Waterfront holiday rentals in Orillia

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

4.99 out of 5 average rating, 190 reviews

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!

4.96 out of 5 average rating, 145 reviews

A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.

Cottage in Severn Bridge

CARL in Muskoka: Waterfront Cottage with Hot Tub

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

4.99 out of 5 average rating, 151 reviews

A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.

Cottage in Washago

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

4.94 out of 5 average rating, 159 reviews

The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.

Cabin in Innisfil

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.

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

4.93 out of 5 average rating, 200 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

4.92 out of 5 average rating, 108 reviews

Cottage in Orillia

Couples retreat w/hot tub: Romantic Getaway

Escape to tranquility in this spacious, serene home, now offered at an affordable rate for couples seeking a private retreat. Enjoy exclusive access to the entire property. Nestled along a canal leading to Lake Simcoe, this stunning home features a fully-equipped kitchen, outdoor BBQ, and a cozy firepit. Unwind in your private hot tub overlooking the water, or relax in the comfortable living and dining area. With fast Wi-Fi and beautiful surroundings, it's the perfect romantic getaway.

4.96 out of 5 average rating, 117 reviews

A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.

Cottage in Washago

Waterfront Cottage sauna/golf/kayaks/beach/games

Welcome to Hally’s Cove Riverside Retreat! A fully loaded 4-season escape on the Trent Severn River! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖‍♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Summer Bonus - Mosquito-sprayed for extra comfort! IG to see more photos: @hallys_cove

4.92 out of 5 average rating, 272 reviews

The cozy living room features wooden walls and a gas stove. Natural light streams through large windows, illuminating a comfortable white sofa and a wooden coffee table. A textured rug lies beneath, complementing a minimalist aesthetic with a few decorative elements.

Cabin in Washago

Black River Haus - Scandi Riverfront Cabin Muskoka

Follow us on IG: @visitblackriverhaus The Black River Haus is a Scandi-inspired renovated 1970s cabin offering 3 beds + 1 bath and 140 ft riverfront near Muskoka, Ontario (20 min to Gravenhurst & Orillia). The cabin has been renovated and designed with the surrounding nature in mind, featuring a rustic living room & fireplace, fully-equipped kitchen and an outdoor patio & firepit. The Black River is 30 km long and is perfect for kayaking, canoeing and exploring.

4.83 out of 5 average rating, 119 reviews

The cozy blue cabin is nestled among trees, showcasing a sloped roof and a vibrant yellow front door. Natural surroundings provide a serene backdrop, while a gravel path leads to the entrance, hinting at a peaceful retreat in the heart of nature.

Cabin in Hawkestone

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**

4.87 out of 5 average rating, 219 reviews

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. A living area boasts modern furniture, including a sofa and seating around a fire pit. The outdoor pool area is highlighted, alongside the exterior view of the building, showcasing multiple levels.

Home in Innisfil

King Bed*Pool*Fireplace*BBQ*Smart TV

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a king bed and queen pull out loaded with entertainment from TVs (Netflix, Amazon Prime, Disney+) to the best board games! 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

4.94 out of 5 average rating, 123 reviews

The exterior of a cottage is shown, surrounded by lush greenery and blooming flowers. A stone pathway leads to the entrance, with a wooden deck overlooking the lake. The tranquil water and open sky are visible in the background, accented by a large tree providing shade.

Cottage in Orillia

Spacious Cottage Escape with Lakeside Hot Tub

Escape from the usual! Bring your crew to our spacious 5 bdrm, 2 washroom, Lake Front cottage and RELAX. Enjoy the warmth of the fireplace and the beautiful view from the sunroom. Soak in the hot tub and watch the sunset. Proximity to Orillia's shops and restaurants. Casino Rama is 2km away for a completely different kind of fun. Two adult Kayaks available in spring and fall. Hot tub and bbq year round.

4.87 out of 5 average rating, 340 reviews

An aerial view captures a waterfront community at sunset, featuring modern buildings along the marina. Boats are docked at the waterfront, and a serene lake reflects the warm colors of the sky. Lush greenery lines the horizon, adding a sense of tranquility.

Cottage in Innisfil

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!

Popular amenities for waterfront rentals in Orillia

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.83 out of 5 average rating, 65 reviews

The living room features a comfortable leather reclining sofa and a simple grey couch, complemented by a coffee table and a media stand with a television. Natural light filters through the large windows adorned with light curtains, creating a bright and welcoming atmosphere.

Flat in Alliston

Stunning 1 Bedroom unit

The cabin's exterior displays a simple design with a light-colored facade, complemented by green grass and a gravel pathway. Two red chairs are positioned in front, inviting relaxation. Nearby, a large tree provides shade, while other cabins are visible in the background.

Flat in Orillia

4.61 out of 5 average rating, 163 reviews

Lakeside Inn Cabin Apartment #2

A wooden ladder-style shelf displays decorative items against a soft gray wall. A bright yellow 'Smile' sign sits above a framed print titled 'DREAM' on a small easel. A lantern and a decorative floral arrangement complete the scene.

4.89 out of 5 average rating, 35 reviews

Luxury Serene Escape @ Friday Harbour Resort

An outdoor seating area is furnished with a large sectional sofa and a table, providing a comfortable space for relaxation. The balcony overlooks a pool surrounded by greenery and modern buildings, offering a serene view of the outdoor amenities.

4.97 out of 5 average rating, 38 reviews

Modern Luxury Delight with a Pool and Hot Tub

A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.

4.98 out of 5 average rating, 51 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

4.67 out of 5 average rating, 3 reviews

A cozy bedroom features a double bed adorned with several soft pillows against a calming gray wall. Light filters through sheer curtains, illuminating the space, complemented by a modern bedside lamp. An art piece sits above a small table, adding a personal touch.

Flat in Barrie

Beautiful Modern 2 Bedroom Apt.

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

4.94 out of 5 average rating, 53 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

4.96 out of 5 average rating, 24 reviews

A cozy bedroom features a spacious bed adorned with patterned bedding. A wooden dresser is positioned nearby, and a lamp provides soft lighting. Natural light filters through the window, which is dressed with dark curtains, and rustic wooden walls contribute to the cabin's charm.

Flat in Tiny

Cabin A in Wymbolwood Lodge

Waterfront house rentals

4.95 out of 5 average rating, 108 reviews

A spacious backyard features a fire pit surrounded by four adirondack chairs. The cottage showcases large windows and a deck with outdoor dining furniture and an umbrella. Two kayaks are stored nearby, adding to the lakefront atmosphere.

Home in Little Britain

Cozy Lakeside Cottage on Lake Scugog

An outdoor firepit is surrounded by stone, with flames flickering invitingly. Adjacent, a wooden Adirondack chair faces a serene lake, reflecting warm sunset hues. A charming playhouse stands nearby, nestled among mature trees, creating a peaceful lakeside setting.

4.83 out of 5 average rating, 24 reviews

Couchiching Lake Retreat - Sauna! Near Downtown!

4.84 out of 5 average rating, 149 reviews

A serene sunset is captured over Georgian Bay, with warm orange and gold hues reflecting on the water. Silhouetted figures are seated on a dock, gazing out towards the horizon, creating a sense of tranquil evening ambiance.

Home in Victoria Harbour

Georgian Bay Paradise

A living room is framed by an open doorway, showcasing two comfortable seating areas. A round coffee table is positioned in the center of the room, surrounded by plush sofas. Natural light filters through a window, with sheer curtains enhancing the brightness.

4.92 out of 5 average rating, 12 reviews

Mariposa Century Home - Heritage Pocket Orillia

The cottage exterior is illuminated at dusk, showcasing its modern design. Large windows reveal the open-concept interior, while a spacious deck offers seating options. The surrounding landscape features a manicured lawn and trees in the background, enhancing the serene lakeside setting.

4.84 out of 5 average rating, 19 reviews

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

A modern condominium building is displayed, featuring a mix of white and dark gray exterior walls. Windows are arranged symmetrically, and small trees are placed along the walkway. A pathway leading to the entrance is visible, enhancing the building's contemporary design.

5 out of 5 average rating, 13 reviews

Orilluxstay

A spacious living room features a comfortable sectional sofa arranged around a wooden coffee table. A large flat-screen television is mounted on the wall. Decorative plants and framed artwork enhance the cozy atmosphere, while ample natural light illuminates the space.

4.9 out of 5 average rating, 21 reviews

Upper Shadow Creek Haven - Waterfront

4.92 out of 5 average rating, 232 reviews

Home in Bracebridge

The Muskoka River Homestead

Waterfront apartment rentals

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 110 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

A spacious living area features a comfortable couch and coffee table surrounded by decorative plants. Large windows provide ample natural light, framed by light-colored curtains. A stylish chandelier hangs overhead, and a wall-mounted TV offers entertainment options, creating a relaxing and inviting environment.

5 out of 5 average rating, 77 reviews

Luxury Stay at Friday Harbour Resort Lake Simcoe

An aerial view captures Friday Harbour Resort, highlighting its serene waterways and lush green landscapes. The sprawling development showcases a variety of buildings alongside the water, with a beach club pool visible in the foreground. The scene is framed by trees and the horizon over Lake Simcoe.

4.86 out of 5 average rating, 240 reviews

2BR Getaway at Friday Harbour All Season Resort

4.98 out of 5 average rating, 93 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

A comfortable outdoor balcony area features two lounge chairs and a glass-top table. Planters with various plants are positioned around the space, enhancing the natural ambiance. A textured rug adds warmth, completing the inviting outdoor setting.

4.94 out of 5 average rating, 178 reviews

Stylish getaway condo, resort living

A wide wooden boardwalk is shown alongside a marina, with modern buildings lining the waterfront. Soft sunlight reflects off the water and the boats docked. Comfortable blue chairs are placed on the green lawn, inviting relaxation while enjoying the serene harbor view.

4.94 out of 5 average rating, 237 reviews

Designer Condo with beautiful harbour view.

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.

4.88 out of 5 average rating, 154 reviews

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

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.