307+ Private Villas and Holiday Rentals in Winter Garden |
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Winter Garden Holiday Rentals

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

Discover more than 307 vacation rentals available in Winter Garden. 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 Garden.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Garden, 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 Garden. On average, places to stay near Winter Garden offer 660.55 ft², with nightly prices averaging CA $340.

With Casai, finding and comparing holiday rentals in Winter Garden 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 Garden

Type Count
Vacation Homes 78
Holiday Apartments 51
Villas 50
Cottages 6

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

★ 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 Garden.

Weather in Winter Garden, FL

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

December - February
High 79°F       Low 53°F
March - May
High 91°F       Low 57°F
June - August
High 92°F       Low 71°F
September - November
High 90°F       Low 60°F

Top Attractions Around Winter Garden, FL

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


Orange Lake Golf
Orange County National Golf Club
Disney's Magnolia Golf Course
Resurrection Catholic Church
Disney's Palm Golf Course
West Orange Trail
Winter Garden Art Association
Disney's Oak Trail Golf Course
Winter Garden Heritage Museum
Surfari Water Park
West Orange Country Club
Carter Family Bowl
Oakland Nature Preserve
Garden Theatre
Central Florida Railroad Museum
AdventHealth Winter Garden
Walt Disney World® area
Walt Disney World® Resort
Lake Louisa State Park
Lake Butler

Other Places to Stay in Winter Garden, FL


Orange Lake Golf 18,016 Properties
Vista del Lago 13,817 Properties
Surfari Water Park 10,625 Properties
Orange County National Golf Club 2,077 Properties
West Orange Country Club 216 Properties
Disney's Palm Golf Course 180 Properties
Disney's Magnolia Golf Course 143 Properties
Disney's Oak Trail Golf Course 143 Properties
Orange Lake 120 Properties
AdventHealth Winter Garden 99 Properties
Resurrection Catholic Church 97 Properties
Oakland 49 Properties

Frequently Asked Questions About Winter Garden?

What are the top holiday rentals in Winter Garden?

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

How many holiday rentals have private pools in Winter Garden?

Discover a selection of holiday rentals with private pools near Winter Garden 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 Garden are best for families?

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

How many Casai.ca holiday rentals are available in Winter Garden?

As of 2025, Casai boasts over 307 properties listed in the Winter Garden area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Garden.

Nearby Neighborhood (6) 
Neighborhood Property Count
West Kissimmee Vacation Rentals in Orlando, Florida 17191
Bay Lake Vacation Rentals in Orlando, Florida 1002
Orange Lake Vacation Rentals in Orlando, Florida 120
Vista del Lago Vacation Rentals in Orlando, Florida 13817
Oakland Vacation Rentals in Orlando, Florida 49
Killarney Vacation Rentals in Orlando, Florida 26

People Also Ask

There are 307 Winter Garden, FL Holiday Rentals

Recently Booked Holiday Rentals in Winter Garden