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Holiday rentals in Simcoe County

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Holiday rentals for every style

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Popular amenities for Simcoe County holiday rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Other great holiday rentals in Simcoe County

Guest favourite
Cabin in Severn Bridge
4.89 out of 5 average rating, 38 reviews

Oak Cabin on Sparrow Lake

KimberlyRating, 5 stars1 week ago
The place had everything we needed—clean, peaceful, and filled with activities, especially fishing, which we really enjoyed. We were also so happy to spot river otters during our stay! Big thanks to Ash and Nicholas for being so accommodating with our inquiries. We just got home and are already wishing we could go back!
Top guest favourite
Home in Georgian Bay
4.99 out of 5 average rating, 86 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

BecciRating, 5 stars3 weeks ago
We had a wonderful time celebrating our friend’s bachelorette. We’ll definitely have to come back one day when it’s a little warmer!
Guest favourite
Flat in Midland
4.91 out of 5 average rating, 95 reviews

Loft By The Bay

DavidRating, 5 stars1 week ago
This was my wife and I’s second time visiting Midland to attend the annual butter tart festival. Our previous rental unit last year was great as were the furnishing so the bar was high for this year’s Airbnb rental. In fact, the “Home in Midland” rental unit and the hosts exceeded our expectations. The rental unit's location was only minutes from the festival and most amenities such restaurants, waterfront and stores. We never moved the car during our stay since everything was within a short walk. About the hosts welcoming attitude and hospitality: Upon arrival, we requested an early entry which was granted without hesitation. We were also fortunate enough to meet one of the hosts (Shelby) she was extremely pleasant and assisted us in making sure we were in the right parking spot, which was well indicated. We walked up 2 flights of stairs to get to our unit and were pleasantly surprised at the space of the rental . The pictures online were absolutely on point and matched expectations.
Top guest favourite
Flat in Innisfil
5 out of 5 average rating, 77 reviews

Spacious Apartment 5 Minute Walk to Innisfil Beach

LindsayRating, 5 stars1 week ago
This has been hands down the best Airbnb we have ever stayed at. Dawn and Rob have truly thought of everything to make the space feel like home! They were very quick to respond to questions and had great recommendations for the area. The entire place was well stocked with everything you could think of including board games, cookware and much more. We will definitely be back!
Superhost
Tent in New Tecumseth
5 out of 5 average rating, 4 reviews

The Frog’s Lilypad

CamilleRating, 5 stars8 months ago
We had a wonderfully relaxing stay at Melanie's Frog Pond tent. Melanie is friendly and kindly welcomed us with a basket of goodies. The grounds are beautiful and peaceful, as well as the tent and amenities. The spa was amazing and definitely a highlight for us! Both the sauna and hot tub are wood fired which creates a cozy environment with the cute little chimneys. The bed in the tent is heated for chilly nights and it's so comfy, we had excellent deep sleeps. We went for a great hike just a 5 minute drive away. There is lots to do on the grounds as well, we enjoyed the pool table, fire pit, and BBQ. There were plenty more activities but we were having such great time chilling in the spa we didn't get around to the other games that were available. We were lucky enough to have the whole place to ourselves, would definitely return us two or it would be really fun with a group as well! Thanks Melanie :-)
Guest favourite
Cottage in Innisfil
4.92 out of 5 average rating, 39 reviews

Lakefront Luxury with Private Dock

RobinRating, 5 stars2 months ago
This place is extraordinary! Beautiful space to be in with a great bit of lake to enjoy. Would highly recommend, and hope to return myself some day.
Guest favourite
Tiny home in Uxbridge
4.9 out of 5 average rating, 97 reviews

The Cozy Coop - Tiny Cottage

RachelRating, 5 stars1 week ago
I stayed for 2 nights in this tiny home and it was the perfect get away. The fire outside was nice to just sit around as well as the inside being so neat and tidy! Was an amazing property with many walking trails around which with great! Would definitely go up again!!
Flat in Barrie
4.83 out of 5 average rating, 54 reviews

1 bed apt Downtown. walking distance to beach

OliviaRating, 5 stars4 weeks ago
Nice place, very walkable area!
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