Longer stay on Maui.

[beaglebuddy]

http://honolulu.craigslist.org/mau/sub/
http://honolulu.craigslist.org/search/sga/mau?query=windsurf
You need to do separate searches for gear using the words windsurf, windsurfer, windsurfing and sailboard, there is tons of used gear for cheap.

[dsgrntlxmply]

Vacation rentals may now be less available on Maui by comparison with former times. The county brought in a permit program with several tiers, with a limited number of permits available within each tier and so-called planning area. Whether this was more in response to neighbor concerns with transient occupancy, or being in the pocket of big resort property interests, remains to me an open question.

Some formerly available places might still be available, but trying to fly under the radar and less openly advertised than formerly.

All I know is that the place that I used to stay, I could not reach to book, and ended up instead at an OK but less agreeable decaying old resort hotel in Kihei, for more money.

[justingordon]

You should look in craigslist for Maui. Look for long term, furnished rentals. If somebody has a gap, you might be able to fit in.

If you find a great deal on an unfurnished rental, there are some furniture rental places.

Some of the off-brand, local rental car companies will also do several month leases. If you have time, it's worth it to buy a used car and then to sell it, with the transfer date close to your departure date.

Good luck. If you come to Maui for more than a few weeks, you'll:
1. Get a feel for what it's like to live like a local.
2. Be sure to get a variety of conditions.
3. Get a chance to learn more sports, so that every day is an epic day.
4. Make some local friends.

Naturally, I highly encourage you live close to Paia if you like windsurfers and windsurfing. There good options on the towns that border Paia as well, such as Haiku, Makawao, Pukalani, and Kula.

Other areas like Keihei, Wailuku, Kahului, etc. will not have the same windsurfer and country town resort vibe. My family really likes the Sprecks area of Paia, as it's only a 30 min drive to the south shore, 3 min to Paia, 10 min to Kahului, etc.

Good luck and aloha,

Justin

[keycocker]

Great advice from Justin. Most sailors on Maui only stay in Kihei if they have no other options.
The conditions are such that many sailors who live a block from the sea will only sail there once a year, preferring to drive to the Paia area on the north shore.
You will find some month deals in the summer in furnished. Home on sublets and temporary on Craigslist. These are folks going over to the mainland in summer. The deals we made from these ads were far and away the best deals.

I called one lately three bed furnished,food in the fridge, pet the cat, utilities paid, for $1500 month. She asked if I needed her car for a few dollars more.

[uchida]

Try VRBO.com (Vacation Rental By Owner). You'll need to have some idea as to where on the island you and yours want to spend a month. I prefer the Kihei area. It's very family oriented with lots of great beaches, a variety of restaurants ($-$$$$) and shops and it's centrally located to Kanaha, Lahaina etc. I can get a studio condo for $45-$50/nt based on a 3 week stay. A month stay should be even cheaper. The sailing there isn't the north shore but can be quite good at times.
I've been renting a Maui cruiser from Frank's Friendly Autos for years now. Cheaper than Avis, Dollar and the rest. They are not new but well maintained. The biggest plus is that the car is waiting for you in the airport parking lot when you arrive and you leave it in the same lot when you depart. You don't have to stand in line at a rental car agency with everyone else that came over with you on your flight. Plus Frank is a great guy and I'd rather give him my $$$ than corporate america.
Renting equipment seems to be based on your preference. JP vs Naish vs Goya etc. The cost seems to be fairly similar at most of the shops. Seems everyone has a favorite. I've been treated well at all of them. They also sell their rental gear during certain times of the year. I've gotten some great deals on all kinds of gear in Aug and Sept.
I moved all my gear to Maui and store it at Extra Space Storage. I've use the one in Kahului and the one in Kihei. It's safe and convenient. I use to use Second Wind when Ralf owned it. ESS in cheaper and way more convenient. I understand that several people have rented a large unit and are sharing the cost. Post an inquiry here if interested.
If you decide to buy a vehicle on Maui, I understand there is a place upcountry that will store it and even charge the battery for around $1/day. There are a few sailors at Kanaha that store vans with all their equipment in it there and they haven't had any problems. Again, if interested post and inquiry.
Hope things work out for you. I'm envious. I'll be doing the same in the not too distant future. 2-3 months in paradise will be wonderful!