466+ Private Villas and Holiday Rentals in Winter Park |
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  2. California
  3. Big Bear Lake
  4. Winter Park

Winter Park Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winter Park

Discover more than 466 vacation rentals available in Winter Park. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Park.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Park, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Park. On average, places to stay near Winter Park offer 1729.7 ft², with nightly prices averaging GB £444.

With Casai, finding and comparing holiday rentals in Winter Park is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winter Park

Type Count
Vacation Homes 210
Holiday Apartments 19

Use these Quick Filters to Find a Holiday Rental in Winter Park

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winter Park.

Weather in Winter Park, CA

View the weather forecast for Winter Park before booking your Winter Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay in Winter Park, CA


Summit Estates 304 Properties

Frequently Asked Questions About Winter Park?

What are the top holiday rentals in Winter Park?

With numerous options available in Winter Park, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Park:

How many holiday rentals have private pools in Winter Park?

Discover a selection of holiday rentals with private pools near Winter Park with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winter Park are best for families?

If you're searching for a family-friendly holiday home in Winter Park, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Park:

How many Casai.uk holiday rentals are available in Winter Park?

As of 2025, Casai boasts over 466 properties listed in the Winter Park area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Park.

Nearby Neighborhood (2) 
Neighborhood Property Count
Summit Estates Vacation Rentals in Big Bear Lake, California 304
Evergreen Estates Vacation Rentals in Big Bear Lake, California 283

People Also Ask

There are 466 Winter Park, CA Holiday Rentals

Recently Booked Holiday Rentals in Winter Park