Waterfront holiday rentals in Penetanguishene

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, 213 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!

4.97 out of 5 average rating, 125 reviews

A spacious living area is highlighted by a large white stone fireplace, surrounded by comfortable seating. Natural light filters through sheer curtains, enhancing the warm atmosphere. A flat-screen television is mounted above the fireplace, and a wooden dining table sits elegantly in the foreground.

Cottage in Tiny

Summer Getaway - 3 min walk to Beach, Clean & Cozy

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

4.99 out of 5 average rating, 214 reviews

Townhouse in Port Severn

Pool, Wifi, Free parking, Golf, Laundry, BBQ

Welcome We share with you our ⭐️⭐️⭐️⭐️⭐️ ‘super clean’ and pet friendly home -Free parking, -EV Charger, -Fast Wifi, -Indoor Fireplace (downstairs in the winter months only) -two outdoor fire pits (Solo Stove) -Full Kitchen, -Air Conditioning, -Peloton, -Hot Tub -Loft -Smart TV, -Washer and Dryer Oak Bay Golf Course, large yard, seasonal shared pool. Children's supplies -Crib, -toys, -playmat and custom dog 🐾house Minutes from Georgian Bay Island National Park in Muskoka.

4.94 out of 5 average rating, 143 reviews

A view of the cottage from a rocky outcrop showcases its modern design. The structure features large windows and a deck, surrounded by lush greenery. Trees with autumn foliage frame the scene, while a fenced yard provides privacy.

Cottage in Waubaushene

Forest Harbour Hideaway

Situated on beautiful Georgian Bay, this cozy waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock and our brand new custom sauna, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Find a variety of shops, restaurants and local attractions in Midland and Orillia (both a 20 minute drive) like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre!

4.94 out of 5 average rating, 270 reviews

The exterior of a custom-built log cabin is framed by trees under a clear blue sky. A spacious porch features two Adirondack chairs and a fire pit, providing a welcoming outdoor space. Natural stone accents enhance the cabin's rustic charm.

Chalet in Gravenhurst

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

5 out of 5 average rating, 267 reviews

A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.

Cabin in Bracebridge

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

4.81 out of 5 average rating, 108 reviews

The charming exterior of the bunkie features rustic wooden siding and three large windows. A welcoming front porch is furnished with two chairs and a small table, surrounded by a natural landscape of trees and open space, showcasing the tranquility of the setting.

Tiny home in Coldwater

Bunkie On The River

Welcome to our four season bunkie retreat on the river. Leave the world behind and seek comfort and peace at Riverside Ranch. Imagine starting your day reconnecting with nature amidst wooded walking trails. Along your walk you see geese swimming in the river, goats exploring the woods, and Highland cattle grazing in the pasture. Upon return, you open the door to the crackle & pop of a toasty wood burning sauna, followed by an icy cold plunge in the river. *No air-conditioning*

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, 291 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

4.96 out of 5 average rating, 108 reviews

A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.

Cottage in Tiny

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

4.98 out of 5 average rating, 418 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

Welcome to Muskoka River Chalet! **Please read full listing description before booking.** Relax in your fully private one-bedroom walkout apartment with private kitchen, cozy living room, featuring smart TVs and toasty fireplaces. Explore our shared outdoor spaces along 60' of waterfront. Indulge in the hot tub for relaxation. Just minutes walking to town for shopping, dining, and nightlife. Book now for a perfect blend of comfort and convenience!

4.97 out of 5 average rating, 250 reviews

A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.

Cottage in Torrance

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

4.92 out of 5 average rating, 111 reviews

A hot tub is positioned beneath a covered patio, offering views of the waterfront. The clear water of the hot tub contrasts with the lush green surroundings and the calm blue of the lake in the distance. Sunlight filters through the patio overhead.

Home in Port McNicoll

Breathtaking 5 bedroom Waterfront Home W/ Hot Tub!

Stunning five-bedroom waterfront home on Georgian Bay! Located in a quiet area with stunning views and amazing sunsets! In the summer, the lake is perfect for swimming, kayaking, paddle boarding or fishing! Just bring water shoes as there are some rocks and zebra muscles. Equipped with a hot tub overlooking the lake, this five-bedroom waterfront home is perfect for a summer or winter getaway! *Please note this cottage is Pet Free.

Popular amenities for waterfront rentals in Penetanguishene

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 329 reviews

A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.

Flat in Horning's Mills

Beautiful Riverside Country Apartment

4.86 out of 5 average rating, 21 reviews

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.

Flat in Innisfil

1BR Friday Harbour Retreat | Balcony + Pool Access

4.93 out of 5 average rating, 27 reviews

Flat in Innisfil

2 Bedroom Luxury Suite @ Friday Harbour Resort

4.95 out of 5 average rating, 57 reviews

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.

Flat in Innisfil

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

4.94 out of 5 average rating, 50 reviews

A deck area is furnished with several red Adirondack chairs and a fire pit, inviting relaxation by the waterfront. Lush greenery borders the space, while a wooden dock extends into the calm bay, offering scenic water vistas and a tranquil ambiance.

Flat in Port Mcnicoll

Welcome to waterfront paradise on Georgian Bay

4.95 out of 5 average rating, 61 reviews

A light-filled studio apartment features a modern kitchen with stainless steel appliances and white cabinetry. A spacious grey sofa is positioned near a wooden dining table with stools. Large windows allow natural light to illuminate the open living area, enhancing its fresh appearance.

Flat in Midland

MegaMindful Living Air BnB Two

4.95 out of 5 average rating, 58 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

4.96 out of 5 average rating, 27 reviews

A sandy beach stretches out towards calm waters, complemented by a small dock and an island visible in the distance. Red and gray Adirondack chairs are setup in a semicircle on the beach, inviting relaxation under a clear blue sky dotted with clouds.

Home in Victoria Harbour

Welcoming Waterfront Cottage

4.72 out of 5 average rating, 29 reviews

Home in Bracebridge

Muskoka Private Waterfront Cottage | Sauna | Kayak

4.88 out of 5 average rating, 33 reviews

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.

Home in Orillia

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

4.95 out of 5 average rating, 19 reviews

A serene waterfront scene captures calm water reflecting vibrant autumn foliage. Mist gently rises from the lake's surface, while a clear blue sky is partially adorned with a soft white moon. The landscape includes various trees, creating a peaceful natural environment.

Home in Kirkfield

Life is Better at the Cottage

4.91 out of 5 average rating, 139 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 Luxury Muskoka 6BR 5BA w/ Hottub, Wifi 200mb+

4.87 out of 5 average rating, 101 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

4.93 out of 5 average rating, 15 reviews

A charming red A-frame cottage is displayed, featuring large front windows and a white balcony. Two classic Adirondack chairs sit invitingly on the wooden deck. Surrounding greenery and a gravel pathway enhance the natural setting.

Home in Elmvale

The Red A-frame Cottage

5 out of 5 average rating, 17 reviews

A hot tub is positioned in the foreground, bubbling gently under a twilight sky. In the background, a modern lakefront cottage with extensive glass windows offers views of the surrounding nature. A well-maintained yard features a pathway leading to the cottage and additional outdoor seating.

Home in Victoria Harbour

Sunrise

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, 117 reviews

Golf, Spa & Spring Vibes 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, 246 reviews

2BR Getaway at Friday Harbour All Season Resort

An aerial view captures the expansive layout of Friday Harbour, showcasing various buildings along the marina and natural surroundings. A peaceful golf course is visible with a distinctive lighthouse, all framed by serene water reflections under a twilight sky.

4.91 out of 5 average rating, 100 reviews

Family-friendly luxury getaway at Friday Harbour

4.98 out of 5 average rating, 103 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, 187 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.

4.82 out of 5 average rating, 103 reviews

Pet friendly 2 BR with a private terrace at FH

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.

4.93 out of 5 average rating, 246 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.