10 Best Orillia Apartments on Holiday Lettings - Condos

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66 Vacation rentals

10

Vacation home rental

Ontario / Orillia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
My home is a beautiful big place with lots of character. It has high vaulted ceilings with skylights. My home backs into the forest which is for me the best part as you can enjoy your coffee in the morning on the covered porch rain or shine. You can see squirrels, birds …see more

from $151 / night

$755 / week

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from $151 / night

5

Orillia Vacation home rental

Ontario / Orillia

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden
Once you arrive at my home, I will show you around, provide a key, and show you your bedroom and bath. You are welcome to come and go as you please and I will provide you with a key. There is complimentary coffee and tea and you are welcome to use the kitchen. Your …see more

from $42 / night

$227 - $306 / week

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from $42 / night

7

Vacation guest house rental

Ontario / Orillia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
This lakeside guest house with loft is ideal for a romantic getaway or family fun on the water. For the adventurous, there are many provincial parks for fishing with hiking trails and cycling trails at Bass Lake, McRae Provincial Park and Mara Point. For those with a bo …see more

from $129 / night

$755 / week

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from $129 / night

(1) Excellent 

12

Orillia Vacation cottage rental

Ontario / Orillia

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Our four bedroom two bathroom cottage would be great for a family reunion or a shared vacation with another family. With six beds the cottage comfortably sleeps eight people. The outside prperty is ideal for summer swimming and boating. There is a large dock that …see more

from $209 / night

$1,062 / week

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from $209 / night

(2) Excellent 

35

Vacation cottage in Orillia

Ontario / Orillia

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Leaning Tree Cottage is located directly on the water with private dock and Sandy beach on Crystal clear Lake Couchiching. We are on the West side of the Lake, just north of the Weber's Hamburger restaurant on Highway 11. The water is waist deep for 200+ feet out and …see more

from $151 / night

$1,207 - $1,660 / week

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Responds fast!
avg. 3 hours 51 minutes

from $151 / night

(1) Good 

22

Vacation cottage in Orillia

Ontario / Orillia

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 5 mi
  • Child friendly
Just an hour and a half drive from Toronto, the Redwood Retreat is a well maintained and welcoming waterfront cottage situated on the north shores of Lake Simcoe with easy access to downtown Orillia and Casino Rama. Whether it is lazy days in the sun while taking occasi …see more

from $138 / night

$963 - $1,430 / week

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from $138 / night

(1) Very Good 

6

Orillia Vacation cottage rental

Ontario / Orillia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Whispering Pines Cottage is rated as a 5* VACATION PROPERTY on Trip Advisor and is one of Flip Key's most popular locations. Owners have just had a change of plans and their beautiful cottage is available from June 1st onwards. Please note that there are no pets allo …see more

from $314 / night

$2,199 / week

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Responds fast!
avg. 3 hours 50 minutes

from $314 / night

7

Ski home to rent in Orillia

Ontario / Orillia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Being built in 2017 and ready for occupancy by May 2018, this seven bedroom lakeside home has everything you could possibly want for your vacation! Photos to come as the project evolves! Perfect for families. Serenity  is located on Lake Simcoe just an hour and a …see more

from $755 / night

$5,584 / week

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Responds fast!
avg. 14 minutes

from $755 / night

(2) Excellent 

17

Vacation cottage in Orillia

Ontario / Orillia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Hi Everyone We are small informal resort with twenty-two 1,2,3,4 Bedroom self catering cottages with private bathrooms 4 bedroom 4 star (4 pc bathroom,large-very specious living room,3 single 3 double beds, sleeps max 9 people) 3 bedroom 4 star (4pc bathroom,large-very …see more

from $135 / night

$500 / week

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from $135 / night

51

Ski cottage to rent in Orillia

Ontario / Orillia

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Sometimes with persistence and luck you find a gem for your family vacation in the beauty & convenience of Lake Simcoe and this generously sized 6000 sq ft brand new lakefront home is the place to look! Golf, swim and sail in summer, cross country and downhill skiing in …see more

from $753 / night

$5,266 / week

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Responds fast!
avg. 14 minutes

from $753 / night

36

Ski home to rent in Orillia

Ontario / Orillia

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Searching for the perfect Lake Simcoe cottage rental? This gorgeous newly built 6+ bedroom home offers you all the wonders of lake living without compromising on luxury. Located on the western shores of Lake Simcoe,  just 15 minutes to Orillia with it's Saturday morning …see more

from $453 / night

$3,169 - $5,282 / week

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avg. 14 minutes

from $453 / night