Best $500/night Maui Room & get:
 

Great Oceanfront Room
Romantic (we will not have kids with us)
Not too remote

So you're only concerned with the room?
Location, service, food, pools, beaches, type of clientele are unimportant?
As for the room, what are the keys? Size, quality of furniture, type of bed, etc?
If size is all that matters, Kea Lani has the largest rooms for the dollar of the better Maui hotels.
If bed quality matters a lot, then the Four Seasons is better.
If you want access to local nightlife then the Hyatt has a location advantage, etc.
Depends a lot on the particulars.

Ted,
I do believe she pretty much stated what she wants:
Money - no object
Romance
Great oceanview
within reach of civilization
I don't think the pool, the restaurants or the size, at least of the room :) really matters to her.

I disagree.
There are numerous hotels which fit Nancy's criteria, but some of those hotels will appeal to certain people but not others.
Example: Ritz Carlton, Kapalua Bay, Hyatt, Sheraton, Four Seasons, Kea Lani, Grand Wailea and even the Renaissance will be some people's definition of the perfect hotel for room/location/atmosphere.
But some people detest certain hotels on this list, but love others.
Without additional info on Nancy's specific desires, recommendations aren't all too specific for her needs IMO.

Money does seem to be an object: $500. The other conditions are view (oceanfront) and that it is romantice. What isn't clear is whether Nancy means actual oceanfront or full oceanview.

For oceanfront, the only one I can think of right now, besides various condos, is the Renaissance Wailea that has the separate oceanfront wing. You may be able to get that for $500 a night.

The other hotels have more of just an oceanview. The top three that come to mind are the 4S, Kea Lani, and Ritz. However, to get a full oceanview room will most likely run you more than $500 a night.

What is not clear about "great oceanfront"?
The rack rate for The Sheraton Maui's ocean front rooms (not ocean view) is $570 (and you can always do better than the rack rate).

This is Nancy03

The reason I asked this question is because it doesn't look to me like I can get an oceanview/front room for $500 at the 4 Seasons, Grand Wailia or Ritz. I don't want to stay in a garden room over looking the pool/mountains. I have mountain/waterfalls views during another part of my trip. I hope to sit on my lanai or balcony in the morning and enjoy the surf and view. I don't care at all about it even having a pool as I prefer to sit or walk the beach. I would rather have upscale adult and not "Disney type" qualities. I'm not concerned about the food - unless I have to eat there. So therefore I don't want it to be too remote that we can't walk or quick drive to eat elsewhere. And I hope for $500 a night you will guide me towards a place with rooms of good quality (amenities, bed, room size, clean).

Very few rooms at the Four Seasons are truly oceanfront, and those that are cost far more than $500. You might be able to get an ocean view room for approx $500. These will have a partial ocean view. The alternative would be the Kea Lani, but I'm not sure what their current rates are. I would avoid the Ritz because of its remote location. The Wailea area has consistently great weather, great beaches, and enough civilization for access to good restaurants, etc. The area near Lahaina is too crowded and overdeveloped for my taste. I would take the best room I could get for $500 at the 4 Seasons, which, in my opinion, is the best overall hotel in Maui, with the best services, facilities, etc.

puddy gave an excellent sugg...the Renaissance at Wailea. Understated elegance. I would love to stay there on my next visit to Maui.

AAFF, glad to see you visit the Hawaii board.

Never been, but going soon with the AA first class sale going on. $1100 from east coast. Got the flight, working on the hotel! :-)

Great deal AAFF!!! Are you planning to stay on Maui only or visiting other islands as well?

Good luck selecting amongst all the excellent hotel choices (particularly on Maui)! I can't wait til I hear your opinions on this board!!! 8-)

well, I'm flying into HNL, but willing to try anything once, so any suggestions?
Hawaiian Airlines has a great deal for AA FFs. 5K miles for a round trip to any island, so GO BIG bluefan :)
I live on a great beach, maybe not as beautiful as some of the Hawaiian beaches, but still... you get the point, I hope, so beach front is not the most important feature. What is? Volcanos, black sand, rainforests, etc..etc.., and although I'm somewhat pass my prime, some nightlife would be great :). Great restaurants always make my day as well.
Work it out bluefan, 8 days in Hawaii for a novice....

Due to all the sage advice you provide, I'd be more than happy to oblige and provide for you what I imagine might be a fantasy vacation custom-tailored for you.

If you arrive in HNL in the morning, arrange for a 4 hour visit to Pearl Harbor. If not, skip it and fly immediately to Maui. Apologies to Kal (and other Kauai fans) and BI fans, but y'all know that Maui is a terrific island for the first-timer. It's got almost everything you're looking for AAFF: black sand beach, rainforests, nightlife and a great variety of restaurants. The only thing it lacks is an active volcano but there is Haleakala.

Get your rented convertible and make a beeline for the Four Seasons. Go relax and indulge yourself in top-notch service. For the first three days of your stay, I would simply soak in the sun at the wonderful beaches down there (e.g. Makena "Big" Beach, Polo Beach, Wailea Beach), get some shopping in for the wife at the Shops at Wailea, take some sunset strolls along the scenic beach walkway over to the other fine resorts and dine at Nick's Fishmarket (Kea Lani), Humuhumu (Grand Wailea), and Spago's within the 4S. Grab some lunch at places like Maui Onion (Renaissance) or the Tommy Bahama café at the Shops. I would limit excursions to the following: visits to Haleakala and La Perouse Bay, morning trip to Molokini if you enjoy snorkeling, and a helicopter ride.

On the fourth day, I'd pack and check out of the 4S in the morning for the Road to Hana. After passing Paia, check out Ho'okipa and the windsurfing there. Take your time along the coastal road and make several scenic stops along the way (the book Maui Revealed is an excellent guide). One of my favorite stops is the end of Nahiku Road (the coastal view from there is awesome and there's a quaint waterfall pool nearby). Also check out the Blue Pool. Make sure you packed some lunch and go picnic at Wainapanapa Park where the Black Sand Beach is. Then stay overnight at the Hotel Hana Maui. I believe they also provide a shuttle to their facilities at Hamoa Beach, one of my favorites. The next day, I'd check out the Venus Pool and the nice road-side waterfalls before arriving at O'heo Gulch before the throng of day-trippers. If you're up for it, make the 5mi RT hike to Waimoku Falls. You won't regret it. Relax at the pools of the Gulch before taking the road along the bumpy backside. Just make sure to get to Mama's Fish House in Paia before sunset. It's my favorite restaurant in the entire world (for now). Excellent local-caught fish and the best mai tais. Try the ahi poke and mango cerviche for appetizers. I forget the name of it, but the buttery swordfish is to die for.

Last three days I would spend at the Ritz Carlton in Kapalua or the Hyatt at Kaanapali. Kaanapali is a great area to wander around (although it can get crowded) with its nice beach walkway and there's Whaler's Village. The Hula Grill there is a terrific beachside restaurant with a lively atmosphere. Dinner at the Banyan Tree at the Ritz or the Swan Court at the Hyatt would be elegant options. If you like sushi, definitely head to Sansei in Kapalua, and don't forget to see the sunset ceremony at Black Rock.

Lahaina is the historic town that you must visit, even if it is touristy. The banyan tree as well as the old ships in the harbor are pleasant sites and there's plenty of fabulous dining options. Gerard's is an excellent French restaurant. A lot of people here tout David Paul's Lahaina Grill, I'o, Kimo's, Longhi's and Pacific'O but no visit is complete without going to Cheeseburger in Paradise...a very fun place. Other entertaining evening options would be the Old Lahaina Luau or Feast at Lele as well as Warren & Annabel's magic show. There's several bars and a few clubs as well.

During a stay in West Maui, I would try to fit in a drive (clock-wise) around the northwest coast with stops at the Nakalele Blowhole and Olivine Pools (but they involve short, steep hikes) before making your way to Iao Valley. Don't fret about the narrow roads...your drive along the Road to Hana will have somewhat prepared you for this trip.

Although the suggested itinerary might involve more moving around then you might like, it at least allows you to maximize your stay in the top 3 areas of Maui. There you have it AAFF with no fees charged. Maybe I should become a travel agent. 8-)

Thank You bluefan :)
With the exception of buying gifts for the wife, I will follow your itinerary. If any one suggestion is not what it is suppose to be, well.....
the whole Fodors board will hear about it. Do you see the possible ramifications? This will be your last chance to change any part of the itinerary :-)
No matter what, I will visit Pearl Harbor. History is my little secret hobby.
Thanks again!!!

That's an excellent itinerary, bluefan.
Covers all the important bases.
Doubt you'd ever get a complaint from anyone following that advice.

No problem AAFF, and even if you come back with differing opinions, I'd still love to hear them!!!

Thanks for the kind words rwilliams. I thoroughly enjoyed your comments (pros and cons) re Jumby Bay and Cap Juluca on the Carribean board. Great stuff!!!

The Kapalua Bay Hotel has a Romance Package with oceanview rooms for under $500. Check out the list of accommodations at this website - http://www.visitmaui.com/index.html. Kapalua is just a short drive to Kaanapali and Lahaina.

Also, my niece got married on Maui last month at the Diamond Resort in Wailea. Nice Japanese style property with a fabulous location. They have Deluxe oceanview rooms for $340.