Have you looked into Siesta Key in Florida on the Gulf side? I don't think it's technically Key West. We stayed at the Sea Castle a few years ago and it was great. It's right on Crescent Beach, which has beautiful white powder sand and clear aqua water - it reminded me of the Caribbean. It has a kitchen so we saved money by buying groceries and eating there for breakfast, lunches and a couple of dinners at the grill on the patio. There is shuffleboard and a pool on the premises, and you could rent kayaks and catamarans by the hour on the beach plus great shelling. In August, the resort is about 1,200 for the week. You can find some other condo type places on rentalo.com. We flew into Tampa which wasn't that expensive on Southwest (there are deals as low as $120 for a roundtrip flight for August) and rented a car; it's about an hour south. We mostly spent the days on the beach, but we did do one day at Busch Gardens since it wasn't that far.

If you want to do something where you can drive, have you considered Cape Cod? My parents live in Plymouth, which is right before the bridge to the Cape, and it is a very cute town with lots of history - trolley cars, plimoth plantation, plimoth rock, Mayflower replica, whale watching, etc. You can find a bunch of different homes for rent on a weekly basis for $800-$2000 a week on vrbo.com at different beaches or near the harbor. There are other places on there too on freshwater lakes that are nice. Other places that are nice actually on Cape Cod are Falmouth, Hyannis, and Sandwich.

Good luck!

August is tough for what you're looking for. I used to live in New York and we never considered going anywhere at that time of year because we had paradise right in our backyard - Long Island Beaches. My sister still lives there and she goes to Block Island every summer.

You also have Cape Cod, Bar Harbor, the Outer Banks, etc. The East Coast is fabulous then and you want to go to Barbados?

I live in California now and in August, we would have to choose between Lake Tahoe, Bandon in Oregon, or Victoria in British Columbia as three of our favorites.

Also, a few years ago we went up to Mackinac Island in Michigan and really enjoyed it. We also spent some time on Lake Superior and enjoyed the National Lakeshores, the historical sites on the Keweenaw Peninsula, and the National Parks on the Canadian side.

Good point supercilious.
Cape Cod would be perfect. Stay in Chatham for an upscale, historic town and nice beaches.