Pinnacle Choice Properties

Your Keys, Made Easy

Meet Pinnacle Choice Properties, your locally owned guide to island living across Upper Florida Keys.

About Us

Pinnacle Choice Properties began as a small, locally rooted business with a deep love for the Florida Keys, and has grown into a trusted name in island vacation rentals. We are independently owned and personally invested in every stay, which means real people who know these islands, not a corporate call center. Our curated collection of homes is chosen for comfort, character, and that laid-back luxury feel, then cared for to the highest standard. From your first search to your final sunset, we make direct booking simple, personal, and rewarding, so you get the best value and a true local welcome.

Living the Island Life

Home for us is the Upper Florida Keys, and we know every mile marker by heart. Our homes are spread across Key Largo, Tavernier, and Islamorada, from waterfront retreats with private docks to easygoing island hideaways, many of them pet friendly. Because we live and work here, we do more than hand you the keys. We point you to the best snorkeling spots, the freshest seafood, the quiet sandbars, and the local gems you would never find online. Whether you are chasing adventure or slowing down to island time, Pinnacle Choice Properties is your home base for the real Florida Keys.

Locations

Our Bases Across the Keys

Tavernier

The Quiet Middle

Tavernier

A peaceful, tucked-away corner of the Upper Keys with a true local feel.

Islamorada

The Village of Islands

Islamorada

The sportfishing capital of the world, famous for waterfront dining and sandbar afternoons.

What We Offer

Three Ways We Help

Curated Rentals

Curated Rentals

Each home is carefully maintained and thoughtfully designed for comfort and style.

  • Ocean views and private docks

  • Pet-friendly options available

  • Cleaned to highest standards

Direct Booking

Direct Booking

Book with us and skip the platform fees. You get the lowest rate and personal support.

  • No hidden fees or markups

  • Faster answers and smoother communication

  • Better rates than third-party sites

Local Knowledge

Local Knowledge

Our team lives in the Keys and can guide you to the right rental and the best experiences.

  • Know the neighborhoods and culture

  • Help you find your ideal escape

  • Available by phone or email