Vacation rentals with a pool in Caledon

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Caledon rentals with a pool

House rentals with a pool

Guest favorite
Home in Niagara-on-the-Lake
4.87 out of 5 average rating, 45 reviews

Vineyard Estate by the River with Pool!

SarahRating, 5 stars1 month ago
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.
Guest favorite
Home in Mississauga
4.96 out of 5 average rating, 24 reviews

Luxury House with a Bright Sunroom & a heated pool

MargieRating, 5 stars6 days ago
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!
Guest favorite
Home in Niagara Falls
4.91 out of 5 average rating, 106 reviews

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub

BrittanyRating, 5 stars1 week ago
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!
Top guest favorite
Home in Mississauga
5 out of 5 average rating, 11 reviews

Luxe 5 Bed Home w/ Pool | Easy Access to GTA

DmitriyRating, 5 stars3 weeks ago
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.
Superhost
Home in Brampton
4.79 out of 5 average rating, 14 reviews

Cheerful 3 Bedrooms Available for Renting!

GaneshRating, 5 stars9 months ago
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!!
Superhost
Home in Mono
4.55 out of 5 average rating, 11 reviews

Luxury Hockley Estate Spa

ScottRating, 5 stars2 weeks ago
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.
Guest favorite
Home in East Gwillimbury
5 out of 5 average rating, 5 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

AbdulmalikRating, 5 stars1 month ago
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.
Guest favorite
Home in Niagara-on-the-Lake
4.79 out of 5 average rating, 230 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

ChandraRating, 5 stars3 weeks ago
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

Superhost
Condo in Innisfil
4.83 out of 5 average rating, 481 reviews

Lovely 2-bedroom at Friday Harbour

JoshuaRating, 5 stars3 days ago
Gorgeous condo! Wonderful People, highly recommend
Superhost
Condo in North York
4.8 out of 5 average rating, 106 reviews

Chic Studio w/ Pool | Near Lawrence West Subway

KayodeRating, 5 stars3 days ago
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.
Guest favorite
Condo in Toronto
4.93 out of 5 average rating, 152 reviews

Hidden gem in Humber bay shores Toronto w/ parking

RebeccaRating, 5 stars1 month ago
Super convenient area for getting around the city. Very clean and super friendly host.
Guest favorite
Condo in Innisfil
4.89 out of 5 average rating, 143 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Tanuja KajalRating, 5 stars3 weeks ago
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!
Superhost
Condo in Mimico-Queensway
5 out of 5 average rating, 5 reviews

Luxury 1BD Condo w/ Stunning Views - Toronto

WilliamRating, 5 stars4 days ago
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.
Guest favorite
Condo in Downtown Toronto
4.92 out of 5 average rating, 277 reviews

Luxury 1 Bedroom Suite In Heart Of Toronto

NicoRating, 5 stars1 week ago
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
Guest favorite
Condo in Innisfil
4.93 out of 5 average rating, 115 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

VictoriaRating, 5 stars2 weeks ago
Loved this place so much! Shai was amazing. Definitely will be coming back!
Guest favorite
Condo in Downtown Toronto
4.98 out of 5 average rating, 101 reviews

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

JasonRating, 5 stars2 weeks ago
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

Destinations to explore