favorite

A small wooden cabin with a sloped metal roof sits among tall trees, surrounded by soft forest floor. A wooden bench and a picnic table are positioned in front, with a potted plant on the table. Sunlight filters through the branches, illuminating the natural setting.

Cabin in Mono

4.91 out of 5 average rating, 129 reviews

Evergreen Holler Forest Retreat

Welcome to Cedar & Bough! If you like tall pines, whispering winds and sunlight filtering through the trees, this spot is perfect for you! Evergreen Holler offers an immersive forest experience without having to trek into the woods yourself. Enjoy a private, peaceful and replenishing stay any time of the year in this off grid tiny home!