$20 Car Rental Winter Park, FL

Reasons to book a car rental in and around Winter Park

Renting a car in Winter Park provides an excellent opportunity to explore this charming city and its surroundings at your own pace. For theme park enthusiasts and outdoor lovers, having a vehicle allows for easy travel to nearby attractions, making it convenient to manage luggage and plan flexible itineraries. Within just 3 miles, you can visit the Orlando Science Center, ideal for family experiences, or head 5 miles to the Dr. Phillips Center for the Performing Arts for a dose of culture. Additionally, the vibrant atmosphere of Orange Avenue, also 5 miles away, offers a great city experience to enjoy.

A rental car also opens the door to popular nearby destinations. Explore the metropolis of Orlando, which is home to the renowned Walt Disney World® Resort, or venture to Casselberry, located 5 miles away, featuring scenic parks and attractions like Wekiwa Springs State Park. Whether you are traveling with family or seeking entertainment, having a rental car in Winter Park makes your journey comfortable and hassle-free, ensuring you can visit all the sights that interest you without the constraints of public transportation.

Most popular car rentals in Winter Park

• Midsize SUV: This option comfortably accommodates 5 travelers and offers space for up to 3 large suitcases. Midsize SUVs are particularly well-suited for families, couples, or small groups looking to explore Winter Park and its surroundings. With a higher driving position and versatile storage, this type of vehicle ensures a pleasant travel experience, making it ideal for those planning to enjoy outdoor activities or visit nearby attractions.
• Standard SUV: Also designed for 5 travelers, the standard SUV provides room for up to 2 medium suitcases. This car type is perfect for couples, families, or groups who want a balance of comfort and utility. The standard SUV is a popular choice for those wanting to navigate the city while having enough cargo space for essentials, making it an excellent option for a mix of city-related experiences and outdoor adventures in and around Winter Park.
• Fullsize: With the capacity to fit 5 travelers and up to 3 large suitcases or 5 medium suitcases, the fullsize car is ideal for families and groups who need extra space. This vehicle type is perfect for those planning longer trips or carrying more luggage, offering the flexibility to manage travel plans and enjoy the freedom of exploring Winter Park at your own pace. The fullsize car ensures comfort and convenience during your journey.

Top rated car suppliers in Winter Park

• Budget: Budget has established itself as a reliable choice with 1 rental location in Winter Park. Travelers frequently opt for their Midsize SUV and Standard SUV models, which provide ample space for luggage and comfort for exploring the area. Known for competitive pricing, Budget enables guests to manage their travel plans with ease and flexibility.
• Hertz: With 2 convenient rental locations in Winter Park, Hertz is a popular option among travelers. Their Midsize SUV and Fullsize vehicles are highly favored, offering both comfort and capacity for families or groups. Hertz is recognized for its efficient service, making it a great choice for those looking to get on the road quickly and explore the local attractions without delay.
• Enterprise: Enterprise operates 1 rental location in Winter Park and is well-regarded for its customer-focused service. The Midsize SUV and Fullsize SUV options are popular among renters, providing a good balance of space and comfort. Enterprise is often praised for its helpful staff and smooth rental process, ensuring that you can embark on your adventures with minimal hassle.

Where to go in Winter Park

• Winter Park: Known for its charming streets and beautiful parks, Winter Park offers a delightful experience for visitors. Explore the scenic Rollins College or enjoy the local arts scene. The area is ideal for a family vacation, especially during the peak months of March, July, and December when visitor numbers are higher.
• Casselberry: Located 5 miles away from Winter Park, Casselberry is perfect for outdoor enthusiasts and families. Key attractions include Wekiwa Springs State Park for adventure and Red Bug Lake Park for urban outdoor experiences. The best times to visit are from March to April and September, when visitor numbers peak.
• Baldwin Park: This neighborhood around Winter Park is great for those seeking city and outdoor experiences. Visit Full Sail University or the Orlando Science Center for cultural insights. Peak visitor times are in March to April and July, making it a vibrant time to explore local shops and eateries.

10 tips to save on your Winter Park car hire

1. Use filters to find the right car: Refine your search by selecting vehicle types and specific features. Whether you're looking for an SUV for added space, a convertible for summer fun, or an economy car for budget-friendly travel, utilize the filters on Expedia to discover the best fit for your journey.
2. Book in advance to help lower costs: Rental prices can vary based on demand, so it's wise to secure your car well ahead of your trip. Booking early often leads to lower rates and improved availability, particularly during peak seasons.
3. Consider a smaller car for savings: Smaller vehicles typically come with lower rental costs and are easier to park in crowded areas. Mid-size options strike a good balance between price, comfort, and fuel efficiency.
4. Age guidelines: Drivers younger than 30 may encounter higher deposits or daily fees, and certain vehicle types—such as SUVs or luxury models—might not be accessible. This could also apply to renters over 70 years old. Always verify the age requirements before making a reservation.
5. Check fuel policies: Some rental agreements stipulate a full-to-full fuel policy, meaning you must return the car with a full tank to avoid additional charges. This is often the most advantageous option. Other policies may include full-to-empty or prepaid fueling options, which can be acceptable as well. Just ensure you return the car with an empty tank in that case.
6. Save on city and airport pickups: Picking up your rental car at airports often incurs a surcharge, but the convenience it offers may justify the cost.
7. Know your payment options: Most car rental companies exclusively accept credit cards for payments.
8. Understand your insurance coverage: Car rental insurance can help you avoid unexpected expenses and provide peace of mind if something unforeseen occurs during your trip. It's easy to add car rental insurance when booking through Expedia.
9. Consider unlimited mileage: If you plan on taking long road trips, seek out rentals that offer unlimited mileage to prevent incurring extra charges.
10. Bring your driver's license and ID: A valid driver's license is necessary to rent a car.

Best time to rent a car in and around Winter Park

The best time to rent a car in and around Winter Park is September, when both prices and demand are at their lowest. April and May also offer slightly low prices and demand, making them good options for budget-conscious travelers. However, July is typically the most expensive month, with high demand and prices. June and August see average demand and pricing, while December experiences the highest demand and elevated costs for rentals.

Calendar Month	Temperature	Precipitation	Cloudiness	Demand	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
February	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Average	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
June	81.0°F (27.2°C)	Light Rain	Mostly Sunny	Average	Average
July	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	82.6°F (28.1°C)	Moderate Rain	Mostly Sunny	Average	Average
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Average	Average
November	68.2°F (20.1°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
December	64.0°F (17.8°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Slightly High

Finding the cheapest car rentals in Winter Park

Using our Search Wizard

If the deals that are available on our page do not suit your needs, then enter Winter Park into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Winter Park and provide you with a list of the cheapest options, with no added fees.

Renting a car in Winter Park

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Winter Park. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia.

Expected prices in Winter Park

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $20.

Flexibility & Cancellation

Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the Trips portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled.

We all love being rewarded

One Key members save 10% or more on select hotels, cars, activities and vacation rentals. Not only that, earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands: Expedia, Hotels.com and VRBO. Learn more and join today.

Car classes available from Expedia in 2026

The classes of vehicles available will change depending on your chosen location.

• Compact car rentals    
• Convertible car rentals    
• Economy car rentals    
• Fullsize car rentals    
• Luxury car rentals
• Midsize car rentals    
• Mini car rentals    
• Minivan rentals    
• Pickup car rentals    
• Premium car rentals
• Sportscar rentals    
• Standard car rentals    
• SUV rentals    
• Van rentals