Home Vacation Rentals By Owner In Orillia, ON

Showing 40 Of 49 Vacation Rentals
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$73.7

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Apartment

TreeTop Two Bedroom Sophistication

Orillia, Ontario, Canada

Enjoy all the comforts of home in this newly renovated, fully equipped, elegantly appointed two-bedroom apartment. The building is tucked away on a calm, family friendly street, minutes away from all the amenities. This unit provides everything you need for a comfortable stay in beautiful Orillia, Ontario!brbrThe unit features a fully equipped custom kitchen, a full bathroom with heated floors & double sink vanity, air conditioning, Dishwasher, Washer/Dryer, Wifi & a brand new 65 smart TV with all the popular streaming apps. Netflix and Amazon Prime included. The bathroom, kitchen, an entry all have heated floors for increased comfort. brbrThe primary bedroom has a queen size bed with large under bed storage and a large mirror closet. There is a second room with a double/twin bunk bed with under drawer storage, plus closet.brbrThe property is ideally located in Orillia. br- 10 minute walk from the Couchiching Beach at Lake Simcoebr- 4 minute walk from the Orillia library, opera house and farmers marketbr- 5 minute walk from downtown Orilliabr- 5 minute walk from Orillia Soldiers’ Memorial Hospitalbr- 4 minute drive from Orillia Recreation Centrebr- 5 minutes off highway 11brbrGuests have access to the entire unit. brParking can be made available upon request. Note that this unit is located in a small multi-unit building.brbrHouse rules:br* Parties and events are NOT allowed br* Only registered guests are allowed at the property. Exceptions can be made, but only with proper advanced notice and transparency. br* Capacity 4 guests. Maximum 2 adults pleasebr* Quiet hours in place from 10pm to 8am
Bed 2

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Bath 1

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Sleep 4

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$67.2

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Apartment

Modern Sun-Filled 2nd Story

Orillia, Ontario, Canada

Enjoy all the comforts of home in this newly renovated, fully equipped, elegantly appointed one-bedroom apartment. The building is tucked away on a calm, family friendly street, centrally located just a quick walk away from all the amenities. This unit provides everything you need for a comfortable stay in beautiful Orillia, Ontario!brbrThe unit features a fully equipped large custom kitchen, a full bathroom with heated floors, air conditioning, Dishwasher, Washer/Dryer, Wifi & a brand new smart TV with all the popular streaming apps. Netflix and Amazon Prime included. Heated floors in the bathroom and main entry. brbrThe property is ideally located in Orillia. br- 10 minute walk from the Couchiching Beach at Lake Simcoebr- 4 minute walk from the Orillia library, opera house and farmers marketbr- 5 minute walk from downtown Orilliabr- 5 minute walk from Orillia Soldiers’ Memorial Hospitalbr- 4 minute drive from Orillia Recreation Centrebr- 5 minutes off highway 11brbrGuests have access to the entire unit. brParking can be made available upon request. Note that this unit is located in a small multi-unit building.brbrHouse rules:br* Parties and events are NOT allowed br* Only registered guests are allowed at the property. Exceptions can be made, but only with proper advanced notice and transparency. br* Capacity 3 guests. Maximum 2 adults pleasebr* Quiet hours in place from 10pm to 8am
Bed 1

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Bath 1

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Sleep 3

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Exceptional(2)

$397.12

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Cottage

Charming waterfront cottage. Lake Couchiching Casino Rama/ski resorts.

Orillia, Ontario, Canada

Discover the perfect blend of natural beauty, outdoor adventure, and comfort at our charming waterfront cottage on Lake Couchiching. Whether you're looking for a peaceful retreat or an active getaway, this cozy yet spacious cottage is ideal for families, friends or couples. With breathtaking views, nearby attractions, and plenty of outdoor fun, you’ll find everything you need for an unforgettable stay.brbrNestled on the shores of Lake Couchiching, our cottage offers an unbeatable location just minutes from the excitement of Casino Rama and local ski resorts. Enjoy quiet mornings on the lake, afternoons filled with swimming, kayaking or paddleboarding, peaceful evenings by the fire, or thrilling nights at the casino or on the slopes – this destination truly offers something for everyone.brbrLarge front windows offer incredible views of the lake, making every moment feel special. Whether you're inside or outside, you'll never be far from nature’s beauty. brbrThe open-concept living area features comfortable seating, and large windows that bring the outdoors in. It’s the perfect space for relaxation after a day on the water. brbrPrepare delicious meals with ease in the modern, fully stocked kitchen. Enjoy them in the dining area or step outside for al fresco dining on the deck with lake views.brbrGet active on the water with our provided kayaks, canoe and paddleboards. Explore the calm, clear waters of Lake Couchiching or enjoy a relaxing paddle while taking in the stunning surroundings.brbrStep directly onto the water from the cottage’s private dock. Perfect for swimming, fishing, or simply unwinding by the water.brbrThe expansive yard offers plenty of space for outdoor games like cornhole, frisbee, and lawn games, or simply relax in the sun with a good book.brbr Inside, you'll find a variety of board games, puzzles, and cards for family-friendly entertainment. Outside, enjoy the expansive yard and the lakefront for even more opportunities to play and relax.brbrAfter a day of adventure, cozy up and enjoy movies or shows on the flat-screen TV, with access to popular streaming services.brbrA short drive away, Casino Rama offers gaming, live entertainment, and a range of dining options.brNearby ski resorts offer skiing and snowboarding just a short distance from the cottage.brExplore nearby trails for hiking, biking, or snowshoeing, depending on the season.brbrWhether you seek adventure on the lake, thrilling nearby attractions, or simply a relaxing getaway with stunning views, our waterfront cottage on Lake Couchiching offers it all. Book your stay today and create lasting memories in this idyllic lakeside retreat!brbr
Bed 5

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Bath 1

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Sleep 8

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Exceptional(23)

$407.28

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Cottage

Redwood Retreat Waterfront Cottage By Simcoe With Hot Tub And Sauna

Orillia, Ontario, Canada

This 4-season Lake Simcoe waterfront cottage offers stunning lake views and crystal-clear water perfect for swimming. With plenty of outdoor space and activities, it’s ideal for families, friends, and small groups. Enjoy peaceful sunsets, summer fishing, winter ice skating, and year-round water fun. The cottage is only 1–1.5 hours from the GTA and 15 minutes from the casino. Kids will also love the cozy wooden bunkhouse by the water.brbrThe cottage is designed for relaxation and comfort, featuring 5 bedrooms (1 king and 4 queen beds) and a backup electric generator for peace of mind during power outages. Enjoy the private hot tub and sauna, outdoor playground for kids, and a variety of water activities.brbrStay connected with high-speed internet and a smart TV. Summer highlights include fishing, boating, and watching the most beautiful sunrises on Lake Simcoe. We provide 3 kayaks, 3 paddles, and 1 paddleboard for exploring the peaceful lake.brbrIn winter, enjoy sledding, ice fishing, skating, and even playing hockey on the frozen lake—then warm up in the hot tub and sauna. This cottage offers the perfect all-season getaway for unforgettable memories.brPlease kindly review our cottage rules to ensure a safe and enjoyable stay for everyone:brbr• Fireworks, Roman candles, and any type of explosives are strictly prohibited on the property.br• Early check-in and late check-out may be available for an additional fee.br• Children must not be left unattended near the water at any time.br• Kids must be supervised at all times for their safety.br• Please be respectful of our neighbours and keep noise to a considerate level.br• Kindly inform us in advance if you plan to add any additional guests to your group.br• Maximum capacity: 10 guests during the day and 8 guests overnight, as required by local by-laws.br• Kayaks must be tied up and pulled out of the water after use to prevent them from drifting away. Guests are responsible for the replacement cost if kayaks are lost.br• One garbage bag is included per 2-night stay. Additional bags will incur a $20 fee each.brbrThank you for your cooperation — we truly appreciate your help in keeping the cottage safe, clean, and enjoyable for everyone.
Bed 5

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Bath 2

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Sleep 8

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Exceptional(34)

$1238.32

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Cottage

Lazy_Bear_Orillia Waterfront Log Home

Orillia, Ontario, Canada

Our stunning 6-bedroom luxurious lakefront log home is on Lake Couchiching. Located in the town of Orillia, it is the perfect getaway from the hustle and bustle of the City. We are conveniently located close to Casino Rama, Amigo beach, and Tudhope Park.brbrThe open-concept design on the main level is flooded with natural light thanks to the cathedral ceilings and floor to ceiling windows that offer spectacular views of the lake and picturesque sunsets. We have a paddle boat and kayaks.brThe spacebrThe kitchen offers all the amenities of home including modern, stainless steel appliances and a huge pantry with all your basic essentials.brbrFeatures: Cathedral ceiling, Leather couches, Antique coffee table, Flat screen TV with Chromecast, stereo and CD player with Yamaha surround-sound system. We have a game room with a ping pong, air hockey and pool table.brbrThe kitchen opens up to the dining area with a beautiful, large wooden table that can accommodate eight people. The living room is bright and spacious with ample, lush sofas for the entire group to relax and unwind. The room also offers a wood-burning fireplace and a flat screen TV with Chromecast HD TV.brbrThe Cottage has six bedrooms and 3.5 bathrooms. The master bedroom is located on the main floor with a 5-piece ensuite, stunning air jacuzzi bathtub, custom-made log-style King bed with built in walk in closet. On the second floor, there are three large bedrooms, two of which have queen beds with balconies, a third with bunk beds as well as a twin bed. There is a 5-piece bathroom with a jacuzzi tub in the hallway. In the basement we have two bedrooms with queen beds and bathroom located in the hallway with bathtub and shower.brbrThe basement offers an entertainment room equipped with game room with big screen TV. The basement has a walkout to the backyard. The backyard features a stunning stone deck and patio, perfect for lounging on in the summer! We are close to shops, cafe’s, restaurants, movies and attractions. It is a perfect getaway for up to 16 people and only an hour and half hour drive from Toronto. Lounge on the dock or go for a dip in the lake, take the paddle boat out or the canoes for a fun adventure on the lake. Friends and families can enjoy outdoor activities, firepit, sauna without even leaving the property. There are a plethora of activities in the area within minutes of the Cottage, including golf courses, miles of hiking/biking trails, skiing, snowmobiling, ATV trails and more.brbrA truly relaxing and unforgettable getaway awaits you! Outdoor Cameras are on premises. Brand new fire pit and sauna.
Bed 7

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Bath 3

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Sleep 16

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Exceptional(51)

$408.24

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Private Vacation Home

Big Yellow House on Lake Couchiching in S. Muskoka & Orillia

Orillia, Ontario, Canada

The Cape Cod-style home is right on the water and is meant for family enjoyment. (not a party house please) 4 bedrooms, a gorgeous living area and a breathtaking view of the lake! The gorgeous house has an L Shaped dock (in summer) which is great to sit on on a Muskoka chair with a glass of wine to wonders of nature!brbrLocated in Cumberland Beach is a small village just north of Orillia. It is a very 2km drive from the famous Weber’s Burgers and about a 20-minute drive to Casino. From the rear window, you can see the popular Big Chief island.brbrCome inside to see a fully functional kitchen and large open kitchen space, or sit on the large deck under the umbrella or in the sun and watch the ducks, birds (Blue Jays, Orioles and Hummingbirds) and other wildlife living their best life. At night there is a nice fire pit for your enjoyment.brbrThere is also a gas-powered BBQ with a sitting area outside for nice meals outside.brbrOn rainy days, you can sit inside and enjoy movies or stream from your favourite service on the big screen tv.brbrNote that our capacity for the house is 8 people. 3 of the bedrooms are upstairs. There is a king-size bed, a queen in the 2nd bdrm. The 3rd bedroom has 2 Queen beds or for those that prefer more privacy, there is a 4th bedroom that has bunk beds on the main floor.brbrFor those that love to swim the water is generally around knee deep for the first 100m and then it drops off. Enjoy the paddle boards, canoe or paddle boat and we encourage you to bring water shoes for the sandy/mushy bottom.brbrThis is a quiet community with neighbours so we do discourage any groups that plan on playing loud music or using the house for any reason other than enjoying the environment.brbrThere are also fruit markets and a local convenience store within walking distance and a boat slip for anyone bringing a boat. For those that plan on using the fire pit, make sure to get some wood on the way up Highway 11!brbrIf you have any other questions please feel free to reach out! We look forward to hosting you!brbrFinally - we do like to communicate with our potential guests before completing any bookings. So if you are interested please send us a message first and we can answer any questions you may have. Please DO NOT just book the property without having spoken to us first. Thanks!
Bed 4

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Bath 2

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Sleep 10

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Exceptional(1)

$347.0

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Private Vacation Home

Cozy, Modern Home Close to Public Beach and Downtown Orillia

Orillia, Ontario, Canada

Relax in Comfort at This Renovated Family Home in the Heart of OrilliabrbrWelcome to your home away from home in beautiful Orillia! Nestled on a peaceful residential street just minutes from Lake Simcoe and downtown, this fully renovated, detached family home offers the perfect blend of modern comfort, thoughtful amenities, and convenience. With 4 cozy bedrooms, 2 full bathrooms, and a fully equipped kitchen, our home is designed to make your stay as comfortable and effortless as possible—ideal for family getaways, small groups, or anyone looking to unwind and reconnect.brbrFrom the moment you arrive, you’ll notice the calm and inviting atmosphere. This spacious home comfortably accommodates up to 8 guests (including children) and offers everything you need for a relaxing and memorable stay. Whether you're in town for a summer adventure or simply to recharge in a quiet setting, you'll feel right at home here.brbrInside, you’ll find two spacious master bedrooms with queen-sized beds and two additional bedrooms each featuring double beds—perfect for families or groups of friends. The main floor bathroom boasts a fully updated 4-piece layout, including a bathtub and roomy shower. Downstairs, you’ll find a second full bathroom with a standing shower.brbrWhether you're whipping up a gourmet family meal or grabbing a quick bite before heading out, the kitchen has everything you need - pots, pans, utensils, dish ware, and even a dishwasher for easy cleanup. We've also included an extra fridge and freezer on the lower level, perfect for storing additional groceries, drinks, or local market finds during longer stays. Enjoy meals inside or step out onto the private back deck, where you’ll find two inviting outdoor seating areas, a large BBQ, and a beautifully designed fire pit surrounded by classic Muskoka chairs.brbrThe home is outfitted with three smart TVs spread throughout, giving you plenty of options for relaxing with your favorite shows or movies (just bring your own streaming logins). Unlimited Wi-Fi ensures a seamless connection for work, school, or entertainment. We’ve also included a selection of board games to bring everyone together on cozy evenings or rainy days.brbrOutside you will find a new deck and two outdoor seating areas offer plenty of space to relax. Fire up the BBQ for a summer cookout, or gather around the fire pit, where you’ll find Muskoka chairs, a stash of firewood, and all the supplies you need for a cozy, country-style campfire. It’s the perfect spot for s’mores, storytelling, and stargazing. Depending on the time of year, help yourself to fresh herbs and veggies from the seasonal garden—a little bonus touch to enhance your meals and make you feel at home.brbrThere’s room to comfortably park up to 4 vehicles in the private driveway, with additional overnight street parking available during the summer months. The home is fitted with central air conditioning and heating, ensuring year-round comfort. You’ll also find a washer and dryer on-site, making longer stays a breeze.brbrHighlights of the Home:br- Sleeps 8 guests (including children)br- 4 bedrooms: 2 queen beds, 2 double bedsbr- Fully stocked kitchen with dishwasherbr- Central A/C & heatingbr- Unlimited high-speed Wi-Fibr- 3 smart TVs with streaming apps (log in with your own credentials)br- Washer & dryer on the lower levelbr- Additional fridge and freezer for extended staysbr- Municipally sourced tap waterbrbrOutdoor Features:br- Private back deck with seating and BBQbr- Gorgeous fire pit with firewood and supplies providedbr- Fresh herb and veggie garden (seasonal)brbrLocation, Location, Location: You’ll be just minutes from everything Orillia has to offer:br- 15-minute walk to Moose Beach/Tudhope Park and public boat launch at Lake Simcoebr- 5-minutes to charming Downtown Orilliabr- 10-minutes to Casino Ramabr- Close to hiking trails, bike paths, beaches and more.brbrGood to Know:br- This home is fully licensed and follows City of Orillia STR bylaws. To adhere to the requirements outlined by the City, all guests will be required to sign and submit a guest code of conduct form prior to your stay.br- We welcome up to 2 well-behaved dogs (must be disclosed before booking; $50 cleaning fee applies).br- Linens and towels are provided—please bring your own beach towels.br- Up to 4 vehicles can park in the driveway; free overnight street parking is available in summer.br- Local beaches are monitored for water quality; please follow posted signs.brbrHouse Rules:br- Maximum 8 guests (including children)br- No parties or smoking on the propertybr- No fireworks or unauthorized fires (use the designated fire pit only)br- Pets must be disclosed in advancebr- Towels provided must remain inside the homebrbrWhether you’re here to explore all that Orillia has to offer, or simply to enjoy the peaceful comforts of a beautifully cared-for home, we’ve thought of every detail to make your stay smooth, relaxing, and full of great memories. Just bring yourselves—we’ll take care of the rest.brbrWe can’t wait to host you!
Bed 4

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Bath 2

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Sleep 8

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Exceptional(23)

$765.44

/ Nightly
Cottage

Luxurious All-season Simcoe Lakefront Cottage

Orillia, Ontario, Canada

A luxurious all-season family lakefront cottage with 100'+ of private shoreline on Lake Simcoe. An open-concept, gourmet kitchen, million-dollar views, and custom furniture and finishings throughout. Great for summer and winter family getaways, vacations, celebrations, and reunions. Just a 60 min. drive from the GTA.brbrLONG TERM WINTER RENTAL IDEAL FOR FAMILY WINTER SPORTS LIKE SKIING AND SNOWSHOEING IS AVAILABLE. An open-concept, gourmet kitchen, million-dollar views, and custom furniture and finishings throughout. Great for summer and winter family getaways, vacations, celebrations, and reunions. Just a 60 min. drive from the GTA.brbrThe all season lakefront cottage is ideal for:brbr+ Family and friend gatherings, celebrations, reunions, and vacationsbr+ Lakefront for swimming, canoeing, kayaking, fishing, snow shoeing, cross-country skiing, ice-fishingbr+ Ski & Mountain Biking Trips, Horseshoe Valley, Mount St. Louis Moonstone, Hardwood Ski & Bikebr+ Golf Trips (Hawk Ridge, National Pines & Trehaven golf courses)br+ Hiking Trips (Scout Valley Loop Trail, Simcoe County Forest - Breedon & Rogers Tract)br+ Close to shopping and restaurants in Orillia brbrNOTABLE FEATURESbrbr+ Hot tub br+ 4 LCD TV's & Cablebr+ Gourmet Kitchenbr+Premium Mattressesbr+Stone Fireplacebr+Pool Table br+ Ping Pong Tablebr+ Board Gamesbr+ Large Dockbr+ Firepitbr+ Muskoka Chairsbr+ Spacious patio overlooking Lake SimcoebrbrINDOOR FEATURESbrbr+ 3000 sq. ft. of luxurybr+ 5 spacious bedroomsbr+ 7 comfortable beds + 2 futonsbr+ 3 full bathroomsbr+ 4 HDTVs throughout (55'-75') with AV jacks.br+ Gleaming hardwood floors and siding.br+ High speed wifi, Rogers Cable TV, great cell reception.br+ Incredible stone gas fireplace in Great Roombr+ One of a kind Gourmet Kitchen with high end appliancesbr+ All the cookware and dinnerware necessary to make gourmet mealsbr+ Oversized custom-made dining tablebr+ Incredible views of Lake Simcoe br+ Large desk and printerbr+ Washing machine and dryerbrbrOUTDOOR AMENITIESbrbr+ Huge lakeside grassy yard w/ Fire Pit - firewood providedbr+ Hot tub (open summer and winter)br+Oversized natural gas Weber BBQbr+ Ping pong tablebr+ Canoe, kayak, paddle board, and row boat (great for fishing) (life jackets provided)br+ Direct access to the lake from the dock or via sandy beachbr+ Outdoor patio set overlooking the lakebr+ 2 outdoor lounge bedsbr+ Spectacular lake for swimming, fishing, boating in summer and snow shoeing and cross country skiing in winterbrbrNote: This listing is for information purposes only. Neither the listing nor the photos may be accessed, downloaded, scraped, indexed, crawled, or collected for any purpose including any commercial purpose.
Bed 5

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Bath 3

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Sleep 10

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