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Simcoe Vacation Rentals with Pools

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7.9 (154 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
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9.4 (35 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
7.8 (791 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
10.0 (1 Review)
Other
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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7.4 (362 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

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Why Choose Rent By Owner for your Simcoe Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Simcoe

When should you plan your Vacation Rentals with Pools stay?

Choosing the right time to vacation in this destination ensures you enjoy optimal weather and availability when seeking top-quality rentals with pools in Simcoe, Ontario, Canada, making your stay both comfortable and memorable.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy ideal weather for relaxing by your private pool in this destination. The region experiences longer days and plenty of sunshine, making it perfect for outdoor activities and leisurely swims.

Average Temperature Daytime: around 24°C to 27°C - Nighttime: around 15°C to 17°C
autumn
Early Fall (September to October)

As the weather remains mild and welcoming, early fall is a popular time to visit here and take advantage of pleasant temperatures and fewer crowds at your rental with a pool. This season offers an excellent blend of comfortable weather and serene surroundings.

Average Temperature Daytime: around 19°C to 22°C - Nighttime: around 10°C to 13°C

Off-Season Highlights

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Late Fall to Early Winter (November to December)

During these cooler months, fewer visitors come to this area, offering a more peaceful experience at your rentals with pools. While outdoor swimming may be less appealing, indoor amenities and cozy evenings become highlights of your stay.

Average Temperature Daytime: around 5°C to 10°C - Nighttime: around -2°C to 3°C
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Winter (January to February)

In the cold winter months, visiting here allows you to enjoy a quiet retreat. Many rentals with pools feature indoor options that make it easy to relax comfortably indoors while the outside air is crisp and chilly.

Average Temperature Daytime: around -3°C to 2°C - Nighttime: around -8°C to -3°C

Weekly Weather Forecast for Simcoe

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor swimming pool to relax and unwind during your stay.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Benefit from lush, landscaped gardens that enhance the outdoor ambiance.
  • Make use of outdoor barbecue grills for convenient grilling options in the region.
  • Relax by a scenic outdoor fireplace or fire pit available at many properties.
  • Explore nearby walking trails or outdoor recreational areas with easy access from your rental.
  • Utilize outdoor furniture to enjoy sunny days and picturesque surroundings in this destination.
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Family Activities

  • Simcoe County Museum Discover the region’s rich history through engaging exhibits and interactive displays that are perfect for family learning experiences.
  • Big Creek Conservation Area Enjoy outdoor adventures like hiking, birdwatching, and picnicking in this scenic natural setting suitable for all ages.
  • Local parks and splash pads: Cool off and have fun with your family at nearby parks equipped with water features and playgrounds, ideal for a relaxing day out.
  • Arts and cultural events Participate in family-friendly festivals and performances held throughout the year that celebrate local arts and traditions in the area.
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Adult Activities

  • Visit Kelso Conservation Area: Enjoy a day exploring scenic trails, outdoor activities, and relaxing by natural water features within this beautiful conservation area.
  • Explore the Niagara Escarpment: Take in breathtaking views along the rugged landscapes and discover local hiking routes perfect for nature enthusiasts.
  • Discover local vineyards and wineries: Experience wine tastings at nearby vineyards, offering a taste of regional flavors amid picturesque settings.
  • Enjoy a round of golf at area courses: Play on well-maintained golf courses that cater to both beginners and experienced players seeking a leisurely activity.

Other Places to Stay in Simcoe, ON

Hay Creek Conservation Area
Wooden Bear L Winery
Eva Brook Donly Museum & Archives
Norfolk Arts Centre
Wagon Wheel Produce & Corn Maze
War Memorial Carillon Tower

Simcoe Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead Book your rentals with pools early to secure the best options and enjoy a stress-free stay in this region.
  • Explore Local Amenities Take advantage of nearby facilities and services to enhance your experience during your visit to the area.
  • Maximize Pool Time Schedule your days to include ample relaxation by the pool at your rental, making the most of your luxurious amenities.
  • Discover Nearby Attractions Use local resources and guides to find interesting spots around here that complement your stay and create lasting memories.

Transportation Options

  • Public Transit The regional transit system offers convenient bus services within the area, making it easy to explore without a vehicle.
  • Car Rentals Numerous car rental agencies in the region provide flexible transportation options for visitors seeking independence and convenience.
  • Taxi and Rideshare Services Taxis and rideshare providers are readily available, offering quick and reliable transport throughout here and nearby destinations.
  • Bike Sharing For a more eco-friendly choice, bike-sharing programs are accessible, allowing you to enjoy scenic routes at your own pace.

Local Customs Options

  • First Nations Traditions: The area respects local Indigenous customs, which often include storytelling and ceremonies that honor the land’s heritage.
  • Ontario Harvest Festivals: Celebrate local agriculture by participating in seasonal festivals that showcase regional produce and traditional foods.
  • Community Events and Parades: Local communities frequently host parades and gatherings that highlight regional pride and cultural history.
  • Respect for Nature and Conservation: There is a strong emphasis on environmental preservation, encouraging visitors to enjoy the natural surroundings responsibly.

Frequently Asked Questions About Simcoe Rentals with Pools

1. What are the top Rentals With Pools in Simcoe?

2. How many Rentals With Pools are available in Simcoe?

Currently, the total number of properties listed by RBO in 2026 is over 4 in the Simcoe area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Simcoe. 

3. What is the cancellation policy for rentals with pools in Simcoe, Ontario?

The cancellation policy varies depending on the individual property listing. You will need to review the specific rental details or contact the property owner directly to understand the terms related to cancellations and refunds.

4. Are there any additional fees associated with booking a property with a pool in this area?

Additional fees such as cleaning, security deposits, or service charges may apply. Details about any extra costs are typically outlined in the property listing, so it’s recommended to read the full description or reach out to the host for clarification.

5. What amenities are usually included in rentals with pools in Simcoe?

Most properties come equipped with standard amenities like Wi-Fi, kitchen facilities, and air conditioning. Specific features related to the pool, such as safety measures or outdoor furniture, are listed in each property’s details-checking these will help you find the best fit for your stay.

6. Can I book a rental with a pool in Simcoe for a short-term stay?

Yes, many listings cater to short-term visitors and provide flexible booking options. Availability depends on the specific property, so reviewing the listing’s minimum stay requirements and contacting the owner if necessary can ensure your plans align.

7. What should I do if I encounter issues during my stay at a rental with a pool?

If you experience any problems, contact the property owner or local management team listed in your reservation details. They are responsible for assisting you promptly to ensure your stay remains comfortable and enjoyable.

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