Waterfront holiday rentals in Penetanguishene

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Penetanguishene

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
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.
Apartment in Innisfil
4.99 out of 5 average rating, 188 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!

Top guest favourite
A winterized cottage is surrounded by snow-covered terrain and tall trees. The exterior features large windows and a wraparound deck, offering views of the natural landscape. A black railing lines the deck, and a snow-dusted pathway leads to the entrance.
Cottage in Tiny
4.97 out of 5 average rating, 127 reviews

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

Guest favourite
Cottage in Bracebridge
4.89 out of 5 average rating, 118 reviews

Cozy Muskoka River Cottage - Canoe, BBQ, Fire Pit

Retreat in the heart of Muskoka, come enjoy the sparkling calm of Muskoka River. Inside offers an open concept kitchen, living and dining area and two bedrooms facing a forested backyard with a walk-out deck. Fire up the BBQ on the front patio or toast marshmallows by the river at your new waterside oasis. ☃️❄️ From ice skating trails, winter fests and tubing to dog sledding, snowshoeing and sleigh rides — winter at the cottage is exciting, tranquil and beautiful. Ask us for recommendations!

Guest favourite
Cottage in Tiny
4.97 out of 5 average rating, 145 reviews

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.

Top guest favourite
A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.
Cottage in Georgian Bay
4.98 out of 5 average rating, 129 reviews

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Top guest favourite
A modern cottage is set against a backdrop of tall trees, featuring a large wraparound deck illuminated by warm lights. A fire pit sits on a granite outcrop, surrounded by outdoor chairs. The peaceful evening sky casts a calm ambiance over the scene.
Cottage in Bracebridge
4.99 out of 5 average rating, 146 reviews

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage with loft is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

Top guest favourite
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
5 out of 5 average rating, 240 reviews

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.

Top guest favourite
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
4.84 out of 5 average rating, 149 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Top guest favourite
The cottage features a contemporary design with large glass windows, reflecting autumn foliage and the serene lake surrounding it. A deck offers outdoor seating with steps leading down to a small dock where canoes are moored, nestled among lush trees.
Treehouse in Utterson
4.96 out of 5 average rating, 233 reviews

The Water’s Edge * * Unique Muskoka Treehouse * *

CottageCreators presents a once-in-a-lifetime (or as often as you’d like!) Muskoka escape. Perched among the treetops on one of the region’s most stunning lakes, this rustic-luxury retreat offers a floating hammock net, two-sided indoor/outdoor fireplace, and private dock for swimming, canoeing, kayaking and SUP. Fall asleep to the gentle sounds of the lake, wake up to sunrise through the trees, and unwind in total seclusion—just you, the forest, and the water.

Top guest favourite
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.
Guest house in Victoria Harbour
4.96 out of 5 average rating, 280 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

Top guest favourite
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
4.96 out of 5 average rating, 100 reviews

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2024-231 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.

Top guest favourite
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
4.97 out of 5 average rating, 240 reviews

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.

Popular amenities for waterfront rentals in Penetanguishene

Quick stats about waterfront rentals in Penetanguishene

  • Total holiday rentals

    Explore 30 holiday rentals in Penetanguishene

  • Nightly prices starting at

    Penetanguishene holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 of Penetanguishene holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penetanguishene rentals

  • 4.8 Average rating

    Penetanguishene stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Penetanguishene
  6. Waterfront rentals