
Vacation rentals with a pool in Caledon
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Top-rated rentals with a pool in Caledon
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Popular amenities for Caledon rentals with a pool
House rentals with a pool

Vineyard Estate by the River with Pool!
This property is stunning! It has beautiful views of the vineyard and great walking trails. Plenty of storage and closet space, comfortable beds, the house is very spacious and perfect for a couples getaway. The local wineries looked beautiful, unfortunately we didn’t have time to visit any of them. Short distance into town with some great boutiques and art galleries.

Luxury House with a Bright Sunroom & a heated pool
A perfect spot for a large group! The pool was great and the common space was large and comfortable! Bedrooms were good size and beds were comfy! Our host was gracious and even brought a birthday cake for my husband. Would definitely stay again!

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub
This is the perfect place to stay at Niagara Falls! It’s located in a quiet neighborhood away from the busy tourist areas, but close enough to walk to all of the fun. It’s a 5 minute drive to the falls, and a 10-15 minute walk to Clifton Hill. We walked down to Clifton Hill every night for dinner/ shopping/ and entertainment, and even walked to the falls at night to see the lights. The house is beautiful, and is thoughtfully stocked with everything you could want or need. Our kids especially loved the attic playroom, full of toys, games, and books, the large basket of blocks in the living room, and the pool and hot tub out back. There are also several games and puzzles in the dining room. The two full bathrooms and one half bath were convenient, and the washer and dryer were definitely a perk as well. We would absolutely stay here again!

Luxe 5 Bed Home w/ Pool | Easy Access to GTA
Absolutely amazing house, we loved our stay there it’s great for everyone, for kids plenty of toys and books and all sort of other things. For adults there is a gym, great playground, deck, lots of bathroom and bedrooms. Overall everyone was. Wry impressed with the house and convenient location. Host was great and very accommodating.

Cheerful 3 Bedrooms Available for Renting!
My family and I love traveling and finding unique places to stay and this is definitely my favorite of them all . Ankush’s home was just breathtaking from the spacious bedrooms (especially the master bedroom with the tub) to the giant kitchen, the family oriented living room, a private office, the perfect medium size pool in the back yard that can be set to the right temperature of your choice, a yard big enough for a bbq and chill under the patio. What I love about this home, is I felt secure not just with the home but the area, everywhere on the outside, the neighborhood had cameras. We stayed from the 5-11september 2024 . We checked out 3am in the morning on our way to the airport everything was going wrong . The kids were fussy, flight delayed, it was just stressful. At 5am I picked up the phone and call Ankush to ask if the house was available for one more day,he said yes . With his prompt response we stayed till the 15th. Ankush Thanks for everything. Sure will be back!!

Luxury Hockley Estate Spa
It was a great location and hosted a large group. Very nice place in a remote area, giving us the feeling of an outdoor oasis.

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

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool
Beautiful place. The hosts were so kind and helpful. The area is safe and so close to the outlets which was a huge plus for us ladies! Hope to stay there again one day!
Condo rentals with a pool

Lovely 2-bedroom at Friday Harbour
Gorgeous condo! Wonderful People, highly recommend

Chic Studio w/ Pool | Near Lawrence West Subway
Andrews Place is perfect for a solo traveler. The property is clean, private, and offers excellent transport access to very interesting places. You can catch a direct bus from Toronto YYZ Airport with no need to change buses, and it's just less than a 10-minute walk to the property from the bus stop. It was truly great value for money.

Hidden gem in Humber bay shores Toronto w/ parking
Super convenient area for getting around the city. Very clean and super friendly host.

Friday Harbor Upscale 1Bed+Sofabed+Pool Option
We had an amazing time at Kevin’s place! It was the perfect peaceful getaway from the city. The home was clean, comfortable, and exactly what we needed to relax and unwind. Kevin was a great host—very responsive to messages and incredibly accommodating, even allowing us a late check-out which we really appreciated. He provided clear and detailed instructions for accessing the place, which made everything smooth and easy. Thank you, Kevin, for being so thoughtful and welcoming. We’d definitely love to come back again!

Luxury 1BD Condo w/ Stunning Views - Toronto
Staying at Stephanie’s was amazing. It was a great location from the airport and the local station. Close to a supermarket for food and essentials. The host was extremely helpful with a fantastic information pack provided upon arrival with everything you need to know about the apartment and the local area. It was a very clean apartment. Beautiful views and very affordable with great value for money. I would recommend staying at this accommodation to anyone visiting Toronto. I will be coming back here for sure. Thank you for being such a great host.

Luxury 1 Bedroom Suite In Heart Of Toronto
Great place, extremely close to CN Tower and Roger’s Stadium and check in was really easy with clear instructions for check in/check out

Exceptional 2+1 ground floor condo @Friday Harbour
Loved this place so much! Shai was amazing. Definitely will be coming back!

“Amazing 2 Bedrooms Condo” in Downtown Toronto”
Booking with Erkan was a pleasure and their place was fantastic. Clear instructions, easy to find and access and very well kept. The location was great and the view was wonderful. Erkan was very accommodating and responded quickly with all my questions. Overall a wonderful place to stay!
Quick stats about vacation rentals with a pool in Caledon
Total rentals
70 properties
Total number of reviews
1.9K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens