Your tag implies you are searching for a "warm water" area. If that's the car and you want to be on the "east coast" you really have to go as far south as you can. That means Florida or possibly Georgia. the one caveat is that in May, the water anywhere is not going to be all that warm.

You also wanted some place that's "easiest for us all to get to" but you didn't say where you are traveling from.

So, knowing only the few facts you've given I'd suggest you look at areas around Miami Beach. While that's a populated area there are some resorts that will give you the illusion of being secluded. you could also check out places in the Florida Keys - your group can still fly into Miami then it's a relatively short drive to some of the northern Keys.

If you want to risk having slightly "cooler" waters look at Amelia Island (near Jacksonville, Fla) or perhaps Sea Island Georgia.

Just all fly to the caribbean somewhere.

Quiet for a WEEK????

For a couple of days maybe.

Consider Puerto Rico or St. Thomas, also

I second the vote for South Beach... amazing beach, spas, shopping, restaurants, and plenty of places that are "cougar friendly"... or just crash at the pool...

despite the image that South Beach is all Party, there are plenty of places for a quiet girls trip...

I would recommend a www.vrbo.com condo to accommodate your group over a resort hotel unless you have a bigger budget...

What about renting a beach house in Tybee Island, Georgia? Then you can spend a few days exploring Savannah (a short drive away) and also get your beach time in.

I agree with spiribulldog. The Carribean is the place for this special celebration! And prices for accommodations in May in the Carribean will often be less.

Oops. Misspelled Caribbean, wish we had an edit button.

I've enjoyed quiet visits, with some activity as well, to Grand Cayman, Turks and Caicos, and Puerto Rico.

South Beach or Key West would be lots of fun. Also, I agree with Puerto Rico.

I'll throw Naples into the mix - Look at the Ritz

Islamorada, Florida Keys has just what you are looking for!

My recommendation is Siesta Key, Florida. Easy drive from Tampa (or even easier from Sarasota), plenty of condos to rent, beautiful beach and lots of fun restaurants in the area!

Charleston and Isle of Palms. Or Sea Island or Kiawah.

I think the bottom line to your question is there are a lot of places that would fit the bill of "quiet, pretty, pampering, warm, and near water" in May from the Caribbean to various parts of Florida from east coast to west coast (of Fla.) The next issue is budget and what kind of place you want. A condo of some sort would allow you all to share. Friends of mine have stayed at this place on Ana Maria Island and loved it but I think the largest units they have are 2 bedroom 2 bathroom.
http://www.tortugainn.com/index.html

I agree with garyt that looking on vrbo.com is a good idea unless you have your hearts set on staying at a hotel or spa. You may find using the trip planner on wunderground.com helpful to look at historic temperatures for the dates you're planning anywhere in the world. http://www.wunderground.com/travelplanner/index.asp

My suggestion is Sanibel Florida. Warm, beautiful, quiet, a great spa, delicious restaurants. It's known as the shelling capital of the world. You can take a day cruise with captivacruises.com I've done it several times. It's a beautiful day. You may be lucky to see pods of dolphins following the boat. Get a drink, sit back and relax with friends. I can also recommend Kenoyer Realty for a condo. We get the same one each year and love it.

Punta Cana has some nice discounted deals going for that time of year right now.

Seagrove Beach/Rosemary/Seaside in north Florida is lovely that time of year and is quiet and quaint. We usually stay at www.OneSeagrovePlace.com but I think the largest units are 2 BR / 2 BA. www.vrbo.com has many other options in the area available. The beach there is so, so pretty.

As mentioned above, Sanibel is another good option. (Or Captiva)

Also, Brasstown Valley or a cabin in the north Georgia Mountains might be nice. Although it is not ON the water, Brasstown Valley has a lake nearby, and on the property there is a spa as well as other activities and the accommodations are very nice. You could all fit in one cabin, I think, not sure.

Cheeca Lodge in Islamorada Florida, or Hawk's Cay ( both in the Florida Keys)

I just returned from the Florida Keys and would agree with the suggestion above.

The hotel we chose, The Moorings on Islamorada, ranks right up there with the most idyllic hotels I've ever visited. They have cottages of various sizes, including a few with three bedrooms. They have a spa, a beautiful beach, and a gorgeous saltwater pool. They will give you new bikes and a barbecue set to use during your stay. You can walk to restaurants and bars. Key West is about 90 minutes away by car.

I've been fortunate enough to have stayed in a lot of great hotels all over the place and this one ranks right up there with the best.