Condo vacation rentals in Simcoe County

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Top-rated condo rentals in Simcoe County

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Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake. Come experience the ultimate waterfront getaway at Friday Harbour!

Oct 11 – 18

G$22,724 GYD per night

Guest favorite

Condo in The Blue Mountains

4.92 out of 5 average rating, 246 reviews

Cozy Studio Mountainside stay in Blue Mountains

Summer and Spring are the perfect time to visit Blue. This cozy STUDIO ground floor condo is perfect for a couple or small family (Max 4). The unit includes: a comfy queen bed and a pop up sofa bed, bathroom with jacuzzi tub, electric fireplace and full kitchen with everything you need. Free parking. Two shared hot tubs (open daily) and tennis courts. Easy access to for hiking trails. Pool opens in May. The Blue Village is only a 5 minute drive away with great restaurants and shops.

May 2 – 9

G$15,615 GYD per night

Guest favorite

Condo in Collingwood

4.92 out of 5 average rating, 169 reviews

Lovely Condo Near Lake Beach Spa Village *King Bed

Feel at home in this Cozy, Bright and Spacious One Bedroom Condominium Suite with European Touch of Living Style. Fully furnished and Equipped *King Bed and Single Bed *Free Daily Access to Beach at Provincial Park *In Suite Washer/Dryer *Free Assigned Parking LOCATED in Cranberry Village next to Living Stone Hotel. - 3 mins walk to On-Side Restaurants, Bar, Café, Bakery, Trails - 10 mins drive to BM Village, Spa, Scenic Caves, Golf Courses, Tennis Courts - 5 mins drive to Lake and Beach

Sep 28 – Oct 5

G$26,147 GYD per night

Guest favorite

Condo in Oro

4.88 out of 5 average rating, 118 reviews

4-Bed Country Club Haven with Pool, BBQs, and More

Welcome to our one-of-a-kind 4-bed condo country club, an exceptional destination that caters to large families and offers an unforgettable vacation experience. This uniquely structured property features two separate bedroom suites, with Wi-Fi and a range of outstanding amenities, your every need will be catered to. Dive into the ultimate aquatic experience with our heated indoor/outdoor pool, indulge in the benefits of our sauna, and melt away your cares in the inviting hot tub.

Nov 13 – 20

G$29,938 GYD per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 106 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

Jul 10 – 17

G$17,361 GYD per night

Superhost

Condo in Innisfil

4.86 out of 5 average rating, 106 reviews

Beautiful 1 Bed/1Bath- Friday Harbour Resort

Enjoy our 4th floor modern condo to yourself! This 1 bedroom, 1 bathroom condo is located at the luxury all season, Friday Harbour Resort in Innisfil Ontario. Our fully furnished unit features a king bed, pullout couch, a large west facing balcony with barbeque and beautiful sunsets! Experience the 4 season recreation environment provided by the resort. There is a grocery store, Starbucks, LCBO, restaurants and entertainment steps away on the boardwalk! Fun for all!

May 21 – 28

G$18,499 GYD per night

Guest favorite

Condo in Barrie

4.81 out of 5 average rating, 123 reviews

Newly renovated 1 bedroom condo with free parking

Enjoy staying in this stylish and cozy, newly renovated condo. Situated close to the many amenities Barrie and surrounding area has to offer! Enjoy parks, hit the trails, ski hills or head to the beach within minutes Easy access to the 400, Close to shopping, spas, many restaurants and the beautiful downtown waterfront area. Location will not disappoint. Main level with a walk out patio and fireplace. Equipped with a smart tv and Netflix for those cozy nights in.

Feb 9 – 16

G$20,600 GYD per night

Guest favorite

Condo in Oro

4.9 out of 5 average rating, 154 reviews

Spacious 1-br w pool & jacuzzi at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Oct 19 – 26

G$20,678 GYD per night

Superhost

Condo in Innisfil

4.8 out of 5 average rating, 107 reviews

Friday Harbor Resort Getaway

Brand new, modern, bright, luxurious, fully furnished 1 bedroom condo with a large, patio-like balcony located in the beautiful Friday Harbour All Seasons Resort. Your perfect getaway features activities, golf course, nature preserve & trails, waterfront beach, boating, restaurants, and more. Queen bed, sofa bed, One Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking private pool. 1 Free Parking Spot, Electric BBQ, In-Suite Laundry.

Jun 9 – 16

G$25,261 GYD per night

Guest favorite

Condo in Collingwood

4.99 out of 5 average rating, 107 reviews

K's Cozy Condo -Minutes from Lake, Trails, Shops

Make yourself at home at this quiet bright end unit condo! Your home away from home in Cranberry Village- walking distance to a bar, restaurant & café and just minutes from Blue Mountain, Scandinave Spa & Downtown Collingwood shops & restaurants. Great for family vacations, romantic getaways or business travelers! Free Parking, in unit washer & dryer, WiFi & 2 TVs. We are committed to providing a safe and comfortable space for our guests.

Nov 1 – 8

G$36,488 GYD per night

Guest favorite

Condo in Collingwood

4.94 out of 5 average rating, 591 reviews

Modern & Chic Sanctuary Suite in Collingwood

Unit located by Living Stone Golf Resort, minutes away from downtown Collingwood, and 10 mins from Blue Mountain/Scandinave Spa. Our renovated condo offers modern-chic elegance. Enjoy 625 sq ft of privacy with two bedrooms and one bathroom with tub and shower. There is also a sofa, electric fireplace, Netflix and basic cable, WIFI, en-suite washer-dryer. Outdoor terrace with garden views.

Sep 21 – 28

G$23,417 GYD per night

Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 111 reviews

Lake Simcoe Resort Retreat

Beautiful, fully furnished one bedroom vacation retreat in the vibrant resort community of Friday Harbour. Experience the all-season recreation including the beach, marina, nature preserve, eighteen hole golf course, sports facilities and more! Find everything you're looking for, from grocery stores and restaurants to coffee shops and the LCBO, just steps from the boardwalk.

Nov 12 – 19

G$26,291 GYD per night