Kayla Simons is a dedicated travel agent with Pineapple Escapes, bringing four years of experience in crafting unforgettable vacations. She has been married to her high school sweetheart for 14 years, and together they have three boys—Zeke (10), Jack (8), and Wes (5). Their family also includes an AussieDoodle named Darth “Vader” and a cat named Stitch—clear signs they are a true “Disney” family! They love visiting Disney destinations, including Walt Disney World, Disneyland, and sailing with Disney Cruise Line. When they're not enjoying the magic of Disney, they also love cruising with Royal Caribbean and relaxing on sun-soaked beaches. For them, the perfect vacation means warm sunshine and water.
Kayla’s goal is to make the vacation planning process simple and enjoyable while designing the best travel experiences for her clients. She specializes in family and friends’ vacations, as well as romance travel for honeymoons and anniversaries. Her expertise includes custom vacation packages to Disney and Universal destinations, all-inclusive Caribbean resorts, and cruises with Royal Caribbean, Disney Cruise Line, and Virgin Voyages. Beyond resort and cruise bookings, she assists with excursions, travel insurance, and flights—ensuring a seamless and stress-free travel experience.
Whether you're dreaming of a magical family getaway, a romantic escape, or a fun-filled cruise adventure, Kayla is ready to turn your vacation dreams into reality!
niche: Disney/Universal Destinations, all-inclusive Caribbean getaways, cruises (Royal Caribbean, Disney Cruise Line, Virgin Voyages)
Kayla Simons
agent bio
Kayla Simons
wendy smiley
Kayla helped us book our first Disney vacation and everything went very smooth! The process is very overwhelming but Kayla patiently answered so many questions I had, and shared all her Disney tips and tricks. She even had a final itinerary for us to follow which was so helpful. We would highly recommend her to anyone planning a vacation! Thank you for making our first Disney vacation memorable! We can't wait to work with you again in the future!
"her bubbly & helpful personality put us at ease with the planning."
katie hughes
After many fails with local travel agents, someone recommended Kayla. She was very knowledgeable and if she didn't have an answer right away, she would find one. We traveled with a group and she made sure we were all well taken care of. Will definitely only use her in the future and will recommend her to everyone.
"she was a god send. she listened and gave us exactly what we wanted."
beth weberski
She made booking a breeze and had so many helpful tips and tricks. She checked in on us while we were there to make sure everything was going smoothly. Even on our departure day was quick to respond and help us change our transportation when our flight kept getting delayed. Would highly recommend using Kayla for Disney and other trips for a travel agent, I know we will!
"kayla helped make our first disney trip a huge success!"
Booked our first trip to Mexico with Kayla and I was so NERVOUS. She answered all my crazy questions and reassured me everything was fine! She goes out of her way to make sure you're okay, if you made it home! She's literally the BEST. Will be using her again in the future for our trips and recommending her to everyone!
"the best decision! she was there every step of the way."
