Holiday rentals with a pool in Simcoe County

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Simcoe County rentals with a pool

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 stars4 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, 226 reviews

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

KayeeRating, 5 stars2 weeks ago
Great stay at Blue Mountain. The kiddos really enjoyed the game room and the pool table. it was also super convenient to be able to schedule free shuttle to pick up and drop off to and from the village. Even if couldn't catch the shuttle it's only 20 min walk.
Guest favourite
Home in Innisfil
4.92 out of 5 average rating, 48 reviews

2 Bd Boardwalk Condo Patio Oasis

DavidRating, 5 stars2 weeks 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 stars1 week 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.
Superhost
Home in Minesing
4.75 out of 5 average rating, 8 reviews

Farm House Resort Stay Pool Hot Tub

MelissaRating, 5 stars10 months ago
The stay was amazing with family ! There was always lots to do lots of room for everyone ..pool and hot tub were wonderful it was nice to have both as an option ! Communication was on key Amanda answered right away there was no waiting on her that was nice ! If you forgot something behind it was available ( shampoo, spices, ect ) . Overall stay was amazing we are hoping to go back same time next year if available !

Condo rentals with a pool

Guest favourite
Condo in The Blue Mountains
4.98 out of 5 average rating, 159 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

JohnRating, 5 stars3 weeks ago
Our one night stay at Sabine’s was tremendous. The home is well appointed with plenty of space and easy walking distance to the village. Located in a second floor end unit, it’s a place you immediately feel comfortable in. There is a view of the slopes from the main room picture windows and a small deck area with muskoka chairs. There’s a sizeable fridge to store your beverages to drink while soaking up the views. There are two bedrooms on the main floor, and good sized master in the loft with king bed and en suite. Sabine was very communicative and left detailed instructions. Remote check in was a breeze. There is parking available. I would definitely recommend, and would definitely come back.
Top Guest favourite
Condo in The Blue Mountains
4.93 out of 5 average rating, 523 reviews

*Blue Mountain Village* Walk To Blue, Pool, HotTub

ChristineRating, 5 stars3 weeks ago
Great location, really close to the village, golf, trails and the Scandinave Spa. Condo unit is exactly as advertised with a comfy sofa to lunge on. Beds are comfortable and all linens and needed amenities were easy to find and use.
Guest favourite
Condo in The Blue Mountains
4.93 out of 5 average rating, 292 reviews

Cozy Studio Mountainside stay in Blue Mountains

EmmaRating, 5 stars1 week ago
Absolutely Wonderful Stay! I had an amazing stay at John and Kristi’s condo! From the moment I arrived, everything was spotless, cozy, and thoughtfully equipped with everything one could possibly need for a comfortable stay. The attention to detail made it feel like a home away from home. The pool and hot tub area were a real bonus—clean, relaxing, and perfect after a day of exploring. I definitely made the most of it! The location was also ideal, just a pleasant 10-minute walk to the village, which made it easy to enjoy the local shops, restaurants, and atmosphere without needing to drive. John and Kristi were fantastic hosts—friendly, responsive, and clearly committed to creating a great guest experience. I would absolutely stay here again and highly recommend it to anyone visiting the area!
Guest favourite
Condo in The Blue Mountains
4.94 out of 5 average rating, 301 reviews

Cozy & Charming Retreat at Blue Mountain

JimRating, 5 stars1 day ago
Clean and well appointed. Looked and felt brand new. Leo and Josie were excellent communicators and very helpful. A great place to stay. Highly recommend.
Superhost
Condo in Innisfil
4.91 out of 5 average rating, 142 reviews

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

AnisaRating, 5 stars1 month ago
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!
Guest favourite
Condo in Blue Mountains
4.92 out of 5 average rating, 344 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

BraydonRating, 5 stars1 week ago
This place was beautiful! As soon as we walked in, we felt at home. All the amenities listed were in the property and in good condition. Richard was very helpful and responsive when we had questions for him. There were extra pillows for people who sleep with more than just one lol. The ceiling fan in the loft really cooled down the place and kept the place at a good temperature. The area is also lovely, with a nearby tennis court on the resort. My friends and I spent most of our time there playing pickleball and tennis. Also, Blue Mountain village is about a 20 minute walk from the resort, so my friends and I went to visit at night. Overall, this was a lovely place to stay for the weekend and I would definitely come back again!
Guest favourite
Condo in The Blue Mountains
4.94 out of 5 average rating, 235 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

CarlyRating, 5 stars2 weeks ago
Great condo in a perfect location. The location is well stocked and has everything you could need. Walkable to restaurants and the village. Olga was a kind and responsive host. We wouldn’t hesitate to stay here again!
Guest favourite
Condo in Innisfil
4.88 out of 5 average rating, 215 reviews

Lake Simco penthouse at Friday Harbour resort

MopinaRating, 5 stars4 days ago
Such a beautiful place!! Anastasia was super responsive. Would definitely visit again

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Rentals with pools