Vacation rentals with a kayak in Regional Municipality of York

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Regional Municipality of York

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Guest favorite

Bungalow in Georgina

5.0 out of 5 average rating, 7 reviews

Sunset Shores Lakehouse w/Hot Tub

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

Guest favorite

Cottage in Georgina

4.97 out of 5 average rating, 58 reviews

Resort-Style Luxury Waterfront Cottage

Escape to Unforgettable Luxury at Our Waterfront Family Cottage on Simcoe, Just 80 KM from Toronto. Experience Breathtaking Sunsets and Sunrises from the Comfort of the Living Room and Loft. Relax on the Pristine Beach with Calm Waist-Deep sandy Waters, Right in Our Backyard. Take Advantage of the Patio, BBQ, Bar, Lounge , Kayak &Tubing for Endless Fun. Enjoy Comfort & Convenience with a Fully Equipped Kitchen, 3 Bedrooms, 2 Bathrooms & Space for Up to 8 Guests. Secure Your Dream Getaway Today!

Guest favorite

Apartment in Innisfil

5.0 out of 5 average rating, 12 reviews

Fantastic 1 Bdrm With A View.

Kick back and relax in this calm, stylish space. It's the perfect singles or couples retreat, not meant or set-up for young children. Relax in the comfort of a great mattress & soft & silky bed sheets. Enjoy the Southern exposure with the courtyard view including the pool & hot tub. So much to see & do at Friday Harbour with Restaurants, Shops, Marina, Beach, Water Activities, Golf, Music & Entertainment. Come for a weekend or a longer term, enjoy everything because Everyday Feels Like Friday.

Guest favorite

Condo in Innisfil

5.0 out of 5 average rating, 10 reviews

Chic Retreat-@The Harbour 5* Resort-King Size Bed

Getaway in one of the most exclusive resorts in INNISFIL. Four Season- 5 Star has panoramic views- on Lake Simcoe Amenities - from fine dining- live entertainment on Pier - Beach /Lake Club - Pool - Hot tub (seasonal) -Water sports/ boat rentals - retail - 7 restaurants - Pet Store + Pottery Craft Studio. Condo comes equipped with modern appliances/dinnerware- Comfortable King Size bed - Queen sleeper sofa -high speed internet - TV's. Enjoy your coffee or evening cocktails on private balcony.

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 112 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

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!

Guest favorite

Condo in Innisfil

4.84 out of 5 average rating, 172 reviews

Marina view at Friday Harbor 2bdm/2bth Pool option

Friday Harbour is a brand new all season resort just 1 hour and 15 minutes from Toronto. A perfect getaway without the long drive. Airbnb guests can now purchase a pass for the beach club pool! This Airbnb is an eight hundred square foot condo all newly furnished with king bed in master bedroom with ensuite bathroom, Queen bed in guest bedroom. Enjoy 65” Samsung Smart TV or sitting on the huge deck overlooking the marina and island homes. Board walk to beach, this place is amazing!

Guest favorite

Cottage in Georgina

4.99 out of 5 average rating, 136 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

Cottage in Innisfil

4.98 out of 5 average rating, 123 reviews

Charming waterfront cottage on Lake Simcoe

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

Guest favorite

Condo in Innisfil

4.95 out of 5 average rating, 57 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

Book your accommodations with us & enjoy the prestigious FH Resort. FH wasn’t designed to be a place. It was designed to be a destination. Were you can unwind, disconnect & reconnect all your senses with the healing powers of the forest & beautiful sunsets, truly feel relaxed. Whether you come to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of ways to enjoy your days."

Guest favorite

Cottage in Richmond Hill

4.95 out of 5 average rating, 129 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Guest favorite

Cottage in Georgina

4.9 out of 5 average rating, 241 reviews

Beach House-S/W Exposure! Hot Tub Sandy Water!

Location, Location, Location! S/W Exposure! firepit, hot tub, west-facing sunset views, fishing, swimming, boating, and nearby amenities. In winter, it transforms into a winter wonderland, perfect for ice fishing and snowmobiling. New renovated 4-seasons retreat. Less than an hour from the GTA. This lakeside haven on Prestigious Cooks Bay provides the ideal getaway. Enjoy a rejuvenating experience with a *** Don't miss out on this incredible opportunity ***

Guest favorite

Home in Innisfil

5.0 out of 5 average rating, 15 reviews

Luxury home with pickleball!

Bright, modern home on a quiet dead-end street, steps away from Friday Harbour Resort - restaurants, beach, shops, sailing lessons, watercraft rentals, and more! Enjoy a phenomenally equipped chef's kitchen, large living room with home audio system, dining room, home theatre, gym. Outside, enjoy the regulation pickleball court, Jacuzzi tub, expansive deck with multiple shaded/sunny seating options, gas barbeque.