Hello,
My Wife and I want to celebrate her birthday and my retirement on Maui. We would like to stay for 2-3 weeks if the right deal came along. What would you good people suggest and where should I look to pull this off. For now January works better than Feb. or March. Not totally set in stone because I'd like some good weather I'm looking forward to suggestions and advice. thanks in advance, Randy

What do you mean by the "right deal"? Are you trying to find a package with air & hotel & car together? Or just a good rate on a hotel, resort, condo, private rental?

Maui weather is historically similar in January and February, lows 50F and daytime highs 70s.

I could try to do all separately, but if there's a decent pkg deal, I'm up for that too. What would be a good price for air from Milwaukee, then lodging, and car

Are there houses or condos better to rent than staying in a hotel for 2-3 weeks?

DW and I had a good deal on a condo in Kehei in May. It was across the street from the beach. In January you will probably pay a little more than we did in May. We bought our airfare online separately. Keep shopping for a couple more weeks before you select your condo.
There is a car rental place in Kehei that will come to pick you up from the airport. There are some expensive cars at the airport. Do not under any circumstances use Kimo's car rental. They are worse than Rent-A Wreck.

Winter on Maui is very popular with people booking a year in advance. You may have trouble finding a good condo, so it may work better for you to book through Costco or similar. Very few hotels there. A good price will be whatever you can find!

For car rental Discount Hawaii Car rental is reliable.

For that long a period of time I would definitely rent a condo, even if you do not cook much it is nice to have the extra space, plus a fridge to store drinks, snacks and leftovers and a microwave to heat pastries and leftovers.

Are there houses or condos better to rent than staying in a hotel for 2-3 weeks?

Sure, those are available. But it's a matter of personal preference if you like renting a condo better than staying in a hotel. One isn't "better" than the other options.
Lahaina Shores is kind of an in between (a condo/hotel) that my family really enjoyed, on the edge but walking distance into the town of Lahaina.

You are late looking for a condo on Maui for this time of year. All the usual snowbirds are there, along with people coming for Whale Season (January - March). You might start by looking at what Costco has in the way of a package. Here are two agency sites that I like for South Maui: www.mauiownercondos.com www.crhmaui.com Chase & Rainbows is good in West Maui. You can certainly try www.vrbo.com as well.

Yes, a condo would be my choice -- actually has been our choice for twenty years, since we bought at Maui Kamaole in South Kihei on Maui. (We use our place Jan. - Mar., coming from north of Chicago.) Obviously, we like that complex, but you'd be good in either South Maui or West Maui (up to Napili/Kapalua, where *I* find it too windy in winter). Condos are generally less expensive than hotels. They also allow you to save by eating 'in' some of the time. You can pack lighter with laundry facilities in a condo. "Home from Home" -- but on Maui! Few condos charge resort fees or parking fees, as hotels almost all do now. (You might use a condo while touring the island, then splash out at a resort hotel for a few nights. You might also consider staying a few nights Waikiki before Maui. )

United has nonstops from ORD to both HNL and OGG. AA is starting one to HNL towards the end of this year. We have also used AA via DFW to get a wide-body aircraft on the long leg. Southwest Airlines is entering the Hawaiian market soon, too.

Forum members can help more if you can tell us your lodging budget per night. You are probably looking at minimum $200/night, plus 14.42% taxes and a one-time cleaning charge. Skip any ads that claim you will be kept cool by fans; you'll want air conditioning!