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

Charming waterfront cottage on Lake Simcoe
Charming 4 bedroom cottage plus Boat house conveniently located 1 hour from GTA on a private waterfront lot surrounded by mature trees sandy bottom clear water. Proximity of the cottage to the water is sure to please either the sun or shade lovers with multiple large decks dock for sitting dining and lounging. We offer hot tub Sauna basketball net paddle boat floating mat kayaks canoe paddle board pool table, foosball. fishing gear, life jackets. Summertime is by the week, Saturday to Saturday.

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!

Cozy Lakeside Cottage on Lake Scugog
WELCOME TO OUR COZY COTTAGE! This rustic, private, lakefront cottage (north shore of Lake Scugog) 2 bedrooms (1 queen, 1 full/double sized bed), large bright sunroom with sleeper sectional. Large newly renovated deck. You are sure to enjoy the lake view, large private dock, water facing deck with bbq, huge yard for games, bon fires and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for couples or friends to escape the hustle and bustle, relax and unwind.

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).

Lake Simcoe Retreat
Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

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.

Granny's Cottage
Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

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.

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.

Cottage on Lake Simcoe Amazing lake Views
Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

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

Lakeside Guest Suite, on Lake Scugog, Port Perry
WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.
Popular amenities for Lake Simcoe kayak rentals
Holiday House Rentals with a Kayak

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Cottages with a kayak

D O C K | NEW Modern Muskoka Waterfront 2+1 bed

CozyPeaceful LakeCottage HotTub Canada

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Riverfront Cottage with HotTub

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Spacious Cottage Escape with Lakeside Hot Tub

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Haven at Georgian Bay
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake

Waterfront A-frame Retreat with Sauna & Hot tub

LakeKabin: Lakefront, HotTub, Arcade, Kayaks&SUP

18 Acres of Summer Fun: Dock, Games Room, River

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Retreat style cottage + wood fired sauna

The Beautiful Sandy Lake Cabin (as seen on HGTV)

Scandi Wellness Getaway for 2 w/ Hot Tub | Sauna
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Niagara Falls Holiday rentals
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- Rentals with pools Lake Simcoe
- Rentals with a hot tub Lake Simcoe
- Beachfront rentals Lake Simcoe
- Guesthouse rentals Lake Simcoe
- Family-friendly rentals Lake Simcoe
- Luxury rentals Lake Simcoe
- Rentals with a sauna Lake Simcoe
- Rentals with a fireplace Lake Simcoe
- Smoking-friendly rentals Lake Simcoe
- Apartment rentals Lake Simcoe
- Cabin rentals Lake Simcoe
- Cottage rentals Lake Simcoe
- Rentals with a patio Lake Simcoe
- Rentals with lake access Lake Simcoe
- Townhouse rentals Lake Simcoe
- Rentals with breakfast Lake Simcoe
- Bungalow rentals Lake Simcoe
- Fitness-friendly rentals Lake Simcoe
- Rentals with beach access Lake Simcoe
- Condo rentals Lake Simcoe
- Rentals with an EV charger Lake Simcoe
- Lakehouse rentals Lake Simcoe
- Rentals with a fire pit Lake Simcoe
- Ski-in/ski-out rentals Lake Simcoe
- Rentals with outdoor seating Lake Simcoe
- Pet-friendly rentals Lake Simcoe
- Waterfront rentals Lake Simcoe
- House rentals Lake Simcoe
- Private suite rentals Lake Simcoe
- Rentals with a washing machine and dryer Lake Simcoe
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Toronto Zoo
- Rouge National Urban Park
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Cedar Park Resort
- Craigleith Ski Club
- Gull Lake
- Port Carling Golf & Country Club
- Angus Glen Golf Club
- Lakeridge Ski Resort
- Mount St. Louis Moonstone
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- The Club At Bond Head
- Windermere Golf & Country Club
- Wooden Sticks Golf Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Dagmar Ski Resort
- Toronto Ski Club
- Granite Golf Club