Holiday rentals with a kayak in Greater Toronto and Hamilton Area

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!

Romantic & Cozy Countryside luxury loft with views

Romance in the Country. Getaway from the hustle with your sweetheart, to play, rest/work stay-cation. Newly built, full kitchen, bath/laundry/EV charger. Great trails, theatre, shopping in quaint downtown Port Perry, boating, golfing, equestrian farm, museums, & amazing 5 star restaurnts in Port Perry. Enjoy the pond on the property & lots of places to enjoy peace & quiet together! Ask about our Chef and Pontoon experiences. 1 hr from TO, 8 min to Port Perry. We have 2 rms queen loft/king.

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!

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.

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

Niagara Dreamhouse on the Lake|Private Sandy Beach

STR-004-2025 Enjoy the 180-degree view of Sunrise and Sunset of Lake Erie from the living room. Great place to stay when you visit Niagara Region Close to Long beach area. Our Clean and lovely 2-bedroom house with a fully equipped kitchen, large indoor living area, high-speed internet. Perfect Weekend getaway from the city life with family and friends. Watch your children build sandcastle, paddle a kaya on the blue water, create memories, funs and relax on the clean private sandy beach.

Luxury 3BR Sky Condo - Award Winning Design

- Rated one of the best in the city with direct underground path to Union Station, the shopping mall, grocery store, LCBO, & Scotiabank Arena - This condo offers luxurious living on the 63rd floor with stunning views of the lake, Porter Airport, & everything iconic about Toronto - Indulge in vibrant nightlife, major league games, conferences & concerts, or just cozy up by the fireplace - Dedicated office space - Spacious bedrooms with gorgeous views of the city and lake

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

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.