Waterfront holiday rentals in Simcoe County

Cozy Stays – Your Fall Getaway at Friday Harbour

Welcome to our exquisite 2BR/2BA oasis, where relaxation knows no bounds. Embrace the tranquility of our inviting space. Indulge in the comforts of home with a fully equipped kitchen, cozy living area and two private bedrooms designed for restful nights. Soak in the hot tub's warmth, swim and lounge by the pool or gather round the fire pit for memorable conversations under the stars. Your perfect vacation retreat awaits. Book now to experience luxury, comfort & outdoor delight like never before!

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private 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! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

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

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

Friday Harbour Luxury Condo Escape, Sleeps 4

The Holiday Markets are here, escape to our spacious, furnished, 1 bedroom condo with a walkout balcony located in Friday Harbour All Seasons Resort community. Enjoy this season with access to walking trails, boardwalk festivities, live music, events and weekend markets on the boardwalk. Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, courtyard & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Lau

Waterfront home, city/sunset view & steps to beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minuts to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

Muskoka Cottage Getaway with Sauna

Welcome to your Lakefront Muskoka oasis, where epic sunrises greet you each morning and a private sauna awaits your return after a day on the lake. Surrounded by nature, this cozy retreat offers the perfect blend of relaxation and adventure, making it an ideal getaway for couples and families. Enjoy our fully updated outdoor space with a brand new deck, fire pit space and cedar barrel sauna that offers views of the lake. Located only a short 1.5 hour drive from Toronto.

Yurt in Mono

Sustainable Yurt Lodging close to the Bruce Trail. Glamping in style. There is plenty of privacy and nature to experience our 10-acre property. We harvest and sell teas from our herb gardens. Check online at Escarpment Gardens. Enjoy a soak in the hot tub, practice yoga, relax by the wood stove, or an outdoor campfire under the stars. Simple camp style cooking or eat at a great local restaurant within a 5 minute drive.

Boardwalk Bliss For Two *1 hr From TO!*

Waterfront Escape – 1 Hour from Toronto! Enjoy a private, street-level retreat steps from the marina boardwalk! Perfect for a relaxing getaway or remote work, with fast WiFi and in-room entertainment. 🌊 Activities Nearby: Waterside Dining & Boardwalk Music Nature Trails, Golf & Spa 🚤 Optional Add-Ons: ✔ Boating Excursions (Pre-Book) ✔ Dining & Activity Combos 📆 Book Now – Dates Fill Fast!

Sauna*King Bed*Fireplace*SmartTV

The perfect spa getaway an hour away from Toronto! Modern and bright fully stocked condo with a 2-3 person indoor sauna, fireplace, and an outdoor fire pit. Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen → Coffee & Espresso bar