Simcoe Area Rentals
From $344 per night (USD)VRBO
Beautiful beachfront cottage on bass lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Situated on beautiful bass lake where your family vacation begins. Sit out under the stars and listen to beautiful bass ...
From $344 per night (USD)VRBO
From $448 per night (USD)Expedia
Cozy & Spacious Retreat I Sleeps 12 | Beach • Ski • Golf • Hiking • BBQ ⭐
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Cozy Lakeside Retreat Your perfect escape from city life and a comfortable home base to experience everythi ...
From $448 per night (USD)Expedia
From $197 per night (USD)VRBO
Your Friday Harbour Escape Awaits!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This spectacular, 2 bdrm/2bath model suite at the brand new Sunseeker @ Friday Harbour! Enjoy large terrace facing the ...
From $197 per night (USD)VRBO
From $536 per night (USD)VRBO
Spacious 1 BR | Living Water Resort and Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $536 per night (USD)VRBO
- From $267 per night (USD)
VRBO
3BR Barrie Home Near Downtown & Arena
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Settled-in 3-bedroom home minutes from downtown Barrie, well-suited for hockey teams and coaching staff at Sadlon Arena ...
From $267 per night (USD)VRBO
From $136 per night (USD)VRBO
Apartment, Cozy for a Happy Rest (basement)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our cozy apartment in the city! A private bright, modern and new space. It is the perfect choice for those se ...
From $136 per night (USD)VRBO
From $550 per night (USD)VRBO
Spacious Studio | Living Water Resort and Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $550 per night (USD)VRBO
From $620 per night (USD)VRBO
Spacious 2 BR | Living Water Resort and Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $620 per night (USD)VRBO
From $707 per night (USD)VRBO
Newly Renovated Beach Condo with Salt Water Pool Right on Wasaga Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Newly renovated 4-bedroom condo right on Wasaga Beach! You won't be disappointed when you walk in and see the spectacula ...
From $707 per night (USD)VRBO
From $440 per night (USD)Expedia
Georgian Bay 5 bedroom waterfront , large deck .Quiet family neighbourhood.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Bring the whole family .Waterfront on Georgian Bay in Victoria Harbour. 1.5 hours from Toronto. 5 bedroom sleeps 10 full ...
From $440 per night (USD)Expedia
From $332 per night (USD)VRBO
Clearview Ranch Estates UNIT 3 only
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect for couples, families, or business travelers, this bright studio sleeps up to 10 with 2 queen beds, 2 twin-over- ...
From $332 per night (USD)VRBO
From $502 per night (USD)VRBO
Clearview Ranch Estates UNIT 2 only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to Unit 2 at Clearview Ranch Estates—a cozy two-bedroom retreat perfect for families, couples, or small groups. ...
From $502 per night (USD)VRBO
From $604 per night (USD)VRBO
Clearview Ranch Estates UNIT 1 only
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Perfect for families, teams, and group getaways, Unit 1 features 4 bedrooms, 2 bathrooms, a fully equipped kitchen, spac ...
From $604 per night (USD)VRBO
From $634 per night (USD)Expedia
Life's a Beach House -Perfect beachfront vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Wake up just steps from the soft sand and sparkling waters of Balm Beach. This charming beachfront getaway offers the pe ...
From $634 per night (USD)Expedia
From $266 per night (USD)VRBO
Lake Getaway in Barrie
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your spacious Barrie getaway! Thoughtfully designed for families and groups, this 4-bedroom, 2.5-bath home s ...
From $266 per night (USD)VRBO
From $409 per night (USD)Expedia
Cozy Couples` Loft in the Heart of Collingwood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About this space A warm, characterful room for people who notice the details. The Foundry is a luxury loft-style one-be ...
From $409 per night (USD)Expedia
From $806 per night (USD)VRBO
Zenith Nest - 8 Beds, 3.5 Baths, 10 Park, BBQ, Large Patio
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to Zenith Nest, a bright, elegant, cottage-style retreat designed for large families & groups. Sun-filled, spaci ...
From $806 per night (USD)VRBO
From $142 per night (USD)VRBO
Cranberry Après Nest | Bright Collingwood Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to Cranberry Après Nest, your home base in the heart of Cranberry Resort (Living Stone). You’re minute ...
From $142 per night (USD)VRBO
From $200 per night (USD)VRBO
Cozy 1-bedroom bungalow in tranquil Barrie with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Barrie at this serene bungalow. Inside, guests find one bedroom with a king bed, perfect for ...
From $200 per night (USD)VRBO
From $385 per night (USD)Expedia
Chic Studio for Two, Steps from Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small on footprint, big on character. The Ledger is a luxury studio for two on the second floor of The Brick & Beam, a b ...
From $385 per night (USD)Expedia
From $436 per night (USD)VRBO
Romantic King Suite, Gas Fireplace, Chef`s Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The room you book to mark something. The Carmichael is the flagship luxury suite at The Brick & Beam, a boutique hotel i ...
From $436 per night (USD)VRBO
From $418 per night (USD)Expedia
Modern Industrial Retreat, Bakery Right Below
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About this space Some mornings you wake to the smell of bread rising up through the floor. The Hearth sits just above B ...
From $418 per night (USD)Expedia
From $343 per night (USD)VRBO
Spacious Modern Orillia Family Retreat- Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 14
Welcome to your perfect getaway at Searidge Street in Severn, Ontario! This expansive 5-bedroom home is ideal for famili ...
From $343 per night (USD)VRBO
From $451 per night (USD)VRBO
Waterfront Cottage-Muskoka Room, Hot tub & Firepit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your Muskoka Port Severn year round destination is perfect for fishermen, skiers, nature enthusiasts or those just looki ...
From $451 per night (USD)VRBO
From $932 per night (USD)VRBO
Beachfront Estate Perfect For Large Families In The Heart Of Balm Beach
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 18
Lakefront property in the heart of Balm Beach, minutes from Midland. The property features a 4 bedroom plus loft main h ...
From $932 per night (USD)VRBO
From $514 per night (USD)Expedia
Lost in Hillsdale | 10 mins to Horseshoe Valley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
🏡🌲 Lost in Hillsdale | Spacious Getaway Near Horseshoe Valley Welcome to Lost in Hillsdale — a bright and spacious 4- ...
From $514 per night (USD)Expedia
From $731 per night (USD)VRBO
Indoor Heated Pool and Sauna Right on the River
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to your private Wasaga Beach oasis! This luxury riverfront cottage offers: 🌊 100 ft of private riverfront with ...
From $731 per night (USD)VRBO
From $289 per night (USD)Expedia
6 bed Elegant Farmhouse Oasis minutes to beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Stroud Beach House Whether you're planning a family vacation, a beach getaway with friends, or a relaxing we ...
From $289 per night (USD)Expedia
From $152 per night (USD)VRBO
Suite close to Barrie Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our charming 2-bedroom apartment, ideally situated near the tranquil shores of the lake and just a short walk ...
From $152 per night (USD)VRBO
From $569 per night (USD)VRBO
Large Four Season Georgian Bay Family Getaway: Hot tub, Beach, Ski
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Fairview Cottage, This four season countryside cottage nestled amongst the trees is an ideal choice for famil ...
From $569 per night (USD)VRBO
From $460 per night (USD)VRBO
Spacious 1 BR | Living Water Resort and Spa
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $460 per night (USD)VRBO
From $531 per night (USD)VRBO
Spacious 2 BR | Living Water Resort and Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $531 per night (USD)VRBO
From $352 per night (USD)VRBO
Classic Family Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy Lake Couchiching Cottage with Private Beach Access Escape the pace of everyday life and step back into a simpler t ...
From $352 per night (USD)VRBO
From $578 per night (USD)Expedia
Mount St. Louis Four Season Hideaway
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Escape the city and unwind at this beautifully renovated farmhouse nestled on 3 private acres of mature trees in the hea ...
From $578 per night (USD)Expedia
From $205 per night (USD)VRBO
Friday Harbour Condo | Resort Living
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a perfect getaway! Just bring a suitcase and enjoy! Only an hour from Toronto and minutes to Barrie with a resor ...
From $205 per night (USD)VRBO
From $334 per night (USD)Expedia
Sleeps 16 and more | Bedrooms with ensuite washrooms
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
House sleep 16 & more, each bedroom has ensuite washrooms for added convenience and comfort. It 2 minutes to Ski Valley ...
From $334 per night (USD)Expedia
From $510 per night (USD)VRBO
Cozy Lake Simcoe Waterfront Escape for 10
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 10
Settle into cozy lakeside living at our modern rustic Lake Simcoe retreat. Curl up by the fire and play poker after a da ...
From $510 per night (USD)VRBO
From $450 per night (USD)Expedia
The Kempenfelt: Luxury 4-Bedroom Forest Retreat Near Horseshoe Valley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to *The Kempenfelt*, a brand-new luxury home in Craighurst Crossing, Oro-Medonte, offering over 3,000 sq. ft. of ...
From $450 per night (USD)Expedia
From $416 per night (USD)VRBO
Modern Orillia Retreat - W/ Game Room
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 12
Welcome to The Evergreen Escape— Your Year-Round Modern Retreat in Severn, Ontario Nestled on the edge of Ontario`s lus ...
From $416 per night (USD)VRBO
From $424 per night (USD)Expedia
Rama Ridge with Basketball Court, Hot Tub, Sauna
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 12
Escape to Nature & Luxury – Minutes from Casino Rama Discover the perfect blend of countryside serenity and upscale com ...
From $424 per night (USD)Expedia
From $478 per night (USD)VRBO
Sunbank Escape With Hot Tub & Game Room
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 12
Discover the ultimate getaway at this newly built, stylish home near Menoke Beach, Ontario. With 4 spacious bedrooms, 8 ...
From $478 per night (USD)VRBO
From $318 per night (USD)Expedia
Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Cozy and lovely private Wasaga vacation cottage/home, fantastic location walking distance to sandy beach 2, the world lo ...
From $318 per night (USD)Expedia
From $188 per night (USD)VRBO
Executive Rental | 32 Oak Street, Collingwood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brand New Building! Experience sophisticated downtown living in this beautifully appointed executive rental at 32 Oak St ...
From $188 per night (USD)VRBO
From $424 per night (USD)VRBO
Spacious 5-bedroom cottage in fantastic Wasaga Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Your Wasaga Beach adventure begins at this 5-bedroom cottage. Step inside to a fantastic space where comfort meets charm ...
From $424 per night (USD)VRBO
From $188 per night (USD)VRBO
Private - Walkout Studio -Free Parking & Wifi- Events-Beaches-Skiing- Shopping!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private and easy check-in welcomes you into your side deck seating and entrance to the Studio suite, perfect for solo tr ...
From $188 per night (USD)VRBO