Holiday rentals with a kayak in Regional Municipality of York

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Regional Municipality of York

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Innisfil

5 out of 5 average rating, 25 reviews

Blu Lake House *Dock *Game room *Pedal Boat *Kayak

Enjoy a peaceful two-story waterfront cottage with beach access. The perfect escape! Located an hour from Toronto. This cottage includes pedal boat, kayak, paddle board, inflatable rafts, volleyball net, basketball net, and swings facing lake view. Unwind with Netflix, or enjoy the game room, which includes a pool table, foosball, hockey, basketball, and Xbox 360. Local attractions such as the Gateway Casino, Cooks Bay Marina, Indy Go-Kart, Tanger Outlet, Local Eateries, Farmer Markets and more.

Guest favourite

Cottage in Innisfil

5 out of 5 average rating, 19 reviews

The Gingerbread Guest House

Take it easy at this unique and tranquil getaway. A short walk to the Belle Aire community beach where you can enjoy some sun, sand and Lake Simcoe. Enjoy a weekend away or a change in scenery to get away from the hustle of the city and is the perfect setting for longer-term or short stays. Enjoy the features in the chef-inspired custom cottage kitchen and refine your BBQ cooking skills on the backyard deck to impress your guests. This is a guest house & the owners live separately next door.

Guest favourite

Rental unit in Innisfil

5 out of 5 average rating, 28 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

Surround yourself with style in this standout & brand new space. Friday Harbour's Newest Addition. This 1 Bedroom 1 Bath unit with fantastic pool & hot tub views into the beautifully landscaped courtyard. Enjoy strolling the Promenade Boardwalk filled with Restaurants, shops, grocery, LCBO, Starbucks & more. Enjoy the views of the large marina landscaped with boats & jet ski's. The beach is serene and peaceful w/plenty of water activities to enjoy from paddle boards, kayaks, canoes & swimming.

Guest favourite

Condo in Innisfil

5 out of 5 average rating, 21 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 favourite

Condo in Innisfil

5 out of 5 average rating, 106 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!

Guest favourite

Condo in Innisfil

4.98 out of 5 average rating, 134 reviews

#TheFridayFlat: An Autumn Retreat to Unwind

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 favourite

Cottage in Georgina

4.99 out of 5 average rating, 148 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 favourite

Condo in Innisfil

4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/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 favourite

Home in Innisfil

4.98 out of 5 average rating, 127 reviews

Charming waterfront cottage on Lake Simcoe

Charming three bedroom cottage with 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, trampoline, basketball net, paddle boat, floating mat, kayaks, canoe, paddle board, pool table, foosball. fishing gear, life jackets

Guest favourite

Cottage in Georgina

4.98 out of 5 average rating, 80 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our resort-style waterfront cottage on Lake Simcoe, just 80 KM from Toronto! Enjoy breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters. The property features a patio, BBQ, bar, lounge, and activities like kayaking and tubing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for a perfect blend of relaxation and adventure!

Guest favourite

Cottage in Richmond Hill

4.94 out of 5 average rating, 141 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 favourite

Cottage in Georgina

4.9 out of 5 average rating, 259 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. *** Don't miss out on this incredible opportunity ***