House holiday rentals in Simcoe County
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Top-rated house rentals in Simcoe County
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Simcoe County house rentals
House rentals with a pool
Home in The Blue Mountains
4.95 out of 5 average rating, 148 reviewsSerene mountainside home View/Shuttle Bus/Pool
9–16 Oct
Home in The Blue Mountains
4.92 out of 5 average rating, 166 reviewsViews Mountains Sauna/Shuttle/Pool/Entertainment
15–22 Jul
Home in Collingwood
4.84 out of 5 average rating, 32 reviewsBatteaux Chalet - Pool + Blue Mountain Skiing
22–29 Sep
Home in Collingwood
5.0 out of 5 average rating, 23 reviewsAn oasis getaway near trails, lake, restaurants
27 May – 3 Jun
Home in Barrie
4.91 out of 5 average rating, 46 reviewsLuxurious 4BDRM-King Bed-Barrie-fire pit
16–23 Jan
Home in Innisfil
5.0 out of 5 average rating, 18 reviewsWaterfront home, sauna, jacuzzi & Heated pool
11–18 Dec
Home in Honeywood
4.98 out of 5 average rating, 50 reviewsSunnylea Acres
5–12 Nov
Home in Newmarket
5.0 out of 5 average rating, 7 reviewsBeautiful Pond View stay!
19–26 Dec
Weekly house rentals
Home in Bradford West Gwillimbury
4.97 out of 5 average rating, 35 reviewsGuest Suite In Bradford West Gwillimbury
9–16 Oct
Home in Collingwood
4.91 out of 5 average rating, 22 reviewsBlue Mountain Home
19–26 Sep
Home in Minesing
5.0 out of 5 average rating, 22 reviews4br 4bth home 10min to Golf/Ski resorts+waterfront
7–14 Apr
Home in Barrie
4.85 out of 5 average rating, 26 reviewsCozy Basement 4 minutes to Centennial beach Barrie
25 Jul – 1 Aug
Home in Collingwood
4.94 out of 5 average rating, 79 reviewsPrivate, brand-new 1 bdrm unit
31 May – 7 Jun
Home in Barrie
5.0 out of 5 average rating, 11 reviewsSuite St. Vincent
3–10 May
Home in Midland
5.0 out of 5 average rating, 42 reviewsHistoric Coach House hosted by John & Donna
2–9 Jul
Home in Moonstone
5.0 out of 5 average rating, 11 reviewsSki Cabin Bliss; Cozy Retreat
13–20 Jun
Private house rentals
Home in Tiny
5.0 out of 5 average rating, 3 reviewsGrandview Family Beach House w/ Hot Tub & Sauna
9–16 Sep
Home in Barrie
4.96 out of 5 average rating, 70 reviewsModern 5-bedroom house close to Ardagh Bluffs
6–13 Jan
Home in Gravenhurst
5.0 out of 5 average rating, 25 reviewsSunfilled cottage on the lake
28 Mar – 4 Apr
Home in Barrie
4.82 out of 5 average rating, 60 reviewsCheerful 4 Bedroom Home with Indoor Fireplace
1–8 Feb
Home in Barrie
4.98 out of 5 average rating, 86 reviewsWaterfront home, city/sunset view & steps to beach
3–10 Dec
Home in Barrie
4.97 out of 5 average rating, 31 reviewsExclusive Lakefront House on Private Lake
5–12 Jul
Home in East Gwillimbury
5.0 out of 5 average rating, 6 reviewsBest cozy place near the lake.
21–28 May
Home in Shelburne
5.0 out of 5 average rating, 15 reviewsTranquil 2BR Triplex in the Heart of Shelburne
15–22 Sep
Destinations to explore
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