Vacation rentals with a pool in Orillia

Find and book unique homes with a pool on Airbnb

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Popular amenities for Orillia 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 stars5 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, 25 reviews

Cute and Cozy House

MartinRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Shanty Bay
4.89 out of 5 average rating, 63 reviews

King Bed, Pool, Gym, Ravine View, Your Getaway!

ElizabethRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Port Perry
4.93 out of 5 average rating, 218 reviews

Home away from home with a hot tub and pool

LornaRating, 5 stars3 days ago
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.
Guest favourite
Home in Beaverton
4.88 out of 5 average rating, 41 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

AlyssaRating, 5 stars1 month ago
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.
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 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.
Guest favourite
Home in Sebright
5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

AaronRating, 5 stars8 months ago
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.
Guest favourite
Home in Midhurst
5 out of 5 average rating, 8 reviews

Modern Farmhouse-luxe&comfort

YooraRating, 5 stars1 month ago
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

Superhost
Condo in Innisfil
4.82 out of 5 average rating, 471 reviews

Lovely 2-bedroom at Friday Harbour

ChadRating, 5 stars4 days ago
Great quiet getaway. Lots of things to see and do, plenty of room to walk and scooter or bike
Top guest favourite
Condo in Innisfil
5 out of 5 average rating, 62 reviews

FH Aquarius Bldg: Modern 2BR/2B Condo

CristinaRating, 5 stars1 month ago
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.
Guest favourite
Condo in Innisfil
4.9 out of 5 average rating, 201 reviews

Beautifully Furnished New Condo at Friday Harbour

NicoleRating, 5 stars2 months ago
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!
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 Innisfil
4.93 out of 5 average rating, 109 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

ZoyaRating, 5 stars3 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.
Superhost
Condo in Shanty Bay
5 out of 5 average rating, 4 reviews

Lux 4bd 2bath 1400 sqft Condo

SandyRating, 5 stars7 months ago
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!!
Guest favourite
Condo in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars10 months ago
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

Destinations to explore

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