
Holiday rentals with a kayak in Penetanguishene
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Top-rated Accommodation with a Kayak in Penetanguishene
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat
4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

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.

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.

Forest Harbour Hideaway
Situated on beautiful Georgian Bay, this cozy and quaint waterfront cottage delivers an escape from reality with all the comforts of home! With private access to the water and dock, and two public beaches within a 5 minute walk, unwind, relax and reset in the heart of our quiet cottage neighbourhood. Both Midland and Orillia are 20 minutes away by car, where you can find a variety of shops, restaurants and local attractions, like Sainte-Marie Among the Hurons and Wye Marsh Wildlife Centre.

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.

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.

The Bay View Cottage w/hot tub
Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Stix N Stones (Includes Light Breakfast & Kayaks)
Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

The Hudson - Riverside Cabin, Bracebridge
Nestled in the pines on the Muskoka River is this cozy one-bedroom cottage, ideal for a couple’s retreat. The Hudson offers the best of all worlds: it is relaxing, tranquil, and private, but you’re only a 10-minute drive from the Town of Bracebridge with unique shops, restaurants, groceries, and breweries, not to mention numerous tourist attractions. Marked trails are direct across the river. For more photos and information visit us on IG (at) thehudson.riversidecabin

Gorgeous Muskoka Getaway on stunning private lake
Enjoy the perfect cozy Muskoka cottage "The Perch" on a beautiful private lake. This family and pet-friendly home is your year-round retreat. Your family will be close to everything when you stay at this centrally located place but you will feel like you are at a peaceful cottage surrounded by nature. With all of the amenities that you would need, you will find that The Perch is everything you are looking for to create memories with friends, families or a loved ones.

Teremok Cabin at Zukaland | Cedar Hot Tub & Sauna
Welcome to Teremok Log Cabin at Zukaland, a unique Slavic-style tiny cabin nestled among mature pines on a scenic forested cliff in Muskoka. Enjoy peaceful woodland surroundings with easy access to a sandy beach by the Muskoka River. Guests may enhance their stay with optional add-on experiences, including breakfast in bed or our Cedar Outdoor Spa with wood-fired hot tub and sauna. As evening falls, cozy up by the warmth of a real wood stove and unwind in nature.

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.
Popular amenities for Penetanguishene kayak rentals
Holiday House Rentals with a Kayak

Welcoming Waterfront Cottage

River's End: Explore the river by kayak or canoe!

Couchiching Lake Retreat - Sauna! Near Downtown!

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

168 Fairway to Ski View Retreat

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The Muskoka River Homestead

Waterfront Cottage in Gravenhurst, Muskoka
Cottages with a kayak

Waterfront cottage on quiet Spence lake

Waterfront Cottage in Muskoka | SAUNA | Beach

Riverfront Cottage with HotTub

Waterfront @Muskoka Pines /kayaks/bbq/firepit

Vintage Lakeview Cottage w/ Fireplace -Four-Season

Muskoka Cottage Getaway with Sauna

Luxury Lakehouse Hot Tub Private Beach Lake Simcoe

CARL in Muskoka: Waterfront Cottage with Hot Tub
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

Gorgeous Cottage @ Go Home Lake

The Blue Cottage

The Nest Lakehouse - Hot Tub, Innisfil Beach Park

Gorgeous Muskokan Cottage on Six Mile Lake

Beautiful Six Mile Lake Muskoka

Sparrow Lake Lakeside Cottage

Misty River Cabin Private Waterfront Pet-Friendly!
Quick stats about holiday rentals with a kayak in Penetanguishene

Total holiday rentals
Explore 20 holiday rentals in Penetanguishene

Nightly prices starting at
Penetanguishene holiday rentals start at $113 AUD per night before taxes and fees

Verified guest reviews
Over 740 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Penetanguishene holiday rentals include Wi-Fi 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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- The Ridge at Manitou Golf Club
- Three Mile Lake
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Kee To Bala
- Torrance Barrens Dark Sky Conservation Area
- Taboo Muskoka Resort & Golf
- Burl's Creek Event Grounds
- Innisfil Beach Park
- Bass Lake Provincial Park
- Awenda Provincial Park
- Casino Rama Resort
- Wye Marsh Wildlife Centre
- Menominee Lake
- Orillia Opera House
- Centennial Beach
- Couchiching Beach Park




