
Vacation rentals with a pool in Simcoe County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Simcoe County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Simcoe County rentals with a pool
House rentals with a pool

Spacious Chalet close to Ski resort. Pet friendly!
Our stay at Tuan’s place was as expected! It was great having so many things to do all in one place. The hot tub and pool table were a huge hit for our group! Tuan and his family were very responsive, which made our check in and check out very easy. The only constructive feedback is the basement could be cleaned more thoroughly, and information on the shuttle bus would have been helpful. We ended up walking to the village for dinner on Saturday night, which was about a 20 minute walk. Overall, Happy Home was the perfect place to stay for our friend’s getaway weekend!

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

Spacious 4BR Snowbridge Home with Shuttle Access
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.

Cozy Pool house in Newmarket
Great stay. Brought the family there for a weekend of pool fun. My kids are 3 and 16 months. Minoo is a great host and very responsive. The home is meticulous but not particularly kid friendly - she was upfront and described this to me in advance. If you have a little one that likes to explore on their own - you need to keep an eye on them, lots of little decorations at arms reach for the kids. Spiral staircase can be difficult to use with kids in your arms as well. Pool was beautiful and warm however is not a walk in and the shallow end is a third of the pool. We spent most of our time in the private backyard or out for walks. Local parks and amenities close by. We had a great time and would absolutely stay at Minoos place again when visiting Newmarket. Thanks for the hospitality Minoo !!

Serene mountainside home View/Shuttle Bus/Pool
We had a wonderful stay - Brendan's place was clean, organized and in a great area (close to village). Brendan was responsive and helpful and I would recommend this place to relax and enjoy Collingwood.

Large 4 br and 3 full bathroom/Sauna by Village
Our stay was awesome, the house is amazing, very close to the slopes and the amenities were great!

Custom home that feels like the Spa
Great place to stay and very the host was awesome. Exactly as described.

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.
Condo rentals with a pool

Large, luxury, upper floor condo, steps to Village
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.

The Fairway Chalet
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.

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft
We enjoyed our stay. Walking distance to the ski lift, lots of parking space, good price for the apartment. Would definitely stay again!

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).

2 Bedroom, 2 Level Condo on Blue Mountain!
The property was as advertised. It was clean and functional. We asked for help a couple of times and were given prompt and immediate answers. Highly recommended!

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.

Friday Harbour Luxury Condo, Sleeps 4
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
Destinations to explore
- Rentals with breakfast Simcoe County
- Rentals with beach access Simcoe County
- Boutique hotel rentals Simcoe County
- Rentals with a washer and dryer Simcoe County
- Bungalow rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Villa rentals Simcoe County
- Bed and breakfasts Simcoe County
- Chalet rentals Simcoe County
- Waterfront rentals Simcoe County
- House rentals Simcoe County
- Townhouse rentals Simcoe County
- Pet-friendly rentals Simcoe County
- Cabin rentals Simcoe County
- Rentals with a sauna Simcoe County
- Beachfront rentals Simcoe County
- Rentals with a kayak Simcoe County
- Tiny house rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Cottage rentals Simcoe County
- Guesthouse rentals Simcoe County
- Apartment rentals Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Hotel rentals Simcoe County
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Private suite rentals Simcoe County
- Luxury rentals Simcoe County
- Family-friendly rentals Simcoe County
- Fitness-friendly rentals Simcoe County
- Farmstay rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Loft rentals Simcoe County
- Rentals with a patio Simcoe County
- Kid-friendly rentals Simcoe County
- Rentals with a firepit Simcoe County
- Rentals with an EV charger Simcoe County
- Rentals with pools Ontario
- Rentals with pools Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- TPC Toronto at Osprey Valley
- Georgian Bay Islands National Park
- Hockley Valley Resort - Golf, Spa and Ski
- Beaver Valley Ski Club
- Muskoka Lakes Golf and Country Club
- Lakeridge Ski Resort
- Lake Joseph Golf Club
- Devil's Glen Country Club
- Angus Glen Golf Club
- Summit Golf & Country Club
- South Muskoka Curling and Golf Club
- Caledon Country Club
- The Georgian Peaks Club
- Alpine Ski Club
- National Pines Golf Club
- LEGOLAND Discovery Centre Toronto
- Bushwood Golf Club
- Granite Golf Club
- Things to do Simcoe County
- Things to do Ontario
- Tours Ontario
- Wellness Ontario
- Sightseeing Ontario
- Art and culture Ontario
- Sports activities Ontario
- Entertainment Ontario
- Nature and outdoors Ontario
- Food and drink Ontario
- Things to do Canada
- Sightseeing Canada
- Nature and outdoors Canada
- Sports activities Canada
- Art and culture Canada
- Entertainment Canada
- Wellness Canada
- Food and drink Canada
- Tours Canada