Kayla D'Ascanio, Realtor

11/19/2025

I have shifted my focus from real estate to my creative business, Pineapple Smiles Graphics. If you would like to follow along with my design work, custom gifts, and social media projects, I would love to see you there.

You can follow me at for all the fun new things I am creating.

Big update for me and my creative world. After years of running Pineapple Smiles Graphics on the side, I have officially paused my real estate license so I can focus on this business full time.

Creativity has always been where I feel most at home. Designing for small businesses, crafting personalized gifts, creating event decor, and supporting others with their social media and marketing has become something I truly love.

My time in real estate taught me the power of strong visuals, storytelling, and thoughtful marketing. I am excited to bring that experience into this next chapter and continue helping agents and small businesses stand out online.

Thank you to everyone who has supported this passion over the years. I am so excited to grow, create, and share so much more.

https://pineapplesmiles.com/

07/03/2025

Living here means the days don’t end when the sun goes down — that’s when the Keys magic really begins. ✨🌊🏡If you’re here for the holiday and dreaming of making this lifestyle your own, we’d love to show you what’s possible — by land or by sea.Why not explore the homes that could make this lifestyle your everyday? ✨

05/04/2025

This May the 4th, we’re celebrating homes that are truly out of this world. Whether your dream escape is a modern coastal retreat or a Keys estate fit for a Jedi Master, let us be your guide to the galaxy’s most exclusive destinations. ⭐️💫821 W Ocean Drive #3, Key Colony BeachMLS # 609403 | Offered at $1,895,000

04/22/2025

This Earth Day, we’re reminded of the natural luxury all around us. 🌎Swaying palms, ocean breezes, and the sound of birdsong—there’s no place like the Florida Keys. Protecting paradise is part of living in it. Love where you live. Live where you love.

04/17/2025

Where serenity meets the shore—this is life in the Florida Keys. Discover this oceanfront escape. Did you miss out on our open house today? No problem, schedule your private showing with us to find if this slice of paradise is right for you. ☀️

04/15/2025

Join the Marathon agents of Ocean Sotheby’s International Realty for a special morning tour featuring multiple properties throughout Key Colony Beach.

04/10/2025

Whether you’re relocating or investing, you’re not just buying a home—you’re buying the lifestyle. This is more than a destination—it’s a way of life. 🌴Looking to make the Keys your home (or home-away-from-home)? Let’s talk.

02/12/2025

It's not too late to get your love what they really want this Valentine's Day. ❤️ Design and Build by D'Asign Source

02/11/2025

🏠 Is it the right time to stop renting and start investing? Your local agent like myself can make this process go a little more smoothly if you come into this process asking these items first. So let’s see if this next life journey is right for you!

01/24/2025

Join one of our agents this weekend and find your family’s dream home! Unfortunately the baby is not included in any home. Can’t make one this weekend? Reach out to me and let’s find a good time for you to view them!