House holiday rentals in Simcoe County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Simcoe County

House rentals with a pool

Guest favourite
Home in Utopia
4.87 out of 5 average rating, 47 reviews

Serene Escape: A Nature Getaway

DonnaRating, 5 stars3 weeks ago
I rented the villa for a group of 16 ladies for a golf getaway. The owners are excellent to communicate with and responded immediately to any questions or issues we had during and before our stay. The villa was spacious and well equipped with dishes ect to accommodate a large group. Beds comfortable. Unfortunately due to the weather the pool was not opened but some enjoyed the hot tub. Grounds looked like the would be very nice but again due to weather grounds we’re not manicured and grass has not been cut. Would definitely book again and hopefully next time enjoy the outdoor area. Thks for having us
Superhost
Home in The Blue Mountains
4.89 out of 5 average rating, 225 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

PamelaRating, 5 stars3 weeks ago
Visited with 4 couples for a few nights away. Beautiful location. Would recommend
Guest favourite
Home in Innisfil
4.92 out of 5 average rating, 48 reviews

2 Bd Boardwalk Condo Patio Oasis

DavidRating, 5 stars1 week ago
Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan
Guest favourite
Home in Barrie
4.93 out of 5 average rating, 94 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

DianeRating, 5 stars5 days ago
This house was perfect for our large group: for couples and a baby. Having the pool was a bonus that we really appreciated in the warm weather. The kitchen was extremely well equipped, and there were enough linens as well as pool towels for us all. There was plenty of space for everybody as the rooms were all quite large, particularly the master bedroom. The house were incredibly accommodating when we realized after checkout that we had left a couple of items behind. They were able to make arrangements for us to retrieve them several days later back in Toronto! I definitely can recommend this house.
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 106 reviews

Blue Mountain Retreat w/ Pool + Village Shuttle

AlanaRating, 5 stars1 month ago
We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.
Guest favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 196 reviews

Pool Open / Serene mountainside home View/Shuttle

TimRating, 5 stars1 month ago
We had a wonderful stay with a family of four including 18 year old teen boys and two dogs. The boys enjoyed the pool table and great tv's while my wife and I enjoyed the great walking and quiet surroundings. It was also easy to have our well trained dogs with us in this location which was wonderful. Thank you Brendan for the terrific stay and allowing us to change our reservation when our plans changed with ease.
Guest favourite
Home in East Gwillimbury
5 out of 5 average rating, 5 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

AbdulmalikRating, 5 stars1 month ago
This place is the perfect getaway for anyone looking to relax and enjoy quality time with family and friends. Surrounded by beautiful nature and fresh air, it offers a peaceful, private setting that’s ideal for both adventure and quiet moments. I highly recommend it to anyone seeking a refreshing escape.
Guest favourite
Home in Elmvale
4.89 out of 5 average rating, 19 reviews

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago
We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

Weekly house rentals

Guest favourite
Home in Barrie
4.96 out of 5 average rating, 50 reviews

Cozy Barrie Getaway ①: Private Clean New Build 3BR

KimberleyRating, 5 stars6 days ago
This place was very cute and cozy. The only downside was that there is no kitchen table. There is an island but as people who like to play board games, it would be nice to have a table. The place was very clean and had everything we needed. The host was very clear on her expectations and was easy to communicate with. 5stars would recommend.
Superhost
Home in Barrie
4.87 out of 5 average rating, 85 reviews

Suite close to Barrie Waterfront

TonyaRating, 5 stars2 weeks ago
Very beautiful apartment for a quick overnight stay. me and my daughter's enjoyed the proximity of the lake and restaurants
Guest favourite
Home in Minesing
4.89 out of 5 average rating, 79 reviews

14 Guest Retreat- 4BR/4BA Near Spas, Golf &Ski Fun

BrendaRating, 5 stars4 days ago
We were attending a family reunion, in the area and found Clair's place, for our home base for the weekend. It is a beautiful home and we felt comfortable and at home right away. Everything thing we needed was available and Clair was available to help us in any way. We hope to book this home again.
Top guest favourite
Home in Innisfil
5 out of 5 average rating, 47 reviews

Modern Boho Beach Retreat

RobertoRating, 5 stars1 month ago
This was hands down the cleanest Airbnb I’ve ever stayed in, spotless from top to bottom. Everything was incredibly neat, well-organized, and thoughtfully labeled with clear instructions, which made our stay seamless and stress-free. Mary truly went above and beyond in every way. She was super responsive when we had questions about local fishing tackle shops, and her attention to detail in the home was amazing. She left us a selection of teas, snacks, travel-sized lotion and hand sanitizer, and other small touches that made the whole place feel like a cozy hotel retreat. The neighborhood was peaceful and within easy walking distance of the lake a perfect location to unwind. Would absolutely recommend this stay to anyone looking for comfort, cleanliness, and a caring host.
Guest favourite
Home in New Tecumseth
5 out of 5 average rating, 13 reviews

HomeSweetHome!

VanessaRating, 5 stars1 week ago
This is the second time I stayed at Allison’s place and it is a lovely spot. The house is clean and comfortable and the kitchen well equipped. It is a perfect home away from home.
Guest favourite
Home in East Gwillimbury
4.9 out of 5 average rating, 20 reviews

Bright & Clean One Bdrm Aprt

RajaRating, 5 starstoday
very happy with the host, place and communication. will be back.
Top guest favourite
Home in Port McNicoll
5 out of 5 average rating, 27 reviews

Beautiful Home in Port McNicholl

ShayanRating, 5 stars1 week ago
Our stay at Keegan’s place was great. The cottage is beautiful and exactly as advertised. It had everything we needed and so much more - including board games etc. Keegan was also very responsive. Highly recommend to anyone for a peaceful weekend getaway!
Guest favourite
Home in Collingwood
4.95 out of 5 average rating, 74 reviews

Private Collingwood Home, with acreage & sauna

CoryRating, 5 stars1 week ago
Erics place was great for the weekend. Just outside of town to keep it a quiet place but close enough so you could go explore collingwood. Sauna is a great addition. Place was clean and had everything you needed for a comfortable stay.

Private house rentals

Guest favourite
Home in Innisfil
4.91 out of 5 average rating, 47 reviews

Summer Deals! Modern & Cozy, 4 Season Cottage!

KylieRating, 5 stars1 month ago
First cottage trip with friends this summer. Stayed 3 nights and had a blast. Clint was responsive and gave us great recommendations for activities/food around the area. We were able to have a great time cooking meals with the already provided cookware, utensils, bonfire (s’mores) etc. Utilized the big TV for movies, Nintendo Switch games, and music. If you’re interested in a clean mix between cottage vibes and homey this is the right place to pick. Would come back again. Aside from staying in we visited Friday Harbour: okay boardwalk (not much to do but to walk around), trail was nice.
Guest favourite
Home in Georgina
4.96 out of 5 average rating, 26 reviews

PoolTable 8MinsToLake PingPong Foosball King Beds

SwanaRating, 5 stars3 weeks ago
Mariam was a great host - we thoroughly enjoyed our stay. House was beautifully furnished and had lots of games available for us. Kitchen was very spacious and bedding was comfortable. We will definitely come back!
Guest favourite
Home in Collingwood
4.88 out of 5 average rating, 56 reviews

Blue Mountain Home

DeanRating, 5 stars5 days ago
We stayed at Dianna’s place while we were in Collingwood and the accommodate was even better than the photos! Her place had everything we needed and more. We only stayed a couple nights but it’s set up for long term stays as well. The location was 5 minutes from the water and a 6 minute drive to the downtown core. I would recommend this spot to anyone travelling to Collingwood.
Guest favourite
Home in Barrie
5 out of 5 average rating, 14 reviews

Beautiful Family Friendly Renovated Barrie Home

CarolRating, 5 stars1 month ago
The home exceeded our expectations, comfortable beds and linens, all the necessities and Adam was a personable and attentive host. We'd love to come back!
Guest favourite
Home in Midland
4.88 out of 5 average rating, 67 reviews

Close to Hospital and school 4 bedroom bungalow

MikeRating, 5 stars1 month ago
Our stay at this residence was truly exceptional. The property was impeccably clean and well-maintained, providing a comfortable and welcoming environment throughout our visit. The host was exceedingly courteous and readily available to address any inquiries or concerns, demonstrating a high level of hospitality. I would not hesitate to recommend this accommodation, and I am pleased to report that all of my companions were equally satisfied with their experience.
Guest favourite
Home in Clearview
4.93 out of 5 average rating, 15 reviews

New, Modern, Close to Wasaga Beach & Blue Mountain

StephanieRating, 5 stars1 week ago
Jamie’s place is charming and very well kept! Absolutely loved the fact that there’s a farmers field directly behind his house so that gave some additional privacy that isn’t there when an Airbnb home has a small subd backyard and then backs onto another home(s). Jamie was easy to deal with and was always responsive.
Top guest favourite
Home in Innisfil
5 out of 5 average rating, 48 reviews

Luxurious Lake House for Family Stays

LindseyRating, 5 stars1 week ago
What a dream location for our family to spend a week of relaxation and fun! The home was as beautiful in person as it was in the photos, and Paola was a lovely host. l Every last detail was thought of and truly made for such a memorable stay. We hope to return in the future!
Guest favourite
Home in Orillia
4.87 out of 5 average rating, 15 reviews

Upper Shadow Creek Haven - Waterfront

MarceloRating, 5 stars1 month ago
we had a wonderful stay. squeaky clean,stylish host was very accommodating .defiinetly would stay again.

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