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.

5 out of 5 average rating, 201 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!

4.99 out of 5 average rating, 156 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).

Home in Nestleton Station

4.99 out of 5 average rating, 166 reviews

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

4.94 out of 5 average rating, 168 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.

The living room features large windows offering views of the lake. Three comfortable couches are arranged around a wooden coffee table on a patterned rug. A floor lamp provides soft lighting, enhancing the cozy atmosphere of the space.

4.81 out of 5 average rating, 290 reviews

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

4.96 out of 5 average rating, 118 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

4.98 out of 5 average rating, 108 reviews

A circular cedar barrel sauna is nestled by the lake, surrounded by a circular seating area of black adirondack chairs. A fire pit with glowing embers sits at the center, while nearby torches provide soft lighting against a backdrop of autumn foliage.

Cottage in Gravenhurst

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.

Guest house in Victoria Harbour

Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.

4.96 out of 5 average rating, 283 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

4.84 out of 5 average rating, 129 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**

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.

4.99 out of 5 average rating, 103 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Welcome to a Bohemian Paradise in the Heart of Friday Harbour. Treat yourself to a relaxing experience only 1hr from Toronto. This beautifully designed condo was designed to make your experience at Friday Harbour the best it can be. **Convenience** One of the few condos with direct walkout to the courtyard’s Firepit and BBQs. Steps away from Restaurants, Nature Trails, Beach & Boardwalk, Golfing, Live Music Events every Weekend.

A modern living area features a dark sectional sofa and a round coffee table placed atop a patterned area rug. Large glass doors provide access to a balcony, while light pours in, illuminating the textured wall design. A beige accent chair adds to the inviting space.

4.85 out of 5 average rating, 127 reviews

*HotTub*Pool*FirePit*King Bed*

The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a year-round hot tub, outdoor pool, 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 → Year Round Hot Tub → Outdoor Swimming Pool

4.87 out of 5 average rating, 345 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

4.61 out of 5 average rating, 166 reviews

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

Lakeside Inn Cabin Apartment #2

A modern kitchen features sleek appliances, ample counter space, and cabinetry, creating an inviting cooking area. An expansive outdoor pool area is surrounded by lounge chairs, providing a relaxed atmosphere. The marina glows with lights, showcasing boats and waterfront amenities, encapsulating serene evenings by the water.

4.93 out of 5 average rating, 14 reviews

1BR Friday Harbour Retreat | Balcony + Pool Access

4.98 out of 5 average rating, 405 reviews

A hot tub is positioned on a wooden deck, surrounded by natural greenery. Nearby, a fire pit emits a warm glow, creating a cozy atmosphere. Soft outdoor lighting complements the setting, with views of the landscape visible in the background.

Flat in Bracebridge

The Muskoka River Chalet - The King's Den

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.

4.98 out of 5 average rating, 40 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.

4.93 out of 5 average rating, 55 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

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.

4.95 out of 5 average rating, 55 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

4.95 out of 5 average rating, 56 reviews

The outdoor area features a well-maintained lawn with green grass. A patio with colorful chairs is visibly arranged near a glass door, offering access to the unit. Striped awnings provide shade over the seating area, creating a relaxed space for outdoor enjoyment.

Flat in Orillia

RK's Bed & Breakfast

Waterfront house rentals

4.92 out of 5 average rating, 110 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

4.88 out of 5 average rating, 16 reviews

A private dock is shown extending into Sturgeon Lake, complemented by a spacious wooden deck. Four adirondack chairs are positioned along the edge, facing the water. Lush green grass surrounds the area, and a clear blue sky with fluffy clouds is visible above.

Home in Fenelon Falls

The Lake House in Fenelon Falls ~ Sturgeon Lake

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.

4.84 out of 5 average rating, 25 reviews

Couchiching Lake Retreat - Sauna! Near Downtown!

4.84 out of 5 average rating, 151 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

4.91 out of 5 average rating, 127 reviews

A spacious living room features large windows offering views of colorful foliage. A cozy fireplace is located on one side, with soft seating arranged comfortably around a central coffee table. Light wood flooring enhances the airy atmosphere.

Home in Bracebridge

River Luxe Muskoka 6BR 5BA w/ Hottub, Wifi 200mb+

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

A motorboat is docked alongside a wooden pier, which leads to a two-story home surrounded by greenery. The house features a deck with seating arrangements. The calm water reflects the exterior of the home and the surrounding trees.

4.9 out of 5 average rating, 72 reviews

The Big Yellow Waterfront House, on Lk Couchiching

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, 111 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

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, 242 reviews

2BR Getaway at Friday Harbour All Season Resort

The marina at twilight features calm waters reflecting the vibrant colors of the sunset. Multiple boats are docked along the well-lit marina, with modern buildings lining the shore, creating a serene and inviting atmosphere.

4.94 out of 5 average rating, 90 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

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 spacious patio area features comfortable grey woven furniture, including a seating set with cushions and a coffee table. A dining table with chairs is positioned nearby. The space is surrounded by glass panels, and a vibrant green plant adds a touch of color.

4.81 out of 5 average rating, 97 reviews

2 BR with a private terrace at Friday Harbour

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, 239 reviews

Designer Condo with beautiful harbour view.

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.

4.94 out of 5 average rating, 136 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.