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Simcoe Island Holiday Rentals

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Our top choices for Simcoe Island holiday rentals

1. Dwell Aparthotels

Dwell Aparthotels
4.0 star property
Downtown Kingston
9.6 out of 10, Exceptional, (62 reviews)
"Great location. Very clean and welcoming"
Canada
Karen
The price is AU$382
includes taxes & fees
10 Nov - 11 Nov
Dwell Aparthotels

2. Historic Portsmouth Village - Modern Comfort

Historic Portsmouth Village - Modern Comfort
Portsmouth
The price is AU$145
includes taxes & fees
3 Nov - 4 Nov
Historic Portsmouth Village - Modern Comfort

3. Cozy Home Away from Home

Cozy Home Away from Home
Kingston
9.0 out of 10, Wonderful, (28 reviews)
"Close to everything, clean, comfortable, accommodating host, very good value, would stay again "
Canada
David
The price is AU$191
includes taxes & fees
28 Oct - 29 Oct
Cozy Home Away from Home

4. Cozy Countryside Suite

Cozy Countryside Suite
Loyalist
The price is AU$228
includes taxes & fees
16 Oct - 17 Oct
Cozy Countryside Suite

5. The Art Studio | free parking

The Art Studio | free parking
Downtown Kingston
10.0 out of 10, Exceptional, (8 reviews)
"The place was warm, cozy and inviting. Loved it. The hosts were also so lovely to deal with, Great price, great location. Perfect!"
Canada
kelli t.
The price is AU$220
includes taxes & fees
25 Oct - 26 Oct
The Art Studio | free parking

6. Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!

Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!
Kingston
9.2 out of 10, Wonderful, (5 reviews)
"The instructions were simple but clear. Everything was clean, nice place."
Canada
Marco
The price is AU$397
includes taxes & fees
10 Nov - 11 Nov
Cozy, Quiet Home in Kingston. Short drive to Queen's University. Pet Friendly!

7. Cozy home on a quiet street minutes to downtown Kingston!

Cozy home on a quiet street minutes to downtown Kingston!
Rideau Heights
10.0 out of 10, Exceptional, (10 reviews)
"It clean Well maintained Owner alway available to respect your questions."
Canada
Olivia C.
The price is AU$372
includes taxes & fees
4 Nov - 5 Nov
Cozy home on a quiet street minutes to downtown Kingston!

8. Cozy downtown one bedroom free parking

Cozy downtown one bedroom free parking
Sunnyside
6.2 out of 10, (14 reviews)
"A nice cozy place perfectly situated in Kingston"
Canada
Brad G.
The price is AU$220
includes taxes & fees
19 Oct - 20 Oct
Cozy downtown one bedroom free parking

9. Prime Location Duo Nest & Rest

Prime Location Duo Nest & Rest
Rideau Heights
7.6 out of 10, Good, (35 reviews)
"Very nice and convenient stay"
Canada
Terry
The price is AU$259
includes taxes & fees
19 Oct - 20 Oct
Prime Location Duo Nest & Rest

10. The Neighbourhood: Expansive loft | free parking

The Neighbourhood: Expansive loft | free parking
Downtown Kingston
10.0 out of 10, Exceptional, (1 review)
"Beautiful apartment decorated by an artist, I’m sure. Walking distance to downtown. Lovely and warm even though it was snowing. Host are super friendly and helpful. "
United Kingdom
Elspeth C.
The price is AU$266
includes taxes & fees
18 Oct - 19 Oct
The Neighbourhood: Expansive loft | free parking

11. Spacious Historic Downtown Stableman`s House Loft

Spacious Historic Downtown Stableman`s House Loft
Downtown Kingston
10.0 out of 10, Exceptional, (11 reviews)
"Great place, convenient location too!"
United States
Michael D.
The price is AU$306
includes taxes & fees
25 Oct - 26 Oct
Spacious Historic Downtown Stableman`s House Loft

12. Charming historic 2-bedroom coachhouse in Kingston

Charming historic 2-bedroom coachhouse in Kingston
Downtown Kingston
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property with obvious attention paid to the details of traveling needs. Host very prompt to respond to questions. Great location."
United States
Susan
The price is AU$416
includes taxes & fees
19 Oct - 20 Oct
Charming historic 2-bedroom coachhouse in Kingston

13. Beautiful house right by Portsmouth Olympic Harbour.

Beautiful house right by Portsmouth Olympic Harbour.
Portsmouth
9.6 out of 10, Exceptional, (5 reviews)
"It is a great house with all possible necessities..I would definitely here again!"
United States
margaryta y.
The price is AU$322
includes taxes & fees
2 Nov - 3 Nov
Beautiful house right by Portsmouth Olympic Harbour.

14. 18th Century Luxury Suite with Rustic Charm

18th Century Luxury Suite with Rustic Charm
KIngston
10.0 out of 10, Exceptional, (1 review)
"Great place. Great location. Lots of room. Clean. Maybe a few more steps than two 77 year olds would normally want. But still worth it!!! "
United States
thomas h.
The price is AU$261
includes taxes & fees
10 Nov - 11 Nov
18th Century Luxury Suite with Rustic Charm

15. Happy House | Free Parking | Downtown

Happy House | Free Parking | Downtown
Downtown Kingston
10.0 out of 10, Exceptional, (11 reviews)
"We loved this house and had a great stay - very cosy house with great amenities "
Canada
Julia B.
The price is AU$368
includes taxes & fees
2 Nov - 3 Nov
Happy House | Free Parking | Downtown

16. Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!

Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!
Calvin Park
6.0 out of 10, (11 reviews)
"Very great!"
Canada
Fiona
The price is AU$430
includes taxes & fees
20 Oct - 21 Oct
Charming Kingston Home w/Private Yard & Peaceful Vibes — Family Friendly!

17. Beautiful 3-bedroom bed & breakfast in wonderful Kingston location

Beautiful 3-bedroom bed & breakfast in wonderful Kingston location
Rideau Heights
The price is AU$567
includes taxes & fees
28 Oct - 29 Oct
Beautiful 3-bedroom bed & breakfast in wonderful Kingston location

18. Kingston Lodge: Comfy & Cozy w/ Natural Scenery

Kingston Lodge: Comfy & Cozy w/ Natural Scenery
Bayridge West
8.8 out of 10, Excellent, (6 reviews)
"Great space. A perfect layout."
United States
Joe W.
The price is AU$257
includes taxes & fees
10 Nov - 11 Nov
Kingston Lodge: Comfy & Cozy w/ Natural Scenery

19. Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)

Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)
Kingston
8.4 out of 10, Very good, (9 reviews)
"Family friendly, we were a family of 8 and it met all our needs."
Canada
Judy
The price is AU$538
includes taxes & fees
10 Nov - 11 Nov
Big & Charming Bungalow Getaway (nearby Walmart, LCBO, Beer Store, Mall, etc.)

20. Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds

Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds
Kingston
9.6 out of 10, Exceptional, (25 reviews)
"Was a really pleasant stay :)"
Canada
Eric
The price is AU$916
includes taxes & fees
22 Oct - 23 Oct
Arbour Ridge Vacation Home - Trail View! 5 bedrooms, 7 beds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Simcoe Island Hotel Reviews

Find out more about Simcoe Island

Everything you need to know about Simcoe Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Simcoe Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe Island holiday rentals we have selected for you start as low as AU$259 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Simcoe Island rentals

At Expedia, we put the best Simcoe Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simcoe Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.