Windward Side Cheap Car Rentals & Car Hire Deals

Compare rent a car rates in Windward Side from popular car rental companies

Featured car rental suppliers

Compare from agencies

car supplier logos

Compare car suppliers to unlock big savings, and package your flight, hotel, and car to save even more.

Members save 10% more on select hotels, cars and activities. Sign up.Opens in a new window

Enjoy maximum flexibility with penalty-free cancellation on most car rentals.

Explore Windward Side with Cheap Car Rentals and Car Hire Deals

* Price found within the past 60 days. Click for updated prices.

Don't see what you're looking for?

See all car hire in Windward Side
View all cars
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

How much is a rental car per day in Windward Side?
Get bang for your buck in Windward Side, with car rental prices within the past seven days starting from as low as a day.
What happens if I need to cancel my Windward Side car reservation?
There are always times when plans change. That’s why we offer a full refund on most prepaid homes if you notify us six hours in advance of the collection time. Be sure to double-check your cancellation policy — there are some cases where it’s not an option. Found nothing there? Our Customer Service Portal is always here to help.
What types of cars can I rent in Windward Side?
Bustling city streets and cramped parking spots are no issue for an economy car — the most popular home type in Windward Side. Get behind the wheel of one of these and get around traffic effortlessly. Affordable, reliable and good on gas, these small rides pack a punch. But Windward Side can be explored in almost any type of home you like. Compacts, premiums and SUVs are some other options to choose from.
Why should I rent a Windward Side car with Expedia?
Expedia is the perfect place to book your ride. With suppliers in Windward Side to select from, we’re all about finding you terrific deals. Save big with our member prices and exclusive offers, and earn rewards with every booking. Save more when you combine your bookings into a Windward Side holiday package. Car rentals, hotels, flights, activities — Expedia has everything you need in one place.
How do I find the best car rental deals in Windward Side with Expedia?
Browse our fantastic range of rental cars, check out customer recommendations and compare prices from leading brands. In just a few clicks, Expedia will help you nab the best deal on your wheels. Got a flight or hotel booking? Add on your Windward Side car rental to save even more money.
What do you need to rent a car in Windward Side?
You’ll generally require a current driver’s license and credit card in your name when picking up your car. You may also need your own proof of coverage if you’d like to opt out of the company’s insurance policy. Requirements are likely to differ between suppliers, so it’s wise to check while booking.
What is the cheapest car rental in Windward Side?
The two lowest daily rates recorded in Windward Side within the past seven days were and . Now that’s what we’d call an awesome deal! These rates were available on Expedia, with a holiday home starting date within the next year. Prices and availability are subject to change and additional terms apply.
Where can I find a Windward Side car rental if I am younger than 25?
This will depend on the holiday home car companies that are in Windward Side. They often have different age policies. If you’ve found an outlet that does cater to drivers under the age of 25 bear in mind that additional fees may apply. Conduct some research into any extra charges before collecting the vehicle.

Information on Car Rentals

 
Popular Car Rental Types:
Hire a SUV, Economy, Luxury, Full Size
 
Car Rental Suppliers Available:
 
Today's Best Car Rental Offer:
 
Second Best Car Rental Deal:
 
Third Best Car Rental Deal:
 
Airport to hotel transportation:
Airport Transportation