OK, here is a summary of what I see for options. I suspect the most likely Priceline Resort property in Kapaa-Lihue-Koloa is the Marriott and might require a bid of about $120 or $130. The Hyatt may be available through Priceline but would be a much higher rate and you could always end up with the Marriott (and an overbid). If you wanted true luxury and a really special resort, the Hyatt would be the one, but it is PRICEY! I think it is the 5* property that is available through Hotwire and I see $269/night for your dates for it. (Starts at $338/night on the Hyatt website, though) The 3* properties on Priceline for the same zone probably include the Radisson and the Sheraton. They would probably be available for a bid of about $100. The Radisson, Sheraton and Marriotts are all nice properties, but you might be disappointed if you wanted a really super-luxurious resort. They are decent, but the rooms (and views!) can vary quite a lot. Still, you are most likely to be satisfied, even if not completely thrilled. There might be some additional charges for parking, but these usually aren't high and include valet service, if you wish. I don't think most of them charge a resort fee, but you could give them a quick call to ask. I am pretty sure the Radisson does not charge a resort fee. There are 2 and 3* properties in Princeville on Priceline, but I think you might find these feel a bit out of the way (unless that is what you want?) and I would think they would be $70 - $90 for a winning bid, but that is just a rough estimate. Haven't really researched it. On Hotwire, I do see a 2.5* condo for $87/night, but this is only useful if you really want a separate bedroom and kitchen. Personally, I would make the decision this way - where do you really want to spend your time? If you want the total resort and luxury experience, and plan to spend most of your time around the hotel itself and its pool and want full-service everything, then you probably want the Hyatt. But your budget says you should try for the Marriott. This would be the Resort category and I would bid it on Priceline as outlined above. If you want to be able to spend half your time at the hotel and you want some decent service but don't need all the luxury, go for the 3* properties through Priceline. However, there is one other option. If you know you are going to be out and about and exploring the island and its beaches and eating in different areas each night, then maybe you could go for the budget option. The 1* property on Priceline may be the Kauai Sands and it is humble, but clean and well-located. You can walk to a lot of things and it is a pretty beachfront area and a short distance to good swimming beaches (Lydgate Park, for example). There's probably no room service and no one will bring you drinks by the pool, but you may be able to get a room here for $45 - $55/night. I believe it is the same one that shows as a 2* on Hotwire for about $56/night. My personal favourite would be to book 4 or 5 nights at the Kauai Sands (while I am busy exploring) and then 2 or 3 nights at the Hyatt (for kicking back and enjoying the BEST of the rest). But some people would never want to stay at the Sands and would never want to spend the extra money for the Hyatt! Still, if you combine them this way, you don't spend much more than you would for the intermediate properties... for example, $200 for 4 nights at the Sands plus $800 for 3 nights at the Hyatt gives you a total of $1,000, but you would spend about the same for 7 nights at the Marriott. But this is my own idiosyncratic take on things, and may not be right for you! Feel free to ask me more about why I would do things this way, if you wish. Check out the reviews on TripAdvisor.com to help narrow things down. As for cars, I would try bidding Priceline - about $18 to $20 for a full-size and $22-24 for a premium, but make sure you check for special weekly rates through the usual sites first. And thereuare, feel free to add any additional wisdom or let me know if I am missing anything.