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Beachfront vacation rentals in Kempenfelt Bay

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Kempenfelt Bay

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

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Cottage in Brechin

4.96 out of 5 average rating, 118 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.

Oct 22 – 29

G$41,770 GYD per night

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

Summer Getaway - 3 min walk to Beach, Clean & Cozy

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

Dec 27 – Jan 3

G$89,878 GYD per night

Loft in Barrie

4.95 out of 5 average rating, 191 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!

Oct 7 – 14

G$36,689 GYD per night

Apartment in Wasaga Beach

4.95 out of 5 average rating, 358 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

Oct 14 – 21

G$28,600 GYD per night

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!

Oct 9 – 16

G$22,542 GYD per night

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!

May 16 – 23

G$48,578 GYD per night

Home in Orillia

4.85 out of 5 average rating, 203 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

May 24 – 31

G$89,669 GYD per night

Condo in Innisfil

4.95 out of 5 average rating, 185 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.

Aug 27 – Sep 3

G$50,431 GYD per night

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.

Sep 21 – 28

G$105,406 GYD per night

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 229 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Oct 27 – Nov 3

G$36,697 GYD per night

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 ***

Apr 17 – 24

G$141,533 GYD per night

Cabin in Innisfil

4.9 out of 5 average rating, 316 reviews

Lake Simcoe Cottage & Hot Tub

Only 5 minutes walk to the beach with a panoramic view! Enjoy 2 bedroom cottage at Lake Simcoe all year round. HOT TUB, Natural Wood Fireplace, 65" TV with Netflix (Wi-Fi is fast), backyard facing the forest, front yard facing the conservation area. BBQ, fire pit, and table games will be waiting for you at our cottage. The famous Friday Harbour is only 5 minutes drive. Allandale Golf Course is 3 minutes drive INSTA: lake_simcoe_cottage

Jun 5 – 12

G$41,302 GYD per night

Vacation rentals for every style

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Popular amenities for Kempenfelt Bay beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Condo in Innisfil

4.77 out of 5 average rating, 143 reviews

2 Bdr Condo at Luxury Friday Habour Resort

Oct 23 – 30

G$27,528 GYD per night

Cottage in Innisfil

4.86 out of 5 average rating, 74 reviews

Hot Tub / BANYA / Sauna - True Cottage experience

Apr 11 – 18

G$35,365 GYD per night

Condo in Innisfil

4.95 out of 5 average rating, 57 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

Feb 20 – 27

G$36,941 GYD per night

Townhouse in Barrie

4.87 out of 5 average rating, 38 reviews

Full Townhouse - Trails, Lakes, Rinks & much more!

Jan 29 – Feb 5

G$24,396 GYD per night

Cottage in Georgina

4.96 out of 5 average rating, 57 reviews

Resort-Style Luxury Waterfront Cottage

Mar 31 – Apr 7

G$118,832 GYD per night

Cottage in Oro Station

4.92 out of 5 average rating, 36 reviews

Lake Simcoe south exposure lakefront with hot tub

Oct 25 – Nov 1

G$100,748 GYD per night

Home in Barrie

4.88 out of 5 average rating, 17 reviews

Lakeview 3-Bedroom Main level of home

Jul 1 – 8

G$61,125 GYD per night

Cottage in Innisfil

4.99 out of 5 average rating, 92 reviews

❤️ Charming Cottage/Lake View/10PPL/5BDR/3BATH

Aug 23 – 30

G$91,857 GYD per night

Beachfront home rentals with a pool

Bungalow in Orillia

4.87 out of 5 average rating, 207 reviews

Luxury, Spacious 4 bdrm Bungalow in South Muskoka

Feb 3 – 10

G$47,243 GYD per night

Townhouse in Wasaga Beach

4.9 out of 5 average rating, 147 reviews

Scenic WasagaBeach seasonal HeatedPool FireplaceAC

Feb 25 – Mar 4

G$55,386 GYD per night

Townhouse in Wasaga Beach

4.78 out of 5 average rating, 143 reviews

Bayfront Beach Resort 3AB/Wasaga Beach Front Pool

Jun 10 – 17

G$46,315 GYD per night

Condo in Innisfil

5.0 out of 5 average rating, 37 reviews

Upscale Spa Getaway w/Pool - Hot Tub & Sauna!

Apr 2 – 9

G$34,067 GYD per night

Condo in Innisfil

4.94 out of 5 average rating, 16 reviews

The Penthouse at Friday Harbour

Jun 4 – 11

G$23,447 GYD per night

Condo in Innisfil

4.96 out of 5 average rating, 94 reviews

Friday Harbour Luxury Condo, Sleeps 4

Sep 15 – 22

G$30,130 GYD per night

Condo in Innisfil

5.0 out of 5 average rating, 24 reviews

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

Jul 20 – 27

G$29,009 GYD per night

Condo in Innisfil

4.89 out of 5 average rating, 47 reviews

FH Harbour Flats 2BR 2BA- Every Day is Friday

Aug 17 – 24

G$37,507 GYD per night

Private beachfront home rentals

Cabin in Innisfil

4.92 out of 5 average rating, 78 reviews

Lake Simcoe Cabin, Innisfil, Ont

Dec 2 – 9

G$29,026 GYD per night

Condo in Innisfil

5.0 out of 5 average rating, 72 reviews

Boho by the Bay

Mar 24 – 31

G$15,507 GYD per night

Condo in Innisfil

4.96 out of 5 average rating, 26 reviews

Lakeside Studio Retreat at Friday Harbour Resort

May 21 – 28

G$19,359 GYD per night

Home in Barrie

4.97 out of 5 average rating, 32 reviews

Exclusive Lakefront House on Private Lake

Jul 23 – 30

G$66,165 GYD per night

Cottage in Innisfil

4.97 out of 5 average rating, 35 reviews

Friday Harbour Cottage Beach Kayak Firepit BBQ

May 22 – 29

G$94,796 GYD per night

Guest suite in Wasaga Beach

5.0 out of 5 average rating, 34 reviews

Corner Gem - Wasaga Beach

Oct 7 – 14

G$29,607 GYD per night

Condo in Innisfil

4.93 out of 5 average rating, 30 reviews

Beautiful gateway @ Four Seasons Resort, Innisfill

Jan 13 – 20

G$26,374 GYD per night

Cabin in Orillia

4.9 out of 5 average rating, 21 reviews

Family cottage just steps away from Lake Simcoe

Jun 14 – 21

G$62,854 GYD per night

Destinations to explore