
Simcoe County long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Simcoe County. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Simcoe County are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Simcoe County
Showing deals for:15 Feb - 15 Mar
Image gallery for Lovely Newly Built Cottage by the Water

Lovely Newly Built Cottage by the Water
Severn
Image gallery for Family Getaway On Lake Couchiching - Perfect for family time

Family Getaway On Lake Couchiching - Perfect for family time
Severn
Image gallery for Cottage with Private Beach Access and Newly-Built Indoor Sauna #STRTT-2026-114

Cottage with Private Beach Access and Newly-Built Indoor Sauna #STRTT-2026-114
Tiny
Image gallery for "Tiffany" Cottage w/ Hot Tub & Barrel Sauna

"Tiffany" Cottage w/ Hot Tub & Barrel Sauna
Severn
Image gallery for The Relaxation Station

The Relaxation Station
Tiny
Image gallery for Lakefront Cedar Haven- Free use Canoe and Kayak, 1 hr from Toronto

Lakefront Cedar Haven- Free use Canoe and Kayak, 1 hr from Toronto
Springwater
Image gallery for Lakeside Luxury on Lake Muskoka – Stunning Home with Dock, Beach & Views

Lakeside Luxury on Lake Muskoka – Stunning Home with Dock, Beach & Views
Gravenhurst
Image gallery for "Take It Easy" cottage w/ Hot Tub & Finnish Sauna

"Take It Easy" cottage w/ Hot Tub & Finnish Sauna
Severn
Image gallery for Modern Family Friendly Chalet

Modern Family Friendly Chalet
Oro-Medonte
Image gallery for 6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ

6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ
Innisfil
Image gallery for The raw beauty of Georgian Bay waterfront home

The raw beauty of Georgian Bay waterfront home
Tiny
Image gallery for The Pearl Cozy Beach House/Blue Mountain Ski Hills 4 Season Vacation Destination

The Pearl Cozy Beach House/Blue Mountain Ski Hills 4 Season Vacation Destination
Wasaga Beach
Image gallery for Cheerful 4-bedroom cottage in nature setting

Cheerful 4-bedroom cottage in nature setting
Tay
Image gallery for "beachcomber" Cottage

"beachcomber" Cottage
Severn
Image gallery for Gorgeous and spacious Winfield Chalet just steps away from Georgian Bay!

Gorgeous and spacious Winfield Chalet just steps away from Georgian Bay!
Tay
Image gallery for "Balmoral" Cottage

"Balmoral" Cottage
Severn
Image gallery for Muskoka Honey Harbour Private Lake Front with Hot Tub!

Muskoka Honey Harbour Private Lake Front with Hot Tub!
Georgian Bay
Image gallery for Canyon Connection Chalet - Pool Table + Mountain View!

Canyon Connection Chalet - Pool Table + Mountain View!
The Blue Mountains
Image gallery for Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
Innisfil
Image gallery for Sunrise Villa on the Lake

Sunrise Villa on the Lake
Innisfil
Image gallery for Make memories at the Jansen Clan Cottage

Make memories at the Jansen Clan Cottage
Wasaga Beach
Image gallery for BEACHFRONT wasaga paradise, 30min to collingwood/blue mountain, large backyard

BEACHFRONT wasaga paradise, 30min to collingwood/blue mountain, large backyard
Wasaga Beach
Image gallery for Waterfront & Pvt Beach 120’Shoreline: SHALLOW/Sandy: Perfect for Little Kids!

Waterfront & Pvt Beach 120’Shoreline: SHALLOW/Sandy: Perfect for Little Kids!
Ramara
Image gallery for Shale Beach House -- 5 minutes drive to Blue Mountain Village!

Shale Beach House -- 5 minutes drive to Blue Mountain Village!
The Blue Mountains
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Simcoe County
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Simcoe County Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Simcoe County come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Simcoe County
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Simcoe County with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Simcoe County
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Simcoe County with flexible cancellation policies.