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Car Rentals in Top Destinations. ; Road Trip from Miami to Key West - Extended Trip Follow this road trip itinerary which takes you through Key Largo, Islamorada en route to Key West and the Southernmost. The cheapest time to rent a medium car in Jacksonville, the United States is in September. Also read 5 reviews of National in Jacksonville & find all National pick up locations in Jacksonville. As the world’s biggest online car rental service, we specialize in finding the cheapest car rental deals from major brands such as Hertz, Avis, Alamo, and Budget. Depending on the size of the family, that could mean anything from a full-size vehicle to an SUV. Woodbridge Potomac Mills Rd. com account. You will have to pay an under 25 fee. September is the cheapest month to rent a small car in Jacksonville, the United States (~$41/day), while the most expensive month to rent that same car type is March (~$60/day). Enter location. 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