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

Cozy Lakeside Cottage on Lake Scugog
WELCOME TO OUR COZY ALL SEASONS COTTAGE! This rustic private lakefront cottage (north shore of Lake Scugog) 2 bedrooms (1 queen, 1 full/double), 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.

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.

Cozy, Quirky and Modern Lakefront Cottage
Welcome to the Scugog Sugar Shack! Just 70 mins away from Toronto, escape to enjoy picturesque sunsets at this cozy lakefront cottage nestled under the largest collection of mature sugar maples on Scugog Point. This 2 bedroom open concept 1940s cottage has been updated with all the creature comforts while staying true to its quirky roots. With private access to Lake Scugog, known for fishing, kayaking, paddle boarding and swimming, bask in the sun all day & sit by a fire under the stars.

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.

The Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Muskoka Hideaway-hot tub/private trails/wood stove
Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

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.

Upscale Spa Getaway w/ Private Sauna
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Luxurious - Waterfront Cottage
This beautiful luxury cottage will just wow you from the moment you enter. Clean shallow shoreline great for swimming. Has all amenities you will need and is about 10 minutes south of Haliburton. Cottage has Washer/Dryer, Wi-Fi, Lots of Parking, Large Fire Pit, Kayaks, Canoes, Sleds (winter),Pedal Boat, Life Jackets, Coffee Machine (with coffee), Tea Kettle, Hot Tub, Sauna, BBQ and TV. Lake is great for fishing, beautiful trails for trekking. Full linens and towels included.
Popular amenities for kayak rentals in Lake Simcoe
House rentals with a kayak

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

HyggeHaus—sleek snuggly secluded ski-in/out cabin

Couchiching Lake Retreat - Sauna! Near Downtown!

Year-Round Heated Pool & Hot Tub Family Oasis

Beautiful Quiet Escape to Bobcaygeon, Kawarthas

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

Modern Riverfront Escape w/Sauna, Gym, Dock

Lively Lakehouse with hot tub
Cottage rentals with a kayak

“Lakeside Dreams”: All season HotTub w/lake views

Riverfront Cottage with HotTub

White Oak on Cardinal - Cozy Cottage in Kawarthas

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Spacious Cottage Escape with Lakeside Hot Tub

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

Charming waterfront cottage on Lake Simcoe

Resort-Style Luxury Waterfront Cottage
Cabin rentals with a kayak

Waterfront A-frame Retreat with Sauna & Hot tub

LakeKabin: Lakefront, HotTub, Arcade, Kayaks&SUP

Newly Renovated boathouse on Balsalm Lake

Vintage Hollywood Cabin: Hot Tub/ BBQ/Sauna/ Beach

The Beach Deck Retreat

Lux Cabin | Hot Tub | Sauna | Lake | Pet Friendly

Retreat style cottage + wood fired sauna

The Beautiful Sandy Lake Cabin (as seen on HGTV)
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Niagara Falls Holiday rentals
- Island of Montreal Holiday rentals
- St. Catharines Holiday rentals
- Northeast Ohio Holiday rentals
- Pittsburgh Holiday rentals
- Montreal Holiday rentals
- Laurentides Holiday rentals
- Erie Canal Holiday rentals
- Rentals with a firepit Lake Simcoe
- Beachfront rentals Lake Simcoe
- Smoking-friendly rentals Lake Simcoe
- Rentals with pools Lake Simcoe
- Townhouse rentals Lake Simcoe
- Rentals with outdoor seating Lake Simcoe
- Pet-friendly rentals Lake Simcoe
- Lakehouse rentals Lake Simcoe
- Cottage rentals Lake Simcoe
- Rentals with a patio Lake Simcoe
- Rentals with an EV charger Lake Simcoe
- Rentals with lake access Lake Simcoe
- Rentals with breakfast Lake Simcoe
- Luxury rentals Lake Simcoe
- Family-friendly rentals Lake Simcoe
- Guest house rentals Lake Simcoe
- Ski-in/ski-out rentals Lake Simcoe
- Rentals with a washing machine and dryer Lake Simcoe
- Rentals with a sauna Lake Simcoe
- Cabin rentals Lake Simcoe
- Private suite rentals Lake Simcoe
- Rentals with a hot tub Lake Simcoe
- Waterfront rentals Lake Simcoe
- Rentals with beach access Lake Simcoe
- Apartment rentals Lake Simcoe
- Bungalow rentals Lake Simcoe
- House rentals Lake Simcoe
- Rentals with a fireplace Lake Simcoe
- Flat rentals Lake Simcoe
- Fitness-friendly rentals Lake Simcoe
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Blue Mountain Village
- Toronto Zoo
- Snow Valley Ski Resort
- Rouge National Urban Park
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Cedar Park Resort
- Gull Lake
- Lakeridge Ski Resort
- Angus Glen Golf Club
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Windermere Golf & Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- Wooden Sticks Golf Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Dagmar Ski Resort
- Toronto Ski Club
- Black Diamond Golf Club




