While we stayed at the Pineapple House with conventional hotel rooms, the other half of the resort contains 27 villas. These private residences are perfect for traveling with family, groups, or those desiring privacy. Villas range from 2 bedrooms up to 6 bedrooms and everything in between. Amenities include a housekeeping staff, a made-to-order breakfast in your villa, a private pool (in most) and open air living spaces.
As you can see the villas could be considered the ultimate hideaway. Check out Round Hill’s website to read about some of the celebrities who have stayed here over the years. For example, “How Stella Got Her Groove Back” was filmed in villa 11 and songwriter and producer Oscar Hammerstein owned villa 12. It’s also where he allegedly met Maria von Trapp and “The Sound of Music” was written. Possibly the most famous guest might have been President JFK and Jackie Kennedy where they spent their honeymoon in villa 10.
While I didn’t have the opportunity to visit any of the more historic properties, I did have the pleasure of touring Villa 20. The largest on the grounds and recently renovated, this 6 bedroom property features almost 9,000 square feet of well-appointed rooms along with 2 pools. The villa was made to entertain or to set the scene for the perfect wedding. Among my favorite touches were the swinging beds located on one of the many patios. It would be beyond dreamy to curl up with a good book or nap the day away.
Each villa is individually owned with it’s own unique decor and style. I hope to someday return and experience one for myself! Until then I have these gorgeous pictures to remember them by — XO A