176+ Private Villas and Holiday Rentals in Winter Park |
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Winter Park Holiday Rentals

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

Discover more than 176 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 791.83 ft², with nightly prices averaging GB £164.

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 98
Holiday Apartments 43
Villas 5
Cottages 2

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, FL

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

December - February
High 38°F       Low 2°F
March - May
High 55°F       Low 18°F
June - August
High 75°F       Low 34°F
September - November
High 67°F       Low 19°F

Top Attractions Around Winter Park, FL

Casai offers a large selection of top attractions around Winter Park . Research things to do on your vacation before you visit Winter Park.


Full Sail University
Rollins College
Winter Park Village
Kraft Azalea Gardens
Casa Feliz Historic Home Museum
Mead Garden
Lee Road Shopping Center
Morse Museum of American Art
Lake Virginia
Albin Polasek Museum and Sculpture Gardens
Crealde School of Art
All Fired Up
Winter Park Playhouse
Alfond Swimming Pool
Winter Park Country Club
Winter Park Corner Shopping Center
The Center of Winter Park Shopping Center
Virginia S. Nelson Rose Garden
Winter Pines Golf Club
Winter Park History Museum

Other Places to Stay in Winter Park, FL


Mead Garden 622 Properties
Hollie Anna Shopping Center 509 Properties
Alfond Swimming Pool 450 Properties
Lake Rose 449 Properties
Lake Virginia 448 Properties
Winter Park Playhouse 446 Properties
Lee Road Shopping Center 421 Properties
All Fired Up 410 Properties
Cahall Sandspur Field 403 Properties
Hannibal Square Heritage Center 403 Properties
Virginia S. Nelson Rose Garden 398 Properties
Goldenrod 127 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 176 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 (6) 
Neighborhood Property Count
Northeast Orlando Vacation Rentals in Orlando, Florida 661
College Park Vacation Rentals in Orlando, Florida 39
Goldenrod Vacation Rentals in Orlando, Florida 127
North Orange Vacation Rentals in Orlando, Florida 796
Baldwin Park Vacation Rentals in Orlando, Florida 151
Orwin Manor Vacation Rentals in Orlando, Florida 775

People Also Ask

There are 176 Winter Park, FL Holiday Rentals

Recently Booked Holiday Rentals in Winter Park