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

Guest favorite
Home in Shanty Bay
4.9 out of 5 average rating, 70 reviews

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

KenRating, 5 stars3 weeks ago
We had a fantastic stay! The home was clean, quiet, and nestled in a beautiful, peaceful community — the view from the balcony is perfect for morning coffee or evening wine. There are walking trails just steps from the front door, and it’s a great jumping-off point for exploring Horseshoe Valley or spending the day at Vettä Spa. We didn’t use the pool or hot tub since we opted for the spa, but having access to those amenities is a great bonus for anyone staying longer. The hosts were friendly and responsive, and the space had everything we needed for a relaxing weekend getaway. Would definitely recommend to anyone looking for a peaceful escape with nature close by.
Guest favorite
Home in Innisfil
4.92 out of 5 average rating, 48 reviews

2 Bd Boardwalk Condo Patio Oasis

DavidRating, 5 stars1 week ago
Had a great time with wife and 2 daughters Would definitely get this place again from. Tristan
Guest favorite
Home in Barrie
4.93 out of 5 average rating, 94 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

DianeRating, 5 stars6 days 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.
Guest favorite
Home in Midland
4.8 out of 5 average rating, 45 reviews

Our vacation home. Fully equipped. Pool. Fire Pit.

AnneRating, 5 stars4 months ago
We were so satisfied for being the first time we booked a AIRBNB. We like the clean airy atmosphere when we walked in. Kitchen was fully equipped for our needs. ( I do a lot of cooking ). We were there for 6 weeks. Our hosts were always in contact to make sure our needs were met. We so enjoyed Midland and everyone was so friendly. We highly recommend this AIRBNB👍💗
Guest favorite
Home in Port Perry
4.93 out of 5 average rating, 220 reviews

Home away from home with a hot tub and pool

CourtneyRating, 5 stars1 week ago
lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot
Guest favorite
Home in Uxbridge
5 out of 5 average rating, 33 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

SarahRating, 5 stars2 weeks ago
This is a wonderful Airbnb in a really special place away from the hustle and bustle of everyday life. You are in a quiet location within easy access of trails where you can run or walk and if you like to ride, there are plenty of equestrian places providing this facility including part of the Airbnb itself. Youssef and his family were welcoming and on hand to provide advice as needed. That said, they were never intrusive. The accommodation is spacious and homely and you certainly do not feel like rushing out but rather enjoying the facilities. There is everything that you could need for a short or extended stay. Towels were plentiful as were shampoo and lots of extras in the bathrooms and kitchen. The heated pool is a real bonus for children or adults that like a daily swim and although shared with the family, I never felt restricted in its use and loved the fact that it was heated so was comfortable regardless of the external temperature. A wonderful stay and perfect host.
Superhost
Home in Keswick South
4.75 out of 5 average rating, 32 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

MeenuRating, 5 stars1 month ago
Myself and my friends had a pleasant staycation at Xin’s house in May. I had given a heads up that there will be a 4 months baby with us and they made sure the entire space is clean making it most comfortable especially for the baby. The host was super responsive from the time I booked and replied to my questions in a timely and respectful manner. Highly recommend to anyone looking for a spot not very far from city yet appreciate a peaceful and relaxing atmosphere.
Guest favorite
Home in Beaverton
4.84 out of 5 average rating, 45 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

DarshpreetRating, 5 stars1 week ago
We had an amazing stay at this cottage! Went with both friends and family, and it was the perfect getaway for everyone. The property is beautiful, peaceful, and super well-maintained — exactly what we needed to unwind and enjoy nature. The backyard was great for lawn games, and the indoor space was clean, cozy, and fully stocked with everything we needed. Chris and Rachael were fantastic hosts — super responsive, friendly, and made sure everything was perfect for our stay. You can really tell they care about their guests’ experience. We’re already talking about coming back! Highly recommend this spot to anyone looking for a relaxing escape. Thanks again, Chris and Rachael!

Condo rentals with a pool

Top guest favorite
Condo in Innisfil
5 out of 5 average rating, 41 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

ElenaRating, 5 stars9 months ago
We recently had the pleasure of staying at a fantastic condo in Friday Harbour, and we can’t recommend it highly enough! From the moment we arrived, we were greeted with warm hospitality and a stunning view that took our breath away. The condo itself was a perfect blend of luxury and comfort. It was impeccably clean, stylishly decorated, and equipped with all the amenities one could wish for. One of the highlights of our stay was the private balcony, where we spent many mornings sipping coffee and evenings watching the sunset over the harbor. The location of the condo is unbeatable. Just a short walk to charming local shops, restaurants, and the marina, it offered the perfect mix of relaxation and convenience. Overall, our stay at this condo in Friday Harbour was exceptional. It’s clear that the owners have put a lot of thought and care into creating a perfect retreat. If you’re looking for a memorable getaway, this place should be at the top of your list!
Guest favorite
Condo in Innisfil
4.94 out of 5 average rating, 35 reviews

Cozy south view suite overlooking the nature trail

KimberlyRating, 5 stars2 weeks ago
Loved our stay! Place was spotless and just as described, and check-in was smooth with clear instructions. Unfortunately the Nature Preserve was closed during our stay, and the pool was closed for maintenance, but Lina was accommodating otherwise. One thing to note is that the unit is right next to a stairwell exit, so if you have a sensitive dog like ours, they may be disturbed by some noises. Thanks again for the great stay!
Superhost
Condo in Shanty Bay
4.68 out of 5 average rating, 40 reviews

Lux Studio in Horseshoe Valley

LiezelRating, 5 stars6 days ago
Very accommodating and flexible, and they didn’t hesitate to approve our last-minute late check-in request.
Guest favorite
Condo in Oro
4.97 out of 5 average rating, 29 reviews

Spacious 1 bedroom condo in Carriage Hills (2248)

TaraRating, 5 stars2 weeks ago
We had a lovely time, enjoyed a golden sunset through the trees. Walkable from the Vetta Spa, if you choose, but also a quick drive.
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 favorite
Condo in Oro
4.83 out of 5 average rating, 35 reviews

Cozy Studio + Kitchenette & 1 Free Parking

TamarisRating, 5 stars3 weeks ago
Booked a spa day at Vetta for my birthday and needed a place somewhere close to stay and Tracy’s & Tiffany’s airbnb was ideal! It was so close to the spa, the complex/neighbourhood was so peaceful. The gym was less than a 2 minute walk away, everything was great! Tiffany and Tracey were so easy to communicate with and the airbnb itself had everything I needed! It didnt have a stove but we just simply brought home cooked meals there and warmed it up :) i had the most relaxing weekend and would definitely recommend coming back!
Guest favorite
Condo in Innisfil
4.89 out of 5 average rating, 19 reviews

Enjoy your stay at a cozy One bedroom apartment!

YugrajRating, 5 stars3 months ago
"Peaceful and Convenient Stay!" I had a great stay at this Airbnb! The place was very peaceful, making it perfect for relaxation. The location is incredibly convenient—just a 2-minute walk to Starbucks, FH Finefood grocery store, and plenty of restaurants. It made everything super easy, whether I needed coffee, groceries, or a nice meal. The host was also responsive and helpful. I’d definitely recommend this place and would love to stay again.
Guest favorite
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

SoniaRating, 5 stars9 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

Quick stats about vacation rentals with a pool in Orillia

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$16,719 GYD 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

    Couchiching Beach Park, Mariposa Market, and Tudhope Park

Destinations to explore

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