Florida - Miami / key west trip

So the wife and i are planning a Miami / key west trip for maybe the first part of June in 2012. Trying to take advantage of my credit card points.
I have enough points on the American Airlines card to fly free. I was thinking of flying in (AA to FLL?) on Monday and staying the first night in Miami.
Again we have many points on priority club and Marriott, but I also have enough for a one night stay with choice or wyndham - so Monday’s one night stay I have a few possibilities - maybe Wyndham Garden Hotel Miami South Beach, Days Inn and Suites Miami/North Beach Oceanfront, Courtyard by Marriott Miami Beach South Beach or Courtyard Miami Beach Oceanfront any insight on any of these?
We would rent a car at the airport and drive to key west on Tuesday. I understand it’s about 4 hour drive, but this should not be a problem for us. I was thinking about renting a convertible, prefer mustang over Sebring. Last year when I was checking summer prices it looked like about $425/week from dollar was one of my best deals. I also saw payless had a ford taurus for $ 161.67/ week special, but I have been unable to duplicate this. I’d go for this to save the $300 and live with the taurus if I could get it. Any suggestions on getting a deal? Looks like it would be better to rent by the week than by the day. I also have an amex card, does this get me free insurance?
Plan to stay in key west tues - thurs – maybe at Crowne Plaza : KEY WEST-LA CONCHA and then driving back on Friday and spending fri and sat back in Miami and leaving Sunday.
i was looking at the Crowne Plaza - Z Ocean Hotel South Beach Miami for the fri and sat stay.

for the Crowne Plaza : KEY WEST-LA CONCHA, do you think i could get points stay here or will they not be available in June? how early can i book? I have my pc chase card so i would be platinum, so are there any fees other than parking (Self parking: USD 20 per night) w reward night and plat? Got a reply that parking may be free with platinum status. Any other resort fees or taxes I may have to pay?
I have the same questions for the Crowne Plaza - Z Ocean Hotel South Beach Miami for the fri and sat stay. do you think i could get points stay here or will they not be available on the weekend?
Any comments or suggestions? Should I stay longer in key west with less time in Miami?
We are middle aged and not big partiers just want to take in the sites. Any suggestions on things to do, places not to miss?
Thanks for looking.

Can't answer questions about the hotels as I stay primarily in Hilton's.

Key West is a very small place. I mean very small. The four days would probably be enough unless you want to do some day boat trips from Key West.

Drive first day taking your time and stopping for lunch on Isla Morada or any of the other Keys. Wed, Thursday doing all the Key West stuff. Friday leisurely drive back to Miami/Ft Lauderdale.

There is a lot to do in Key West if you want to be busy but there is a lot not to do also. People watching is a great pastime there.

There is tons to do in Miami/Ft Lauderdale; enough to keep you busy a lifetime.
It really depends on what you are looking for.

Just a few quick pointers. First, CP Key West La Concha is a dive, small rooms on the very noisiest part of Duval Street.

Break up your drive northbound or southbound between Miami and Key West with a night in Islmorada. Cheeca Lodge is a world class resort there and for a more affordable option, "The Islander" is great. Islamorada is a very laid back, old Florida experience with coconut palms as high as found in the South Pacific.

Worldspan

I have stayed at both Courtyards in Miami Beach. the Oceanfront one is nice, but pretty far north if you want to hit south beach. Cab is like $10-12.
The one in South Beach is okay, nothing spectacular, but is centrally located to Lincoln Road mall and other South Beach sights. Both have expensive valet costs for car parking.
Ideas for the drive down to the keys along with some Miami suggestions can be found in this thread. (http://www.flyertalk.com/forum/florida/1239914-ideas-family-trip-miami.html)

thanks for the replies, please keep em coming. looking at the aa flights, we may change from wed. - tues. spend first night in miami, stay thurs, fri and sat in key west and then sun and mon night back in miami. i was thinking about flying into fort lauderdale, but now it looks like i could get better flight times in miami and not have to drive to fll. does it matter much which airport i use?

Have you looked at flying directly to Key West? Stay there, no car needed hence no parking charges, then rent a car and do the drive and spend a couple of days in the Miami area seeing those sights? Could fly out of Miami/Ft Lauderdale or drive back to Key West.

If you are just going to Miami as a way to get to KeY West there may be other options.

Alonzo's Half-Price Happy Hour ( 4.00-6.30pm ).

Simply the very best deal in Key West.

And the Margaritas are fierce.

http://www.alonzosoysterbar.com/page9/page8/page8.html

I'll second the La Concha thought.
If you're not drinking or boating, two nights is probably best. For relaxation, and lower prices, find another spot in the Keys for a couple days of relaxation as Miami and KW will be busy.

thanks for the replies. think i've tied it down a little more. plan on staying at the Courtyard Miami Beach Oceanfront the first night. driving down to key west (plan on taking the whole day, no rush) and staying at the La Concha for 3 nights. talked to them and i'm hoping i can get the newly renovated rooms on the 6th floor and no charge for parking. come back agin in no hurry and stay another 3 nights at the Crowne Plaza - Z Ocean Hotel South Beach Miami. as i said in the op i'm trying to take advantage of my credit card points, so all these stays are free with the exception of parking in south beach which comes to $29 - $32/day.
AA flight to MIA works better with the times of flights. still not sure about which rental car place to use. sixt gave me my best price for now on a mustang convertible ($360/week) when i emailed them direct, but i plan on keep checking at http://www.carrentalsavers.com/florida-car-rental.html as it looks like prices my drop the closer i get to time to leave.
thanks again and keep the comments coming.

thanks for the replies. think i've tied it down a little more. plan on staying at the Courtyard Miami Beach Oceanfront the first night. driving down to key west (plan on taking the whole day, no rush) and staying at the La Concha for 3 nights. talked to them and i'm hoping i can get the newly renovated rooms on the 6th floor and no charge for parking.

I have stayed at this property three times. Personally, I enjoyed it as i'm one who likes the noise below and want to be close to the nightlife. All three times, I stayed using points and as a platinum member, I was also upgraded each time. Fabulous room on the second floor with a long, wraparound balcony. If you have status w/IC, you may be able to talk them into an upgraded room.

they seem very nice at la concha. they promised me an upgrade, but i'm not sure if it will be one of the newly renovated rooms on the 6th floor i asked for or something else. iin on the avis std suv deal so $225 after coupon for a Standard SUV Chevrolet Equinox or similar is the best thing i have so far.