Beachfront vacation rentals in Regional Municipality of York

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Regional Municipality of York

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Innisfil

4.93 out of 5 average rating, 15 reviews

The Penthouse at Friday Harbour

Relax in this calm, stylish space. Our 1 Bedroom Suite has an abundance of Natural Light beaming in. You will experience Serene Sunrises and Sunsets from the Top Floor Balcony overlooking the courtyard pool, fire pit and Year round Hot tub. The relaxing adjustable bed and couch adds to a dream space to curl up or watch a movie after dinner at one of the many wonderful restaurants within Friday Harbour. A 3 Day minimum is a Friday Harbour requirement ; avoid problems renting with shorter terms.

Jun 2 – 9

G$23,535 GYD per night

Guest favorite

Loft in Barrie

4.95 out of 5 average rating, 190 reviews

The Penthouse | Luxury at the Lake

Live the good life at 'The Penthouse' on Lake Simcoe. This is a luxurious and historical loft with stunning views of the bay. It's beautiful, bright, clean and spacious - perfect for romance and adventure with friends. Steps to the sandy beach, waterfront trails and the heart of downtown. Enjoy a meal downstairs at the legendary 'Farmhouse Restaurant'. Perfect all-in-one wedding venue, room to get ready and a party downstairs. If you're looking to unwind or a night on the town, it's all yours!

Jul 28 – Aug 4

G$35,299 GYD per night

Guest favorite

Cottage in Georgina

4.96 out of 5 average rating, 57 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!

Sep 8 – 15

G$137,171 GYD per night

Guest favorite

Condo in Innisfil

4.97 out of 5 average rating, 111 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!

Sep 6 – 13

G$22,918 GYD per night

Guest favorite

Cottage in Innisfil

4.9 out of 5 average rating, 290 reviews

Crystal Beach Cottage & Spa

Tranquil & serene lakefront cottage with breathtaking views! This cottage fronts on the East side & faces West for a mesmerizing sunrise & sunset. A few steps to the lake for a dip in the lake, sun bathing, paddle boarding or a stroll up Innisfil Beach Park for exercise. A custom outdoor steel fire place and an all season hot tub awaits you at any moment to loosen up those muscles & release tension or kick back in the sauna to sooth the mind, body & soul. A wonderful experience awaits you!

Jun 5 – 12

G$79,678 GYD per night

Guest favorite

Condo in Innisfil

5.0 out of 5 average rating, 23 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.

Jun 6 – 13

G$25,123 GYD per night

Superhost

Condo in Innisfil

4.95 out of 5 average rating, 183 reviews

Designer Condo with beautiful harbour view.

Unique top floor. Rare views where every room overlooks the harbour. Professionally designed with new stylish furnishings. Ideal for those who like a little sophistication while spending time at the lake. Enjoy going out to eat every night or make a meal and curl up and relax in the stylish living room, or a combination of both! Friday Harbour is a resort with beautiful walking trails, cafes, and restaurants, and a perfect get-away that celebrates the seasons with exiting activities.

Sep 11 – 18

G$43,789 GYD per night

Guest favorite

Cottage in Innisfil

4.91 out of 5 average rating, 128 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

.🧘 Relaxing, Quiet, waterfront property with stunning nature. 🧖‍♀️ Experience a private Spa with year round new sauna & new hot tub and amazing view 🤫 A peaceful oasis for families. Please describe your family before requesting to book. Max 6 guests incl children. Absolutely no events, parties, noise allowed. Not for a group of friends 🏖50’x302’ lot, private dock, gazebo 👩🏻‍💻65” smart 4K UHD TV, fast / reliable internet, LCD fridge, filtered water, all high tech.

Jan 14 – 21

G$81,469 GYD per night

Guest favorite

Condo in Innisfil

5.0 out of 5 average rating, 71 reviews

Boho by the Bay

BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." New, this year, the Resort offers passes to Airbnb guests . There are fees for the passes which can be obtained at the 'Welcome Centre'. Please indicate if you would like to purchase passes as an email confirming that you are an Airbnb guest is required.

Jul 20 – 27

G$16,706 GYD per night

Superhost

Cottage in Innisfil

4.92 out of 5 average rating, 37 reviews

Lake Side Manor With Games Room

A Family Retreat Awaits - Perfect for Multi-Generational Families or Multiple Families Travelling Together! Relax by the water enjoying the walk-in sandy beach. The kids will love the slide off the dock and the trampoline! On a rainy day, the enormous games room with ping pong, air hockey and foosball will be your favourite hangout! Just bring yourselves! We offer appropriate toys kids of all ages, high quality baby equipment and baby proofing and pet packages.

May 4 – 11

G$55,587 GYD per night

Guest favorite

Cottage in Georgina

4.9 out of 5 average rating, 239 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 ***

Mar 24 – 31

G$142,069 GYD per night

Guest favorite

Condo in Innisfil

4.96 out of 5 average rating, 94 reviews

Friday Harbour Luxury Condo, Sleeps 4

Escape to a modern, bright, luxurious, fully furnished 1 bedroom condo walkout balcony located in the beautiful Friday Harbour All Seasons Resort. Enjoy the autumn colours with a True resort feel. Spectacular golf, trails, beach, boating, biking & live music ++ Queen bed + pullout, sleeps 4. Two Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking our private pool, marina & beautiful sunset. 1 Free Parking, Electric BBQ, In-Suite Laundry

Sep 14 – 21

G$30,244 GYD per night