Anonymous wrote:As a regular vacationer at all these places, no, the Homestead is not at all similar. There's a reason the rooms at the Homestead start at <$200 compared to $300++ for Sanctuary, Cloisters, Breakers. The Homestead is typical four-star Omni property. The other three are true luxury five-star properties.
Yes, the Breakers is also a historic, older building, but not nearly as antique as the original part of the Homestead. It's gone through some serious renovations over the years and the rooms are up to modern standards. the Cloister and the Sanctuary are both actually new buildings (about 15 years old).
All have great facilities and activities - more broad choices at Kiawah and Sea Island, but the cabanas at the Breakers pool are hard to beat for families.
This is a good summary. OP, I too was pretty disappointed with Homestead. Having been to the Grand Hotel on Mackinac Island, Greenbrier, Hotel del Coranado, etc., I thought it would be like those, and it most definitely is not.