Deal or no deal?
 

A travel agent quoted me $4880 for the following:
Air for 3 from Richmond, VA to Maui then from Maui to Honolulu then back to Richmond.
6 nights at one of the Outrigger properties in Maui--in Lanaii I believe?
4 nights at the Otani in Honolulu
a rental car in Maui
tax and transfers included.

This will be our first time to Hawaii and while I'm a pretty savvy bargain travel shopper, I don't know about negotiating this many hotels and flights on my own.

Sounds like a good deal to me.

Round trip airfare for three to Hawaii and inter island, a rental car, and accommodations for 10 nights for under $5000?

Well, you can easily check airfare prices on the airline web-sites or through sites like Travelocity, Expedia & Orbitz. You can get hotel rates on the Hotel websites and maybe even the travel sites mentioned above, and rental car rates from the car rental sites (Hertz, Avis, National, Dollar, etc.). Do a google search to fine the particular websites you want. You are really only staying at 2 hotels so that shouldn't be a problem. When getting your on-line airline quote use the "Multi-City" function and plug in your dates of travel and cities.

Doing all of the above should take about an hour or so of your time and will give you an idea if the rate you've been quoted is competitive.

Depends on what kind of room you have at each place.

I picked Sept 10 to 20 as the dates of your trip. Airfare is $833 per person, so $2500 for three.

Sept 10 to 16 at Outrigger Aina Nalu Resort in Lahaina is available at travelocity $167 for a 1BR garden view. Or an average of $195 for a 2BR 2BA suite (that's $233 per night with 6th night free)

Outrigger Royal Kahana is $136 to $155 for a "studio" room.

September 16 to 20 would cost between $128 and $320 per room at New Otani Kaimana Beach Hotel in Honolulu. These are 1BR hotel rooms.

So figure $200 per night for 10 nights. That's $2000.

Car in Maui between $200 and $300 depending on size. That's $250 including taxes.

For the 2BR in Maui, the taxes would be $160. Figure $140 for the New Otani.

Guess of $50 for transfer in Honolulu? Maybe double that?

2500 air
2300 hotel with taxes
----
4800
300 for car in Maui + HNL tranfer
----
5100

If you got the least expensive rooms then the cost would be around $4500 total. That's without shopping around, just checking travelocity for each item (air, hotel, car) separately.

We're traveling to Maui / BI in June from Richmond. I found that booking everything separately was better for us. TA initally quoted us $6,000 plus and I was able to book everything myself for $5,500. For me, planning the vacation is a lot of fun, but it may not be for you. Good luck with your decision.

FYI the Outrigger Aina Nalu Resort is the former Ohana Maui Islander finally remodelled and now sold as condo units. Its location means you can walk anywhere in Lahaina but some units would be too close to Rte 30 IMHO.
http://www.outriggerainanalucondo.com/index.cfm