
Vacation rentals with a pool in Simcoe County
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Top-rated rentals with a pool in Simcoe County
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Popular amenities for Simcoe County rentals with a pool
House rentals with a pool

Country Family Getaway with Pool and Trails
We had an amazing stay! Communication with the hosts was quick, and they were very attentive to all our needs, ensuring we had everything we required. The house was perfectly suited for our group of 8, offering plenty of space and comfort. The property itself is beautiful, with easy access to scenic walks and hikes right on the grounds. Plus, it was just a short drive to Hockley Valley, where we attended our event. This place was ideal for our weekend getaway, and we’d definitely stay here again!

Cute and Cozy House
After being displaced from our home after damage from severe weather we were so fortunate to find this location. The house accommodated our family of 4 with pets for nearly a month without any issues. The kitchen is well equipped, bathrooms are well finished, bedrooms were comfortable and the location was very clean. The backyard is a beautiful and relatively private space hidden within a 15 minute walk to the downtown restaurants or the beach area. Anzhelika is an excellent host who was very responsive when needed, provided clear instructions and ample privacy. We would happily recommend this location to friends and family attending the area for events.

Serene Escape: A Nature Getaway
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

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King
Had a group of 10 stay here very comfortably with multiple options , house was clean and organized. Brendan was very helpful and kind and made us feel right at home. Blue mountain and surrounding area was awesome had lots of activities and restaurants and the golf course was amazing. Thank you again for this great experience!

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
Jerry was very accommodating and fixed any issues promptly. The place is very nice and comfortable for multiple people ….there is space for all. Kitchen has everything you need to cook. Would stay here again for sure. Thank you Jerry,

4BR Family Home w/ Pool Access + Village Shuttle
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.

Pool Open / Serene mountainside home View/Shuttle
Thank you Brendan for a wonderful stay in your beautifully decorated and very clean townhouse in Blue Mountain!! We had a wonderful time celebrating my Mom’s 80th birthday! It felt very comfortable and spacious for our small group. The shuttle to and from the village was on time and friendly - we also walked there too during the day. Excellent customer service and amenities. I highly recommend. Thanks again!

Private cottage heated pool/HotTub/Games 20 Acre
Stayed here for a few days for a work retreat. Place was great for what we needed. Tons of space and a very pretty location on a quiet country road. A few issues with the amenities - bbq didn’t work well, the hot tub was pretty green, and the dishwasher was temperamental, but when we reached out, they sent someone over to address it right away. Overall, it was exactly what we needed and we had a great stay - would definitely recommend/come back!
Condo rentals with a pool

Large, luxury, upper floor condo, steps to Village
Excellent place by a fantastic host. The place was clean, well located and has everything you would need such as kitchen utensils, games + TV, and plenty of clean quality towels. Ulana and Amir were also very friendly and responsive. We enjoyed our stay a lot.

The Fairway Chalet
From the initial booking confirmation to the final checkout, the hosts were absolutely outstanding! They provided clear and detailed directions to the property, and the space was impeccably clean upon our arrival. The rooms were cozy and well-maintained, and the kids especially loved their room. Overall, it was a delightful and memorable stay at Blue Mountain.

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft
Rosa’s was exactly as advertised. It was lovely and quiet and perfect for our trip to collingwood with our dog. We would definitely stay again!

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!

2 Bedroom, 2 Level Condo on Blue Mountain!
Great place and fantastic hosts! We truly enjoyed our stay here. The sound of the stream was very relaxing when we sat out in the patio. The upper level has a nice view of the lake too!

Friday Harbour Luxury Condo Escape, Sleeps 4
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Private Backyard/Shuttle/Pool/10min walk 2 village
Elyse’s place is lovely! It looks just like the pictures. It was cozy and comfortable during a huge snowstorm. The kitchen is very well quipped. Neighborhood is very pretty and security was visible. Snow was cleared very quickly. Nice proximity to both Blue Mountain and Collingwood. Elyse is a welcoming and very responsive host. Would definitely stay again!
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- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Port Carling Golf & Country Club
- Mount St. Louis Moonstone
- Horseshoe Resort
- Osler Bluff Ski Club
- Snow Valley Ski Resort
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- Lake Joseph Golf Club
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- Beaver Valley Ski Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- Angus Glen Golf Club
- Devil's Glen Country Club
- Caledon Country Club
- Alpine Ski Club
- Goodwood golf club
- National Pines Golf Club
- Barrie Country Club
- Granite Golf Club
- Dagmar Ski Resort
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