Vacation 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

Top guest favourite
Home in Mono
4.97 out of 5 average rating, 38 reviews

Country Family Getaway with Pool and Trails

Cory & GinetteRating, 5 stars4 months ago
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!
Guest favourite
Home in Orillia
4.96 out of 5 average rating, 24 reviews

Cute and Cozy House

PatrickRating, 5 stars1 week ago
Anzhelika was a great host…easy to reach and communicate with. Her clear instructions made for an easy self check-in and great stay. The house was clean, updated and nice. Beds were comfortable and everything in the house worked. Location was near the city center on a quiet street. I would recommend this listing and would stay again if in the area.
Superhost
Home in The Blue Mountains
4.82 out of 5 average rating, 49 reviews

Spacious Chalet close to Ski resort. Pet friendly!

RobRating, 5 stars3 weeks ago
Excellent stay. Thanks for the home for the weekend.
Guest favourite
Home in Shanty Bay
4.88 out of 5 average rating, 60 reviews

King Bed, Pool, Ravine View, Near Ski Hills

ChristianaRating, 5 stars2 weeks ago
The place was perfect for my family of 3. It’s super close to Horseshoe Valley for snow tubbing and skiing. There’s a nordic spa close by that we’ll check out next time. We went a couple of times to Barrie. It’s such a lovely town. I highly recommend and we will certainly come back.
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 104 reviews

Spacious 4BR Snowbridge Home with Shuttle Access

AleksandarRating, 5 stars4 weeks ago
Very nice and spacious home with plenty of room for a large group to spread out. Loved the open concept kitchen and dining area and felt plenty close to Blue Mountain village and skiing.
Guest favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 191 reviews

Serene mountainside home View/Shuttle Bus/Pool

NikoleRating, 5 stars2 weeks ago
Our family loved our stay here. Great location, short drive to the village. My little kids really enjoyed the basement. Brendan was amazing and very helpful at all times.
Superhost
Home in Mono
4.76 out of 5 average rating, 17 reviews

Custom home that feels like the Spa

NickRating, 5 stars3 months ago
Great place to stay and very the host was awesome. Exactly as described.
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars2 months ago
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.

Condo rentals with a pool

Guest favourite
Condo in The Blue Mountains
4.85 out of 5 average rating, 141 reviews

Large, luxury, upper floor condo, steps to Village

MatthewRating, 5 stars3 months ago
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.
Guest favourite
Condo in The Blue Mountains
4.91 out of 5 average rating, 110 reviews

The Fairway Chalet

SathishRating, 5 stars2 weeks ago
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.
Superhost
Condo in The Blue Mountains
4.86 out of 5 average rating, 242 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

AndreaRating, 5 stars3 weeks ago
Everything good with the place, good communication with the host, 6 min drive to the village, we enjoyed the place a lot.
Guest favourite
Condo in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars6 months ago
Kevin was a responsive and friendly host, and his place is clean and comfortable and very close to Friday Harbour. We loved the balcony for breakfast and coffee, and the condo itself was full of friendly folks. We can't wait to go back sometime!
Superhost
Condo in Innisfil
4.91 out of 5 average rating, 139 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

LoriRating, 5 stars1 month ago
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).
Guest favourite
Condo in Blue Mountains
4.92 out of 5 average rating, 334 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

MeeghanRating, 5 stars1 week ago
Great place, close to the hill!
Guest favourite
Condo in Innisfil
4.93 out of 5 average rating, 109 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

ZoyaRating, 5 stars2 months ago
Apartment was even beyond our expectations. It was the most amazing place we have ever rented on New Year holidays. There were 6 people and the place was big and comfortable enough for everybody. Moreover, the apartment was extremely clean and had everything in it to live for short or long terms without any issues. The apartment is located in Friday Harbour which is the perfect place to live in. There are lots of shops, restaurants, a beautiful marina, pool , beach club nearby. We also went for skiing to Horseshoe resort, which took us approx 30 minutes to get there. Shai is a wonderful host, he was in touch during the entire period of our stay in his apartment. He left us a bottle of wine and chocolates as a present, it was so cute. Thank you so much for your attention and care. We will definitely rent your apartment again.
Guest favourite
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, Sleeps 4

SoniaRating, 5 stars6 months ago
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

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