
Vacation rentals with a pool in Orillia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Orillia
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Orillia 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
Anzhelika was a great host. She was very responsive and easy to communicate with. Her place was very nice and convenient for us as we were going to a show at Casino Rama. Would love to come back in the summer to enjoy the pool.

King Bed, Pool, Gym, Ravine View, Your Getaway!
My boyfriend and I had a wonderful stay at Candace and Montu’s townhome. The unit was clean and as described. The hosts were super responsive and proactive with providing instructions for check in and check out. Perfect distance to the Vetta Nordic spa which we enjoyed. 10/10 recommend staying here.

Home away from home with a hot tub and pool
Had a great time at Angie's place! Everything was very clear, clean and easy—instructions were left out and amenities were provided. The hot tub was a great bonus to the weekend. We even had a delayed car picking us up, and Angie was very accommodating and understanding about letting us stay slightly longer while waiting for its arrival.

Luxury Family Home Indoor Pool Hot Tub Lake Access
The place was beautiful and the pool was perfect for a winter get-away. They were super responsive the entire time and check-in/out was super easy.

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths
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.

All Season Waterfront Retreat with Pool & Hot Tub
Gary & Mina were excellent hosts. They greeted us for check in and where very accommodating. Any questions we had were quickly answered via the AirBNB app. The house was full of character and had lots of things to do indoors and outdoors. The kitchen was well stocked with supplies, utensils and kitchen wares. There was a washer/dryer centrally located which was great for towels and the Weber BBQ was in top notch condition. Water toys well maintained (2 kayaks, 1 paddle board, 1 canoe and 1 paddle boat). Pool and hot tub worked great, which was a must for our cottage getaway.

Modern Farmhouse-luxe&comfort
I recently had a pleasure of staying at this Airbnb, and I couldn’t be more satisfied with my experience. The space was clean, spacious and tidy, making it the perfect retreat for my getaway with my friends. From the moment I arrived, I was impressed by how well-maintained the property was. The cleanliness truly stood out, and it was evident that the host take great pride in providing a welcoming environment. The spacious layout allowed for plenty of room to relax and unwind, and I appreciated the thoughtful touches throughout the home. Overall, I highly recommend this Airbnb to anyone looking for a comfortable and enjoyable stay with a large group. I will definitely be returning in the future.
Condo rentals with a pool

Lovely 2-bedroom at Friday Harbour
Great quiet getaway. Lots of things to see and do, plenty of room to walk and scooter or bike

FH Aquarius Bldg: Modern 2BR/2B Condo
Beautiful unit with fully equipped kitchen & everything you need to feel right at home. Beds are comfortable, we were 2 people but it would fit 4 comfortably. Would definitely be back.

Beautifully Furnished New Condo at Friday Harbour
We had a great stay! The place was incredibly clean, and had everything we needed and more. We felt right at home, and communication with the host was excellent! Everything was easy to find. There was an awful snow storm over the weekend that we stayed, but the place was so cozy and clean, we were happy to stay in and binge watch some Netflix :) I can’t recommend Jennifer Nicole’s place enough!

Friday Harbor Upscale 1Bed+Sofabed+Pool Option
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!

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

Exceptional 2+1 ground floor condo @Friday Harbour
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.

Lux 4bd 2bath 1400 sqft Condo
This Lux 4bd Condo was exactly as described. We had a wonderful time having both units with 6 ladies. The place is beautifully decorated and we found everything we needed. Jordan was very responsive to any of our questions and always so helpful! The back deck was so peaceful looking out into the woods. It was a beautiful 5 min walk to the Vetta Spa which we also highly recommend!!

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!
Quick stats about vacation rentals with a pool in Orillia
Total rentals
10 properties
Nightly prices starting at
$111 CAD before taxes and fees
Total number of reviews
370 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Costco Wholesale, Mariposa Market, and Canadian Tire
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Georgian Bay Islands National Park
- Gull Lake
- Muskoka Lakes Golf and Country Club
- Devil's Glen Country Club
- Lakeridge Ski Resort
- Lake Joseph Golf Club
- Muskoka Bay Resort
- Alpine Ski Club
- Angus Glen Golf Club
- Summit Golf & Country Club
- South Muskoka Curling and Golf Club
- Toronto Ski Club
- Rocky Crest Golf Club
- The Georgian Peaks Club
- National Pines Golf Club
- Shanty Bay Golf Club
- Bushwood Golf Club
- King Valley Golf Club