44+ Private Villas and Holiday Rentals in Winter Springs |
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Winter Springs Holiday Rentals

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

Discover more than 44 vacation rentals available in Winter Springs. 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 Springs.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Springs, 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 Springs. On average, places to stay near Winter Springs offer 825.46 ft², with nightly prices averaging CA $315.

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

Type Count
Vacation Homes 37
Holiday Apartments 5
Cottages 1

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

★ 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 Springs.

Weather in Winter Springs, FL

View the weather forecast for Winter Springs before booking your Winter Springs 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

Top Attractions Around Winter Springs, FL

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


Central Winds Park
Tuscawilla Golf Course
Trotwood Park
Universal Orlando ResortTM
Universal Studios FloridaTM
Orange County Convention Center
Florida Mall
Orlando International Premium Outlets
Amway Center
Camping World Stadium
Holy Land Experience
The Wizarding World of Harry PotterTM
University of Central Florida
The Wheel at ICON ParkTM
Universals Islands of AdventureTM
Mall at Millenia
Pointe Orlando
Orlando Science Center
Universal CityWalk
CoCo Key Water Resort

Other Places to Stay in Winter Springs, FL


Trotwood Park 32 Properties
Central Winds Park 29 Properties
Tuscawilla Golf Course 26 Properties

Frequently Asked Questions About Winter Springs?

What are the top holiday rentals in Winter Springs?

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

Which holiday homes in Winter Springs are best for families?

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

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

As of 2026, Casai boasts over 44 properties listed in the Winter Springs area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Springs.


People Also Ask

There are 44 Winter Springs, FL Holiday Rentals

Recently Booked Holiday Rentals in Winter Springs