Holiday rentals with outdoor seating in Simcoe County

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Simcoe County

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 195 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

16 – 23 Sept

$1,766 AUD total

Guest favourite

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!

9 – 16 Oct

$1,206 AUD total

Guest favourite

Condo in Innisfil

4.84 out of 5 average rating, 171 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!

23 – 30 Mar

$1,255 AUD total

Guest favourite

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

4 – 11 Mar

$1,933 AUD total

Guest favourite

Apartment in Wasaga Beach

4.95 out of 5 average rating, 339 reviews

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

8 – 15 Jan

$1,437 AUD total

Guest favourite

Dome in Hawkestone

4.94 out of 5 average rating, 241 reviews

Glen Oro Eco-Retreat Glamping Stargazer Dome

Leave the noise and rush of the modern world behind, unplug from your normal routine and immerse yourself in a beautiful old growth hardwood forest. Our Eco-Retreat focuses on providing a luxurious platform for you to stay in all the comforts of a boutique hotel amidst the raw and natural beauty of our Canadian wilderness. Here at Glen Oro we have over 200 acres of rolling fields and forests, horseback riding, hiking trails, and an incredible starry night sky.

13 – 20 Dec

$4,004 AUD total

Guest favourite

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

23 – 30 Oct

$2,197 AUD total

Guest favourite

Cottage in Torrance

4.97 out of 5 average rating, 196 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 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.

20 – 25 May

$1,293 AUD total

Guest favourite

Dome in East Gwillimbury

4.92 out of 5 average rating, 130 reviews

Deerleap Glamping Dome

Looking for a peaceful escape from the city? Our glamping dome offers just that, situated on 10 acres of picturesque land with trail, streams, and a stunning pond view. Perfect for a romantic retreat or a weekend getaway with the family, our dome is equipped with everything you need, from upscale sanitary to fast Wifi. Relax and enjoy the starry sky from the comfort of your bed, gather around the bonfire for s'mores , or explore nearby Lake Simcoe.

17 – 22 Nov

$1,616 AUD total

Guest favourite

Guest suite in Barrie

4.97 out of 5 average rating, 136 reviews

Cozy and Close to Everything!

This 600 square foot one bedroom lower level apartment is flooded with light from it's huge windows. Our totally private second suite features a separate entrance, full kitchen & laundry facilities, access to a large BBQ and full reign of the backyard. With access to fast wifi and Netflix you're sure to be connected and fully entertained.

6 – 13 June

$946 AUD total

Guest favourite

Tiny home in Waubaushene

4.97 out of 5 average rating, 292 reviews

Unique Tiny Home

This truly is a unique space with great attention placed on details. I design and build unique livable spaces catered to the individual needs of my clients. I invite you to come experience high quality living in a modern tiny home and experience sustainable, affordable living in just 280 square ft.

28 July – 4 Aug

$1,484 AUD total

Guest favourite

Guesthouse in Collingwood

4.93 out of 5 average rating, 117 reviews

The Little House on the Creek

Brand new accommodations. Enjoy a cozy, relaxing stay in a tiny home with all the amenities. 5 minutes to Blue Mountain Ski Resort and Village, Scandinave Spa, Scenic caves and downtown Collingwood. Or just sit back and enjoy outdoor fire and hot tub while viewing babbling stream.

4 – 11 Mar

$1,876 AUD total