Vacation rentals with a kayak in York Region

4.98 out of 5 average rating, 53 reviews

Cottage in Innisfil

The Gingerbread House | Near Lake + Wedding Venues

This peaceful 3-bedroom cottage combines rustic charm with modern comforts. The open-concept main floor features hardwood floors, a cozy living area with a wood-burning stove, and tons of natural light. The fully stocked kitchen makes cooking easy, and a backyard deck with BBQ is perfect for relaxing after a day by the lake. Fast Wi-Fi and a dedicated desk make it ideal for remote work or school. Whether you’re here for a wedding, a family getaway, or a quiet recharge, you’ll feel right at home.

Superhost

Guesthouse in Innisfil

4.88 out of 5 average rating, 24 reviews

Luxury Stay In Innisfil!

Luxury Stay in Innisfil! Stay in our renovated 1 bedroom + 1 lower level unit. Offering a private entrance, spacious layout with a large primary room + a den/living room + dinette accommodating up to 4 guest. Primary bedroom offers a KING Sized bed, large front facing windows with lots of natural light, walk-in Closet and a private ensuite! Located in the heart of Innisfil, your family will be close to everything when you stay with us. Walking distance to shops, restaurants and INNSIFIL BEACH!

Superhost

Cottage in Georgina

4.87 out of 5 average rating, 160 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

4.86 out of 5 average rating, 22 reviews

Enjoy your stay at a cozy One bedroom apartment!

Modern. This brand new 1 bedroom condo is located less than an hour north of Toronto, at the Friday Harbour All Seasons Resort, Innisfil, ON. This resort community infuses fun with relaxation. Your getaway features activities, golf course, nature preserve & trails, waterfront beach, boating, canoeing, biking & more.As an all-season resort, there is plenty to do all year round, and Harbour Fest at the Pier has plenty of live music, family entertainment and tasty treats -weekends, all summer long

4.85 out of 5 average rating, 188 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina while lounging or eating outside.

4.96 out of 5 average rating, 116 reviews

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

5 out of 5 average rating, 166 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

4.99 out of 5 average rating, 165 reviews

Cottage in Georgina

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

4.93 out of 5 average rating, 184 reviews

The Friday Flat | Sunny Escape by the Marina

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

4.91 out of 5 average rating, 281 reviews

Home in Georgina

Luxury Lakefront Hot Tub Private Beach Lake Simcoe

✨Perfect Family & Friends Getaway on Lake Simcoe Escape to a luxury Lake Simcoe waterfront retreat with private sandy beach, hot tub under the stars, kayaks, SUP, lily pad, and kids’ sand play area. Enjoy a lakeview open kitchen, 14-seat dining table, 3 family rooms with fireplaces, and a game room. Outdoors: firepit with Muskoka chairs, gazebo with sofas, and west-facing sunsets. Perfect for Christmas gatherings, ice fishing trips, or group getaways year-round.

4.94 out of 5 average rating, 163 reviews

Cottage in Richmond Hill

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco