The City of Maldonado is only a few minutes drive from Punta del Este. You can get a good view of the peninsula, which is 15 blocks long, from there.
Its climate is mild all year round. In the winter, temperatures reach 10º C, whereas in the summer the thermometer marks over 25º C and many times it goes over 30º C.
Maldonado is a pretty town and a wide white sand beach.
Punta del Este
"Malibu of the South America"
Located on the Southern Atlantic at the mouth of the World’s largest estuary, lies Uruguay’s Punta del Este.
Punta del Este is the playground of South America’s rich and famous. It has beautiful beaches, and beautiful people. Of the people I have met there, easily 80% were well to do Argentines or Brazilians.
I have been there is high season and low season. (High season runs from about Dec 15th till March 31st) During high season the city is totally packed. Rooms are hard to come by unless reserved well in advance. This is the place to be seen, but be ready for crowded beaches, lines at restaurants, and hard to find taxis.
During the off-season, the city is pretty much a ghost town. It is hard to believe it is even the same city. If you are not totally a water person, there are some great deals to be had on hotels and services before and after the high and mid seasons. Many hotels offer discounts of up to 50% off. I have to say that visiting during the shoulder season was more relaxing for me. The beaches were empty, seats at the year round restaurants were east to come buy, and other specialty services, such as jeep safaris, boar hunting trips, or sailboat rentals, were available as opposed to during high season.
For the gambling fools like me, there are a few casinos in town, but the only one worthwhile is at the Conrad Hotel. The Conrad Casino is the only privately run casino in Uruguay. The service and comps are far above the state run facilities.
For resources about Punta del Este, I found a very helpful site.