Vacation rentals with a kayak in Georgina

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Top-rated kayak rentals in Georgina

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Guest favorite

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.

Condo in Innisfil

4.85 out of 5 average rating, 186 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

This Black Cherry model condo is the most sought after layout at Friday harbour, featuring a spacious-well-designed kitchen, living room and balcony area with two bedrooms and two bathrooms ideal for families, couples, or solo travellers. Enjoy comfortable sleeping with a king bed in the master bedroom also featuring an ensuite bath and walking closet, and a Queen bed in the second bedroom. Enjoy a view of the beautiful landscaped courtyard out to the marina, while lounging or eating outside.

Superhost

Cottage in Georgina

4.86 out of 5 average rating, 153 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.

Top 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

4.95 out of 5 average rating, 111 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!

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, 158 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

A pathway leads from a stone staircase to the entrance of a cozy cottage. Lush greenery and potted plants are visible alongside the well-maintained path. The lake shimmers beyond the cottage, reflecting the blue sky and offering a peaceful lakeside view.

Home in Nestleton Station

4.99 out of 5 average rating, 131 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 Georgina

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.

Top guest favorite

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, 129 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.

Guest favorite

The property features a spacious lawn bordered by trees, with a rustic cottage visible in the background. A 500 sq ft dock extends into the lake, equipped with seating. A fire pit area is set up on the grassy shoreline, inviting relaxation and outdoor gatherings.

Cottage in Minden

4.92 out of 5 average rating, 259 reviews

Dog-friendly Lakefront Cottage w/ Hot Tub + WiFi

Relax and unwind at South Lake! Located less than 10 minutes away from the town of Minden, you'll love swimming off the 500 sq ft dock, exploring by canoe and kayak, all the best lawn games, stunning sunsets from the new fire pit, and a sky full of constellations. Perfect for families or friends to enjoy all of the comforts of a modern cottage without missing rustic charm. Cozy up by the propane fireplace and play board games or watch movies. High-speed internet is remote work-friendly!

Guest favorite

A wooden dock extends into a calm lake, reflecting fluffy white clouds and blue skies. Lush greenery is visible along the shoreline, creating a serene natural backdrop.

Cottage in Kawartha Lakes

4.94 out of 5 average rating, 126 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, updated bathroom, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

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

4.91 out of 5 average rating, 105 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

The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.

Guesthouse in Port Perry

5 out of 5 average rating, 107 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 modern cottage is visible at the top of a sloping hill, framed by vibrant greenery. A wide set of wooden stairs leads from the dock area up to the cottage. Various watercraft, including kayaks and a canoe, are neatly arranged on the dock.

Cottage in Torrance

4.97 out of 5 average rating, 232 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 2 Minimum 6 nights with a Sunday check in.