
Waterfront vacation rentals in Simcoe County
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Simcoe County
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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!

Cozy Winter Escape - Ski, Hike & Chill by the fire
Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

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.

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.

Glass Dome - Sleep Under The Stars- Free Sundays
Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 $100/NIGHT ( 2 bunk beds)

Blue Dreams Of Lake Simcoe
Welcome to "Cabin Dreams Of Lake Simcoe" - your cozy blue cabin retreat in the heart of Hawkstone, Ontario, Canada. Immerse yourself in nature while enjoying modern comforts and nearby attractions. Our newly renovated 1 bedroom, 1 bathroom offers a unique getaway for couples, located just 1 1/2 hours outside of Toronto. **PLEASE NOTE** **Stairs leading up to the bed room loft are steep and may not be suitable for guests with mobility issues**

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

Boho by the Bay
BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." I encourage you to search eventsatfridayharbour to see what is seasonally available. if after searching, you still have questions or need clarification, please ask!
Popular amenities for Simcoe County waterfront rentals
Waterfront apartment rentals

Stunning 1 Bedroom unit

Beautiful Riverside Country Apartment

Lakeside Inn Cabin Apartment #2

Luxury Serene Escape @ Friday Harbour Resort

1BR Friday Harbour Retreat | Balcony + Pool Access

Modern Luxury Delight with a Pool and Hot Tub

Trendy 1 Bdrm w/Pool & Hot Tub View

Beautiful Modern 2 Bedroom Apt.
Waterfront house rentals

Underhill Riverside Retreat-Nature Preserve

2 Bd Boardwalk Condo Patio Oasis

Georgian Bay Paradise

Lakefront Retreat w/ Hot Tub, Game Room & Beach

Luxurious Lake House for Family Stays

Upper Shadow Creek Haven - Waterfront

Sunrise

Brewster's Lake Escape | Lakefront in Singhampton
Waterfront condo rentals

Cozy Stays – Your Fall Getaway at Friday Harbour

2BR Getaway at Friday Harbour All Season Resort

Luxury Getaway @ Friday Harbour Condo at Marina

Stylish getaway condo, resort living

Romantic Stay at Friday Harbour Resort Lake Simcoe

Designer Condo with beautiful harbour view.

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

Friday Harbour Luxury Condo Escape, Sleeps 4
Destinations to explore
- Cabin rentals Simcoe County
- Bed and breakfasts Simcoe County
- Rentals with breakfast Simcoe County
- Rentals with beach access Simcoe County
- Rentals with a washer and dryer Simcoe County
- Boutique hotels Simcoe County
- Luxury rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Apartment rentals Simcoe County
- Chalet rentals Simcoe County
- Vacation home rentals Simcoe County
- Rentals with a kayak Simcoe County
- Guesthouse rentals Simcoe County
- House rentals Simcoe County
- Dome rentals Simcoe County
- Pet-friendly rentals Simcoe County
- Villa rentals Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Tiny house rentals Simcoe County
- Family-friendly rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Rentals with a fire pit Simcoe County
- Cottage rentals Simcoe County
- Beachfront rentals Simcoe County
- Bungalow rentals Simcoe County
- Rentals with a patio Simcoe County
- Hotel rooms Simcoe County
- Rentals with pools Simcoe County
- Loft rentals Simcoe County
- RV rentals Simcoe County
- Rentals with a sauna Simcoe County
- Farmstay rentals Simcoe County
- Rentals with a home theater Simcoe County
- Rentals with an EV charger Simcoe County
- Private suite rentals Simcoe County
- Townhouse rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Waterfront rentals Ontario
- Waterfront rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Lakeridge Ski Resort
- Mount St. Louis Moonstone
- Craigleith Ski Club
- Angus Glen Golf Club
- Port Carling Golf & Country Club
- TPC Toronto at Osprey Valley
- Windermere Golf & Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Caledon Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- Wooden Sticks Golf Club
- The Georgian Bay Club
- Dagmar Ski Resort
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club




