Vacation Rentals By Owner In Orillia, ON

Quiet and relaxing four seasons cottage, three bedrooms with a great view of Lake Simcoe from our large front deck. Relax on our waterfront property and swim in the clear sandy-bottom lake. All the comforts of home, including fresh filtered/treated soft water system, TV, dishwasher, washing machine and dryer.brbrMinutes away from historic and fun downtown Orillia, Casino Rama and several ski resorts. Lots of eating, shopping and outdoor adventures close by including skiing, ice fishing, hiking, bike/snowmobile trails, marina with jet ski and boat rentals and more. Come and relax in a comfortable cottage up in Simcoe Country. Several provincial parks nearby with quaint old towns along the way make a fun day of antique shopping and visiting farmers' markets.brbrBeautiful Lake Simcoe is on our property across from the front yard. Lake is clear, weed-free, sandy bottom, with a gradual shoreline for wading or young kids. 2 Kayaks are also provided.brbrLake completely freezes for ice fishing, skating, snowmobiles.brbrLarge garbage storage bin at end of the driveway. Please put your garbage/recycle in the storage bin as part of your check out. Garbage pickup is on Tuesday morning. br

Cute and relaxing cottage on the lake

Orillia, Ontario, Canada

Bed

Bath

6

Sleeps

$65.75

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!brbrDishwasher, Washer/Dryer, Wifi & a brand new smart TV with all the popular streaming apps. Netflix and Amazon Prime included. brbrThere is a queen size bed with large under bed storage and a closet. There is a pull-out sofa in the living room.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

Charming Sun Filled Custom Getaway

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$65.03

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 custom kitchen, a full bathroom with heated bathroom and Entry floors, air conditioning, Dishwasher, Washer/Dryer, Wifi & a brand new smart TV with all the popular streaming apps. Netflix and Amazon Prime included. The suite is a modern concept bedroom with no physical door, but separated from the main living area through its design. brbrThere is a queen size bed with under bed storage and a closet. There is a pull-out sofa in the living room.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 2 guests. Maximum 2 adults pleasebr* Quiet hours in place from 10pm to 8am

Modern Victorian Charmer

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$703.24

Escape to our charming 1.5-storey cottage, less than 1.5-hour drive from Toronto, located on the beautiful shores of Lake Simcoe. Enjoy stunning lake views and the serene atmosphere of this idyllic getaway, perfect for a relaxing vacation.brbr* Wake up to breathtaking views of Lake Simcoebr* Close to many attractions, including casino Rama, Many Restaurants br* Perfect for swimming, fishing, Kayaking and soaking up the sun.br* Enjoy a BBQ and cozy evenings around the fire pitbr* Enjoy bicycle riding, dart, board games, and Xbox games

Villa

Charming Cottage on Lake Simcoe

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$120.9

Enjoy your stay in a newly renovated, very clean, bright modern 1 bedroom apartment in downtown Orillia at a short distance to nearby amenities, restaurants, beaches, ski hills and shopping! Full kitchen stocked with the basic cooking supplies. You provide the groceries. Full sized fridge, stove, microwave and dishwasher. Onsite laundry -washer and dryer. We guaranty that you won't be disappointed . You can also enjoy our large backyard and if you wish , you can have BBQ.brbrI think that it should be mentioned that not only we take cleaning and disinfecting the place very seriously, but also that each apartment is self contained and doesn't have any air exchange with the others. The heating is not by furnace and air ducts in which case the same air circulates everywhere in the house. The heating is by modern hot water aluminum radiators separately for each apartment . The cooling is also by AC for each individual unit.brbrThe guest can use the apartment they have booked and the only shared space is the parking and the back yard.brbrWe are trying our best to help the guests to have enjoyable stay.

DaVel DeLuxe Sunrise

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$856.48

20 acres of private land, with a beautiful pond. We’ve had weddings, birthdays, corporate events, large family reunions and many more gatherings. A short drive from a few golf courses, Casino Rama, ski resorts and very close to several beaches.

Cottage

Stunning Private Cottage with beautiful Pond On 20 Acre Property

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$553.53

Enjoy a night soak in your private hot tub overlooking the peaceful canal. Roast smores in the firepit while listening to the beautiful sounds of nature. Take a walk across the road to the park and play with the kids. Let the dog run around the fully fenced backyard without worry. This home/cottage has ample room for everyone to spread out and enjoy a night in. With two separate livingrooms the kids can watch their favourite shows downstairs while the adults enjoy their own movie on the main floor. This raised bungalow has a fully stocked kitchen so you do not have to worry about running out of dishes before the dishwasher is full. It is in the city with neighbours on both sides and there is nothing but gorgeous nature and the canal behind you. Cozy beds and ample pillows and blankets makes for a great nights sleep. This place combines the ease and comforts of city life with the magical feeling of being out of the city. Do not forget your bug spray-you are on natures doorstep.

Orillia Oasis w/hot tub & canal-2 minutes from the beach!

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$157.84

The 4 season-charming cottage on Lake Simcoe is a beautiful getaway that offers stunning views of the water and is perfectly situated in a picturesque location, with breathtaking lake views and plenty of opportunities for outdoor recreation and relaxation. Just minutes from downtown Orillia, and minutes to all major shopping malls and stores, less than 10 minutes from Casino Rama. A 1.5-hour drive from Toronto.brbrBrand new 6 seats luxury hot tub just install in the cottage. You will enjoy the hot tub with the beautiful lake view.brbrRelax with the whole family at this peaceful lakeside retreat. With a beautiful outdoor space, bbq, firepit, kayak, with access to water, this cottage is spacious enough to provide its guest with comfort and joy. This Heritage waterfront-type cottage is suitable for family & friends.brEnjoy the beauty of the lake while experiencing the convenience and amenities of the Orillia area. brLots of local restaurants and shops nearby.brbrThe cottage is waterfront on Lake Simcoe and has 4 bedrooms, 2 washrooms, with a large parking spot. Living area with comfortable seating and a fireplace, a dining area, and a fully equipped kitchen. Bedrooms are cozy and comfortable, with warm bedding. with plenty of cozy seating areas and accessibility to all the necessities making it the best getaway location. We ask that you treat this cozy cottage as if it were your own, as we have high respect for our renters. brbrA patio faces the lake, with 6 seating and a barbecue grill for outdoor meals. The lake is perfect for swimming, boating, and fishing. The cottage has a private dock and 2 kayaks.br brThis beautiful lakefront house is close to parks, ski hills, and walking/cross-country ski trails.

Cottage

4 seasons waterfront cottage with hot tub on Lake Simcoe

Orillia, Ontario, Canada

4

Bed

Bath

8

Sleeps

$254.28

Relax with the whole family at this peaceful place to stay.brbrWelcome to the Stone House Farm!brbrWe have this beautiful property of 100 acres farm that we love but unfortunately, our lifestyle does not permit us to live there full time.brSo we would love to share with you our Retreat!brbrAt this time of the year, and with the snow coming, the property is perfect for outdoor activities:br- Snowshoeing… trails are indicated on the property.br- Cross-country skiingbr- Skating rink (we have a small pond on the property that we turn into)br- Also you can bring your ATV/snowmobile, and enjoy the ATV/snowmobile trails right beside the property! – we are not renting right now, only offering supervised tours.brbr20min away from Casino Ramabr30min away from Orillia br30min away from Lagoon Citybr

Country House

Stone Farm House - 3 bedrooms - private on 100 acres - 20 min from Casino Rama

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$156.5

Private Lakeside Bachelor Apartment in Downtown OrilliabrDiscover your perfect retreat! This fully separate bachelor apartment, with its own private entrance and bathroom, is nestled right on the shores of Lake Couchiching in the vibrant heart of downtown Orillia.brPrime Location:br• Steps from downtown shops, bars, pubs, and restaurantsbr• Walk to waterfront festivals, Tudhope Park, and grocery storesbr• Enjoy stunning lake views and easy access to the waterfrontbrStay where convenience meets charm!

Lakefront Living Downtown Orillia.

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$421.64

Situated on beautiful bass lake where your family vacation begins.brbrSit out under the stars and listen to beautiful bass lake. Enjoy a fire by the lakebrbrThis 3 bedroom 2 bathroom cottage is just 1hr 15 min from the GTA and is close to all amenities, but far enough away to relax

Cottage

Beautiful beachfront cottage on bass lake

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$455.08

Beautiful home, north end of Lake Simcoe, 1:10 min to GTA 4 min to downton Orillia. 5 bedrooms, 6 beds. 3.5 bathrooms.2 kitchens Up to8 people. Lots of privacy. Main floor and 2nd floor plus basement apartment are available for our VRBO guests. Entire home.brbrEnjoy gorgeous sunrise & sunset colors over the lake. Swans, Birds galour.brNew Hot tub. brPrivate dock, Double kayak, canoes and life jackets, ping pong, foosball table. Firepit, BBQbrAC, Gas Fireplace in comfy living room, dining rm, High speed unlimited Internet, cable & apps on a 50”screen TV, fully supplied kitchen, plus extra kitchenbrPrivate 3 decks, Five bedrooms four bathrooms brbrMaster with king bed and ensuite 3 pc. bathroom, balcony overlooks lake.brRoom with 1 double and single beds. Room with queen. Rooms overlook Lake Simcoe.brbrLarge driveway for 3-5 vehicles. brNature reserve on one side of property at the end of a cul-de-sac. Big yard for lots of activities.brHuge sandy beach and kids park at Tudhope Park 5 min drive or 3 min drive to boat launch. Lots of golf, biking, marinas, shopping, provincial parks all close by.brbrProperty is last house at the end of a cul-de-sac which makes it very large and private

Simcoe Waterfront Home with new Hot Tub ( near Casino Rama)

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$109.23

Large one bedroom apartment in a newly built addition to beautiful historic house. Only few minutes walk to downtown Orillia, the lakefront and the Marina. We have experience in hosting guests and would love to welcome you in our house. We know that your health and safety is of paramount importance, and we take extreeme measures to clean and disinfect the place as best as possible before and after every guest.brbrThe apartment is brand new, build and furnished to meet the highest standards, stainless steel appliances, washer and drier, Queen size bed and high end mattress. Despite being located on the main street, the apartment is facing the back yard with incredibly beautiful view and is very quiet. Large private deck allows you to relax and watch the birds and the squirrels chasing each other on the beautiful pine tree in front of you.brbrThe guests can use BBQ and the large back yard all the way down to our creek.brbrI think that it should be mentioned that not only we take cleaning and disinfecting the place very seriously, but also that each apartment is self contained and doesn't have any air exchange with the others. The heating is not by furnace and air ducts in which case the same air circulates everywhere in the house. The heating is by modern hot water aluminum radiators separately for each apartment . The cooling is also by AC for each individual unit.

DaVel DeLuxe Relaxation

Orillia, Ontario, Canada

Bed

Bath

2

Sleeps

$390.18

Welcome to your peaceful escape on the shores of Lake Simcoe in McPhee Bay. This waterfront retreat in Ramara offers the perfect blend of cozy indoor comfort and outdoor adventures — ideal for families, couples, or small groups.brbrThis newly renovated lakeside home is perfect for year-round escapes, whether you’re enjoying sunny summer days on the water or cozy winter weekends exploring nearby trails. Inside, the open-concept layout is bright and welcoming, with large windows that frame the views of McPhee Bay. With direct lake access, you`re just steps from swimming, paddling, or taking in peaceful sunsets in the warmer months—and in winter, it`s an ideal base for ice fishing, snowshoeing, or enjoying Orillia’s seasonal events.brbrOutdoor Space:brSpend summer days lounging on the spacious deck, complete with seating for 8 and a BBQ—perfect for evening dinners. The large, beautiful property offers a wide lakefront with an unobstructed, picturesque view of the lake and stunning sunsets. The lake is swimmable with a sandy bottom and stays around 3–5 feet deep for about 100 feet out, making it great for swimming, walking, or playing, whether you`re an adult or child. Outdoor games and plenty of seating are available for your enjoyment. brbrGuests have access to the entire backyard, lake, and the private dock (minus the garage adjacent from the house). brbrFor those who love water sports, the property is in McPhee Bay, the north end of Lake Simcoe, which is ideal for boating, canoeing, and fishing. Two marinas are in the bay. Marina Del Ray offers fishing boat, pontoon boat, and PWC rentals so you can easily take advantage of all the lake has to offer.brbrKitchen:brThe kitchen is fully equipped with all the essentials for preparing meals at home, including a full-size fridge, stove, oven, microwave, coffee maker, cookware, and utensils—perfect for everything from hearty winter breakfasts to summer BBQ sides. All you need to bring is Nespresso coffee pods, your preferred cooking oil, and seasonings!brbrBedrooms:brUpstairs, you’ll find two comfortable bedrooms, both with Queen beds. Both offer a lake view, making it the perfect wake-up spot. The home includes a full bathroom with a shower and a second half bathroom. Shampoo/conditioner is not supplied. Linens and basic toiletries are provided for your stay.brbrWhat’s Nearby:brbrFood & Drink:br- The Common Stove – Wood-fired dishes & cocktails (18 mins)br- Rustica Pizza Vino – Downtown Italian favourite (18 mins)br- Eclectic Café – Cozy café for coffee or brunch (18 mins)br- Webers Burgers – Famous roadside burgers (20 mins)brbrEssentials & Groceries:br- Ramara Fuels - Convenience store, gas, wood (2 min drive or 15 min walk)br- Zehrs Markets (17 mins)br- Costco Orillia (20 mins)br- Orillia Square Mall (15 mins)br- Downtown Orillia – Boutiques, cafés, and local finds (18 mins)brbrOutdoor Activities & Attractions:br- Marina Del Ray Marina (7 mins) - The marina is directly across the water from the cottage. Boat/jet ski/pontoon rentals are available at Lake Country Adventures Co. br- City operated Boat Launch (10 mins)br- Couchiching Beach Park – Beach, trails, and lakefront (19 mins)br- Tudhope Park – Biking, playgrounds & water access (20 mins)br- Casino Rama Resort (10 mins)br- Hardwood Ski and Bike – Winter cross-country trails (30 mins)br- Mount St. Louis Moonstone – Skiing & snowboarding (35 mins)br- Carden Alvar Provincial Park – Nature trails & birding (40 mins)brbrPlease note:br- Guest must be 25+ to bookbr- No pets allowed br- Firewood is not provided. Wood can be purchased at the nearby convenience storebr- We ask that you bring your own beach towels for outdoor use, thank you!br- A Ring camera is at the front entrance facing the driveway, and another is positioned at the back of the housebr- The home runs off well water that is purified but isn`t recommended for drinkingbr- The property`s landscaper is scheduled to conduct lawn maintenance bi-weekly on Mondays (weather permitting)br- We kindly ask that you review and respect the Renter’s Code of Conduct displayed inside the propertybrbrbrSTR LICENCE #2025.003

Lakeside Escape in Ramara | Private Water Access

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$119.45

Large one bedroom apartment in newly built addition to a beautiful historic house. Only few minutes walk to downtown Orillia, the lakefront and the Marina. We have experience in hosting guests and would love to welcome you in our house. We know that your health and safety is of paramount importance, and we take extreeme measures to clean and disinfect the place as best as possible before and after every guest.brbrThe apartment is brand new, built and furnished to meet the highest standards, stainless steel appliances, washer and drier, Queen size bed and high end mattress. Despite being located on the main street, the apartment is facing the back yard with incredibly beautiful view and is very quiet. Large private balcony allows you to relax and watch the birds and the squirrels chasing each other on the beautiful pine tree in front of you. I think that it should be mentioned that not only we take cleaning and disinfecting the place very seriously, but also that each apartment is self contained and doesn't have any air exchange with the others. The heating is not by furnace and air ducts in which case the same air circulates everywhere in the house. The heating is by modern hot water aluminum radiators separately for each apartment . The cooling is also by AC for each individual unit.brbrThe guest can use entire apartment they have booked and the only shared space is the parking and the back yard.

DaVel DeLuxe Sunsets

Orillia, Ontario, Canada

Bed

Bath

2

Sleeps

$344.09

Welcome to the Stone House Farm Retreat!brbrWe have 100 acres of gorgeous farm that we love, but, unfortunately our life-style does not permit us to live there full time.brSo, we would love to share with you our Retreat.brbrWelcome

Country House

Stone Farm House

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$113.56

Large one bedroom apartment in newly built addition to a beautiful historic house. Only few minutes walk to downtown Orillia, the lakefront and the Marina. We have experience in hosting guests and would love to welcome you in our house. We know that your health and safety is of paramount importance, and we take extreeme measures to clean and disinfect the place as best as possible before and after every guest.brbrbrThe apartment is brand new, build and furnished to meet the highest standards, stainless steel appliances, washer and drier, King size bed and high end mattress. Despite being located on the main street, the apartment is facing the back yard with incredibly beautiful view and is very quiet. Large private deck allows you to relax and watch the birds and the squirrels chasing each other on the beautiful pine tree in front of you.brbrWe will try our best to make your stay as enjoyable as possible.

DaVel DeLuxe Garden view

Orillia, Ontario, Canada

Bed

Bath

2

Sleeps

$91.17

Quiet location close to town amenities brPerfect for swimming boating fishing or watching the wildlife brFireplace to sit around at night brBbq to make you favourite meals brYou will love it so close to the lake

Lake front bachelor Close to all amenities casino Rama Ski hills

Orillia, Ontario, Canada

Bed

Bath

Sleeps

$63.58

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 custom kitchen, a full bathroom, air conditioning, Dishwasher, Washer/Dryer, Wifi & a brand new smart TV with all the popular streaming apps. Netflix and Amazon Prime included.brbrThere is a queen size bed with under bed storage and a closet. There is a pull-out sofa in the living room.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

Home away from home in Orillia

Orillia, Ontario, Canada

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Bath