The OP seems to have solved the problem by reserving 2 cars.
Some comments for others:
Some people book flights into alternate airports, both home and Florida, before they research ground transportation. People who don't want to rent a car don't have a reasonably cost way of getting from Tampa to Disney. Sounds like the OP is a family of 6. If they have a vehicle which will sit 7 plus luggage they could ask a friend or relative to drive them.
regarding one way car rentals. I don't agree with some of the points made by regulars.
Sometimes a rental agency needs to reposition part of their fleet. Examples include moving cars from the N to Florida in the fall and moving cars to a Superbowl city. Not only will the agency waive a drop fee but the actual rate may be dirt cheap.
Some places, between Florida locations for example, one way rentals are generally reasonable.
Most places agencies charge extra for one way rentals. They may charge a higher rate (including not allowing discount cards), limit the number of free miles or charge a drop fee. The extra charges offset the extra miles a one way rental is likely to drive and offset the charges incurred in repositioning the vehicle back where it's need. The local agency can't rent a van which was dropped of a the airport. Sounds like the OP was quoted a $250 drop charge for the van but no charge for the cars. The OP said the van rental is $125 per day. It could easily take 3 days before the agency has a customer who wants to drop off a van in the local. The drop fee helps cover the cost of having an employee drive back to retrieve the vehicle or the kinds of discounts the OP suggests the agency offer. I don't know how long it will take before a customer wants to rent a car at Portland with a drop off at Eugene.
Waiting for a last minute deal generally works at MCO. You have many agencies with lots of cars. Making a few dollars might make more sense then letting the car sit.
Waiting for a last minute deal for a one way rental can be a mistake. They agency can't let you drop off the van in another city tomorrow if they have customers who have the van reserved the day after tomorrow. Wait too long and you'll be told the vehicle size you want is unavailable. The agency is better off letting the vehicle sit unrented for a day rather then lose the vehicle for an unknown period of time.
Some comments for others:
Some people book flights into alternate airports, both home and Florida, before they research ground transportation. People who don't want to rent a car don't have a reasonably cost way of getting from Tampa to Disney. Sounds like the OP is a family of 6. If they have a vehicle which will sit 7 plus luggage they could ask a friend or relative to drive them.
regarding one way car rentals. I don't agree with some of the points made by regulars.
Sometimes a rental agency needs to reposition part of their fleet. Examples include moving cars from the N to Florida in the fall and moving cars to a Superbowl city. Not only will the agency waive a drop fee but the actual rate may be dirt cheap.
Some places, between Florida locations for example, one way rentals are generally reasonable.
Most places agencies charge extra for one way rentals. They may charge a higher rate (including not allowing discount cards), limit the number of free miles or charge a drop fee. The extra charges offset the extra miles a one way rental is likely to drive and offset the charges incurred in repositioning the vehicle back where it's need. The local agency can't rent a van which was dropped of a the airport. Sounds like the OP was quoted a $250 drop charge for the van but no charge for the cars. The OP said the van rental is $125 per day. It could easily take 3 days before the agency has a customer who wants to drop off a van in the local. The drop fee helps cover the cost of having an employee drive back to retrieve the vehicle or the kinds of discounts the OP suggests the agency offer. I don't know how long it will take before a customer wants to rent a car at Portland with a drop off at Eugene.
Waiting for a last minute deal generally works at MCO. You have many agencies with lots of cars. Making a few dollars might make more sense then letting the car sit.
Waiting for a last minute deal for a one way rental can be a mistake. They agency can't let you drop off the van in another city tomorrow if they have customers who have the van reserved the day after tomorrow. Wait too long and you'll be told the vehicle size you want is unavailable. The agency is better off letting the vehicle sit unrented for a day rather then lose the vehicle for an unknown period of time.
