MEET THE TEAM

Elevating Your Experience

Ben & Bess Scarborough

Ben and Bess Scarborough are the powerhouse duo behind Elevated Escapes’ smooth operations. As Operations Manager, Ben oversees property management and the virtual assistant team, while Bess manages administrative processes and supports key initiatives. Together, their focus on efficiency ensures every property runs seamlessly and every guest enjoys an elevated, white-glove experience.

Caleb Drake

Caleb Drake is a real estate professional and short-term rental owner dedicated to delivering an exceptional guest experience across the Southeast. Frustrated by the lack of quality property management along the Gulf Coast, he partnered with like-minded entrepreneurs Ben and Bess to co-found Elevated Escapes offering top-tier, stress-free short-term rental management that enhances the entire experience for both guests and property owners.

Stay With Us

Your next vacation is just a click away. Whether you’re looking to escape the day-to-day at the beach or in the mountains, we are here to provide you the relaxing, adventurous, hospitable stay you need, without hassle, headache, or unneccessary fees.

Book Your Stay

Testimonials

"Beautiful home. Love staying here so much that I have booked this place for my next 2 visits in Pensacola, and will also book this home in my future stays here in Pensacola."

Michelle

"My family and I thoroughly enjoyed our stay! The home was beautiful and spotless, with comfortable beds and a well,equipped kitchen. We especially loved the cozy patio area, it was perfect for relaxing. The outdoor shower was such a great touch after a day at the beach to remove the sand on us. Best of all, the beach and local shops were just steps away. Everything was perfect and exceeded our expectations!"

Jonathon

"⭐️⭐️⭐️⭐️⭐️ An Exceptional Stay – Immaculate and Stylish! I cannot say enough good things about this rental! From the moment we walked in, it was clear that cleanliness was a top priority—everything was spotless and fresh. The interior felt brand new, beautifully designed with thoughtful touches throughout. Every detail, from the comfortable furniture to the fully stocked kitchen and high-quality linens, was so well appointed. It truly felt like a luxury hotel with the comfort of home. Communication with the host was seamless, and check-in was a breeze. We would absolutely stay here again and highly recommend it to anyone looking for a top-tier experience!"

Jennifer

For Property Owners

Elevate your guest experience, attract more bookings, and streamline your maintenance with Elevated Escapes.

ELEVATE YOUR RENTAL