Condo holiday rentals in Simcoe County
Find and book unique condos on Airbnb
Top-rated condo rentals in Simcoe County
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Simcoe County condo rentals
Weekly condo rentals
Condo in Innisfil
4.82 out of 5 average rating, 223 reviews1 bdrm/1 bath oasis at FH Resort in Innisfil
7–14 Aug
Condo in The Blue Mountains
4.89 out of 5 average rating, 350 reviewsBase of Blue Mountain, Modern Updated Studio
7–14 Sep
Condo in Innisfil
4.86 out of 5 average rating, 124 reviewsFriday Harbour Resort Penthouse Lake Simco
24 Feb – 3 Mar
Condo in The Blue Mountains
4.82 out of 5 average rating, 201 reviewsHillside Lookout - Walk to Blue - Sleeps 6
12–19 Sep
Condo in Innisfil
4.95 out of 5 average rating, 183 reviewsDesigner Condo with beautiful harbour view.
11–18 Sep
Condo in Innisfil
4.97 out of 5 average rating, 146 reviewsStylish getaway condo, resort living
1–8 Jul
Condo in The Blue Mountains
4.97 out of 5 average rating, 116 reviewsRustic Chic Renovated 2Bd Condo by Village
3–10 May
Condo in The Blue Mountains
4.95 out of 5 average rating, 713 reviewsBlue Mountain Village| Stunning Mountain Views
10–17 Oct
Pet-friendly condo rentals
Condo in The Blue Mountains
4.9 out of 5 average rating, 371 reviewsSpring Getaway | Blue Mountain
6–13 Jun
Condo in The Blue Mountains
4.89 out of 5 average rating, 114 reviewsPet friendly, ground floor condo, steps to Village
24–31 May
Condo in The Blue Mountains
4.82 out of 5 average rating, 520 reviewsCreekside Smart Studio at Blue Mountain
24 Sep – 1 Oct
Condo in Oro
4.94 out of 5 average rating, 34 reviewsCozy 1-Bedroom Romantic Retreat with full Kitchen
12–19 Nov
Condo in Shanty Bay
4.73 out of 5 average rating, 15 reviewsLux Studio in Horseshoe Valley
27 Aug – 3 Sep
Condo in Oro
4.95 out of 5 average rating, 78 reviewsPet-friendly, 1 BR condo in Horseshoe Valley
5–12 Feb
Condo in Barrie
4.93 out of 5 average rating, 89 reviewsBright MCM 2 Bedroom Walk Up with Private Deck/BBQ
28 Sep – 5 Oct
Condo in Oro-Medonte
4.89 out of 5 average rating, 64 reviewsLovely condo unit in Horseshoe Valley
4–11 Jun
Condo rentals with a pool
Condo in The Blue Mountains
4.94 out of 5 average rating, 175 reviewsThe Blue Mountain's Dream Escape (Rivergrass)
1–8 Jun
Condo in The Blue Mountains
4.92 out of 5 average rating, 404 reviews★Blue Mountain Village★ Cozy, Stylish, 360 Views
27 Oct – 3 Nov
Condo in The Blue Mountains
4.97 out of 5 average rating, 126 reviewsSnowbridge Escape at Blue
3–10 Jan
Condo in Blue Mountains
4.91 out of 5 average rating, 264 reviews2 Bedroom, 2 Level Condo on Blue Mountain!
29 Dec – 5 Jan
Condo in The Blue Mountains
4.94 out of 5 average rating, 159 reviewsBlue Mountain condo in Historic Snowbridge
3–10 Aug
Condo in The Blue Mountains
4.94 out of 5 average rating, 180 reviewsThe Rustic Retreat - Walk to Blue / Outdoor Pool
28 Sep – 5 Oct
Condo in The Blue Mountains
4.88 out of 5 average rating, 188 reviewsHidden Haven - Shuttle to Blue / Outdoor Pool
26 Aug – 2 Sep
Condo in The Blue Mountains
4.93 out of 5 average rating, 143 reviewsMountainside Studio Bliss: Just Renovated, Tennis
7–14 Mar
Destinations to explore
- Condo rentals Toronto
- Condo rentals Canada
- Condo rentals Ontario
- Condo rentals Downtown Toronto
- Condo rentals Mississauga
- Bed and breakfasts Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Boutique hotel rentals Simcoe County
- Rentals with a sauna Simcoe County
- Family-friendly rentals Simcoe County
- Rentals with a kayak Simcoe County
- Rentals with outdoor seating Simcoe County
- Rentals with a washing machine and dryer Simcoe County
- Rentals with lake access Simcoe County
- Rentals with a hot tub Simcoe County
- Smoking-friendly rentals Simcoe County
- Bungalow rentals Simcoe County
- Loft rentals Simcoe County
- Pet-friendly rentals Simcoe County
- House rentals Simcoe County
- Chalet rentals Simcoe County
- Monthly Rentals Simcoe County
- Villa rentals Simcoe County
- Waterfront rentals Simcoe County
- Farmstay rentals Simcoe County
- Rentals with beach access Simcoe County
- Cabin rentals Simcoe County
- Apartment rentals Simcoe County
- Beachfront rentals Simcoe County
- Rentals with a fire pit Simcoe County
- Rentals with an EV charger Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with pools Simcoe County
- Private suite rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Kid-friendly rentals Simcoe County
- Hotel rentals Simcoe County
- Rentals with breakfast Simcoe County
- Cottage rentals Simcoe County
- Guesthouse rentals Simcoe County
- Rentals with a patio Simcoe County
- Townhouse rentals Simcoe County
- Tiny house rentals Simcoe County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom