About Us

Located on beautiful Siesta Key, Peppertree Bay offers all the luxurious amenities you’ve come to expect from a vacation! Need help to plan your month-long 4-week vacation? Read our blog article for help: How to Plan Your Very Own Sensational 4-Week Beach Vacation.

Peppertree Bay is located on the island of Siesta Key. We are right next to our own private Crescent Beach just south of Siesta Key Beach. Our monthly rental properties have a minimum stay of 28 days and our units are fully equipped with a modern kitchen and your own private lanai.

Peppertree Bay is a family-oriented vacation rental resort that has lasted through generations of families who have been returning to Siesta Key for decades. We provide luncheons and game nights, which include card games such as Bridge and Mahjong. We also have two heated pools, tennis courts, BBQ grills, a fitness center, and two clubhouses. Some of the guests will rent out one of the clubhouses and have parties for friends and family.

Our guests say that Peppertree Bay has a quiet, resort-like feel that you can’t find anywhere else on the island. Want to find out more? Check out our F.A.Q. page.

Our properties include spacious two-story townhomes, garden units, and exquisite high-rise condominiums. We have Bayside condos, Gulfside condos, and even have condos for sale.

Keep in the know with us at our Facebook page for Peppertree Bay’s upcoming events, learn more about the community, get in touch with others, and share your own photos!