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Caledon villas
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252 Villa rentals in Caledon

Browse Holiday Homes with a Pool in Caledon

Go for a private swim or lounge poolside in total seclusion whenever you please at houses with a pool in Caledon.

Fabulous Family Retreat, 1hr From To, Sleeps 8 - Caledon
10 1 review

Fabulous Family Retreat, 1hr From To, Sleeps 8

bungalow, Orangeville
This detached house is situated in Ontario's Headwaters region, just 10 kilometres from Hockley Valley Ski Resort and a short walk to Island Lake Conservation.
This family-friendly property offers accommodation for 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, hot tub, garden, and a home gym, with direct access to outdoor activities such as snowshoeing and trail walks.
House With A Pool In Caledon - Caledon
No reviews

House With A Pool In Caledon

house, Caledon
This holiday home is located in Caledon, just a short drive from Starbucks and Hockley Valley, offering easy access to local amenities and attractions. The property sits on a half-acre plot, providing privacy and ample space for gatherings.
The house has four bedrooms and one bathroom, sleeping up to ten guests. Enjoy the above-ground pool, outdoor fire pit, and ample parking, as well as a fireplace, pool table, and spacious kitchen.
Mono Springs - Dream Country Escape W Pool/hot Tub - Caledon
9.8 51 reviews

Mono Springs - Dream Country Escape W Pool/hot Tub

house, Orangeville
This four-bedroom apartment is located in Mono, a rural area just 15 kilometres from Orangeville town centre, offering a peaceful escape from the hustle and bustle. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features a spacious and well-equipped kitchen, perfect for self-catering, and can comfortably accommodate up to eight guests. Enjoy a range of amenities including a private hot tub, a heated swimming pool (seasonal), a large bonfire pit, and 10 acres of land with trails for exploring the surrounding countryside.
186 M² House ∙ 3 Bedrooms ∙ 6 Guests - Caledon
No reviews

186 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Orangeville
This three-bedroom townhouse is located centrally in Orangeville, Ontario, providing convenient access to the town's downtown area, local shops, restaurants, parks, and nearby attractions.
This spacious accommodation spans 185 square meters and accommodates up to six guests, featuring a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, and a terrace, with parking available.

Browse Downtown Holiday Homes in Caledon

Live like a local and walk to the best historic sights and dining spots from centrally located houses in Caledon.

Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings - Caledon
10 1 review

Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings

cottage, Caledon
Vintage Cottage Retreat, a 4-bedroom property sleeping 14, is situated in Caledon, Ontario, approximately 72km from Yorkdale Shopping Centre and conveniently located near Forks of the Credit Provincial Park and the Bruce Trail.
This 3,700 sq ft holiday home boasts a full kitchen with microwave and dishwasher, 4 bathrooms, a solarium, terrace, garden, parking, air conditioning, and a wood-burning fireplace; it also offers 10 acres of land ideal for camping, stargazing, and small events.
Caledon East Retreat - Caledon
10 30 reviews

Caledon East Retreat

house, Caledon East
The Caledon Retreat is located in Caledon East, just a short drive from the charming downtown area and within easy reach of scenic hiking and biking trails. The property has received excellent ratings for location, cleanliness and user experience.
This seven-bedroom, five-bathroom home can comfortably accommodate up to 12 guests. The retreat offers a range of amenities, including a swimming pool, Jacuzzi, sauna, fitness centre, and a spacious garden, providing plenty of opportunities for relaxation and recreation.
Cozy Tiny Home, Immersed In The Forest, Overlooking The Pond! - Caledon
10 5 reviews

Cozy Tiny Home, Immersed In The Forest, Overlooking The Pond!

cabin, Caledon East
This Caledon East cottage is situated 3 km from the Albion Hills Conservation Area and 4.2 km from Plant Paradise Country Gardens, with Legacy Pines Golf Club and Caledon Equestrian Park within a 10 km radius.
The one-bedroom, one-bathroom lodge sleeps two guests and offers heating, a private bedroom, and is ideally located for exploring the natural beauty and attractions of Caledon East.
Caledon Country Charm - Caledon
9.9 22 reviews

Caledon Country Charm

bungalow, Caledon East
This detached country house, a bungalow, is located in the Caledon East district on nearly one acre of land, offering peaceful family accommodation with convenient proximity to local amenities including grocery stores, LCBO, and a bakery, as well as nearby walking trails.
This family-friendly property accommodates up to eight guests across four bedrooms and two bathrooms, featuring a main floor layout with upgraded appliances, modern decor, air conditioning, a dishwasher, a garden, parking, and a back patio with a BBQ, ideal for enjoying expansive country views.

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View Premier Family Houses in Caledon

Keep the whole group together with multiple bedrooms, a full kitchen, and games at family houses in Caledon.

Luxury 5 Star Stay In Brampton Ideal For Groups! - Caledon
No reviews

Luxury 5 Star Stay In Brampton Ideal For Groups!

house, Caledon East
This spacious holiday home in Caledon East is situated 19 kilometres from Toronto Pearson International Airport, 16 kilometres from the Mississauga Convention Centre, and 32 kilometres from Vaughan Mills Shopping Centre.
This family-friendly property offers 279 square metres of living space with 1 bedroom, 3 bathrooms, and accommodation for up to 15 guests, featuring a fully equipped kitchen, air conditioning, free WiFi, and a garden with a terrace.
Globalstay. Modern 3 Bedroom House In Brampton - Caledon
10 1 review

Globalstay. Modern 3 Bedroom House In Brampton

house, Caledon East
This family-friendly detached house is located in Brampton, a district within the greater Caledon region, offering convenient access to local amenities.
This 177 square meter property features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, complimentary Wi-Fi, and on-site parking, with select rooms offering a balcony or terrace.
Guest House By Canterra Stays · Not A Basement - Caledon
10 11 reviews

Guest House By Canterra Stays · Not A Basement

house, Toronto
This private, above-ground coach house in Toronto's Vales of Castlemore North offers convenient access to the city and airport.
This modern suite accommodates up to three guests with one bedroom, a full kitchen featuring a fridge, freezer, and microwave, air conditioning, internet, parking, and an EV-friendly Tesla charger available for an additional fee.
Luxury - Sleeps 10 - Smart Home - Ps5 - 85 Oled - Caledon
No reviews

Luxury - Sleeps 10 - Smart Home - Ps5 - 85 Oled

house, Caledon East
This four-bedroom, four-bathroom luxury dwelling in Caledon East is situated 20.9 kilometres from Toronto Pearson International Airport, 15.9 kilometres from the Mississauga Convention Centre, and 33.8 kilometres from Canada's Wonderland.
This spacious property, covering 242 square metres, offers accommodation for up to 10 guests and includes a sauna, spa bath, and smart home technology.

Best Caledon villas and holiday homes with parking

Private Hockley Valley Farmhouse - Caledon
9.7 30 reviews

Private Hockley Valley Farmhouse

gîte, Orangeville
This three-bedroom farmhouse is located in Hockley Valley, just a short drive from Orangeville, offering easy access to the Bruce Trail, the Hockley Valley Conservation Area, and a variety of local attractions. The property enjoys excellent user, location, and cleanliness ratings, making it a top choice for travellers.
The farmhouse comfortably accommodates up to seven guests and features a modern kitchen, a wood-burning fireplace, and super-fast Wi-Fi. Guests can enjoy a secluded country setting, access to nature, nearby attractions, and a range of adventurous activities, ensuring a memorable stay.
The Loft - Caledon
9.8 33 reviews

The Loft

farm, Adjala-Tosorontio
This farm stay is situated in Adjala-Tosorontio, just 40 kilometres from Woodbine Race Track and 45 kilometres from Pearson International Airport, offering a peaceful rural escape close to major attractions. It has consistently received excellent reviews for its location, cleanliness, and overall experience.
The property comprises a three-bedroom house with one bathroom, comfortably accommodating up to eight guests. Enjoy the unique atmosphere of a working horse farm with over 300 acres of hiking trails nearby, a garden, a BBQ area, and the option of booking a tour of the facilities.
Cabin Stay And Play! 10 Mins To Canadian Open! - Caledon
9.8 535 reviews

Cabin Stay And Play! 10 Mins To Canadian Open!

cabin, Erin
This Erin, Ontario lodge is located 2km from the town centre and 0.35km from Caledon Golf Course, offering seclusion yet easy access to local amenities.
Sleeping four guests, this self-catering retreat boasts two bedrooms, one bathroom, a jacuzzi, and on-site amenities including a BBQ, patio, pool table, and Golden Tee arcade game, alongside access to acres of walking trails.
Resort Style Entire Guesthouse (2 Rooms, Kitchen) - Caledon
9.3 265 reviews

Resort Style Entire Guesthouse (2 Rooms, Kitchen)

house, Adjala-Tosorontio
This private suite is situated on conservation land just minutes from the Equestrian Park, Bruce Trail, Hockley Valley Resort, and Woodington Lake Golf, offering a peaceful retreat in the heart of Adjala-Tosorontio. The accommodation has consistently received excellent ratings for its location, cleanliness, and overall experience.
The self-contained suite features a bedroom, living room, and private bathroom, providing ample space for a comfortable stay. Guests can enjoy a fully equipped kitchen, access to a private outdoor dining area, fire pit, charcoal grill, and a spacious garden, as well as the opportunity to relax in a Jacuzzi.

Best Caledon villas and holiday homes with a garden

Character-filled Farm Guest House On 8 Acres - Caledon
9.9 81 reviews

Character-filled Farm Guest House On 8 Acres

farm, Adjala-Tosorontio
Royal Luxury Central Home With Gazebo By Toronto - Caledon
No reviews

Royal Luxury Central Home With Gazebo By Toronto

house, Toronto
A Modern 3 Bedroom Home With Free Parking & Wifi - Caledon
9.7 139 reviews

A Modern 3 Bedroom Home With Free Parking & Wifi

house, Orangeville
Executive 5br-4bath Detached Bramp/miss Border - Caledon
9.9 14 reviews

Executive 5br-4bath Detached Bramp/miss Border

house, Toronto

View Luxury Holiday Homes in Caledon

Live like royalty in a massive, high-end private estate featuring elite architecture and finishes at luxury houses in Caledon.

Lakeside Private Suite (Queen Bed Room) - Caledon
8.0 3 reviews

Lakeside Private Suite (Queen Bed Room)

house, Adjala-Tosorontio
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