Vacation rentals with a kayak in Georgina

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Top-rated kayak rentals in Georgina

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Guest favorite

A wooden deck overlooks tranquil waters, featuring two red Adirondack chairs facing the lake. The beautifully colored sky at sunset casts a serene ambiance, surrounded by lush greenery and trees providing a natural frame.

Cottage in Brechin

4.92 out of 5 average rating, 172 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect spot for bringing together family and friends. Here, laughter fills the home, and nature's beauty is right outside your door. Dive into clear waters for some fun kayaking and boating, and wake up to beautiful sunrises from our private dock. Take a walk on scenic paths, enjoy outdoor BBQs, and paddle around in our kayaks. Book your special getaway today and start making heartwarming memories that last.

Superhost

A wooden dock extends towards the lake, framed by lush trees on either side. The cottage is visible in the background, surrounded by greenery, with calm waters lapping at the shores. The sky is partly cloudy, adding to the serene lakeside atmosphere.

Cottage in Keswick

4.87 out of 5 average rating, 160 reviews

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

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Guest favorite

A spacious deck features a large table surrounded by chairs and an orange umbrella providing shade. The deck overlooks the lake, with green grass and trees in the background. Lounge chairs are positioned along the shoreline, inviting relaxation by the water.

Home in Little Britain

4.96 out of 5 average rating, 99 reviews

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.

Guest favorite

The image showcases a scenic waterfront view featuring a private dock extending toward a charming cottage. Vibrant red chairs are positioned on the lawn, surrounded by lush greenery. The calm water reflects the blue sky, creating a serene atmosphere for relaxation.

Cottage in Georgina

4.96 out of 5 average rating, 117 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Guest favorite

A covered deck is equipped with a round dining table surrounded by white chairs, overlooking a sandy beach and the water. Soft string lights create a gentle ambiance, while chairs invite relaxation. The view extends over Georgian Bay, highlighting the tranquil shoreline.

Cottage in Tiny

4.97 out of 5 average rating, 129 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 favorite

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.

Condo in Innisfil

5 out of 5 average rating, 166 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own 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! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Top guest favorite

Home in Nestleton Station

4.99 out of 5 average rating, 139 reviews

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.

Top guest favorite

The living area features large windows that offer views of the expansive lawn. A wooden coffee table is centered between a floral-patterned couch and a comfortable armchair. Light wood flooring complements the cozy atmosphere of the room.

Cottage in Keswick

4.99 out of 5 average rating, 165 reviews

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.

Guest favorite

A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.

Condo in Innisfil

4.93 out of 5 average rating, 185 reviews

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

Top guest favorite

A serene view is presented through large glass windows, showcasing a snowy landscape at dusk. The soft colors of the sunset reflect over the lake, with trees lining the horizon. A cozy chair is positioned on the porch, inviting relaxation amidst the tranquil setting.

Cottage in Brechin

4.92 out of 5 average rating, 109 reviews

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.

Top guest favorite

Guesthouse in Port Perry

5 out of 5 average rating, 119 reviews

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.

Top guest favorite

A circular patio area features a fire pit at the center, surrounded by eight colorful Muskoka chairs in red and blue. The setting overlooks a serene lake and wooden dock, with a guitar resting nearby on the lawn, framed by a clear blue sky and scattered clouds.

Home in Keswick

4.91 out of 5 average rating, 281 reviews

Luxury Lakefront Hot Tub Private Beach Lake Simcoe

✨Perfect Family & Friends Getaway on Lake Simcoe Escape to a luxury Lake Simcoe waterfront retreat with private sandy beach, hot tub under the stars, kayaks, SUP, lily pad, and kids’ sand play area. Enjoy a lakeview open kitchen, 14-seat dining table, 3 family rooms with fireplaces, and a game room. Outdoors: firepit with Muskoka chairs, gazebo with sofas, and west-facing sunsets. Perfect for Christmas gatherings, ice fishing trips, or group getaways year-round.