Vacation Rentals in the Florida Keys: Your Gateway to Island Living

Pinnacle Choice Properties offers a carefully selected collection of vacation rentals throughout the Upper Florida Keys, including Key Largo, Tavernier, and Islamorada. Known for personal service and local expertise, the company focuses on making every stay comfortable, clean, and memorable. Guests enjoy easy direct booking, responsive communication, and properties that reflect the relaxed charm and natural beauty of the Florida Keys.

Why Book With Us?

Local knowledge makes all the difference when booking your Florida Keys getaway. Pinnacle Choice Properties offers direct communication with a team that knows the area inside and out, ensuring personalized recommendations and smooth planning. Booking through us means no hidden platform fees, premium care of every property, and the confidence that your vacation rental is clean, comfortable, and ready for your arrival.

Local experts, real insights.

No hidden fees—ever.

Direct, personal service.

Clean, cared-for homes.

Stress-free planning.

Trusted, transparent bookings.

Explore the Florida Keys

Discover the natural beauty and laid-back lifestyle of the Upper Florida Keys. From snorkeling and fishing in Key Largo to enjoying waterfront dining in Islamorada or relaxing in Tavernier’s peaceful surroundings, the options are endless. Our vacation rentals provide the perfect home base to explore all the Keys have to offer while coming back to a private, well-maintained retreat.

Discover the True Magic of the Keys with Local Insight

To fully experience the Florida Keys, you need a local’s perspective. Staying in one of our exceptional Florida Keys vacation rentals means gaining insider access to the best dining spots, hidden gems, and authentic activities loved by residents—details you won’t find in any guidebook. Explore our curated properties and book your stay today to unlock your personal island paradise.

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Hear From Our Guests

Nothing speaks louder than the experiences of those who have stayed in our Florida Keys vacation rentals. Our guests consistently praise the comfort, cleanliness, and personalized service that make each stay memorable. Read their stories to discover how Pinnacle Choice Properties helped create unforgettable island getaways filled with relaxation, adventure, and authentic local charm.

"Everything you need in one place and easy access to all the Keys have to offer."

Katherine L.

"It is really clean and well stocked. A great place to spend all your time or use as a home base to explore the Keys and Everglades."

Paula V.

"This was a great place to stay with a great view of a tranquil mangrove shoreline. The condo was clean and it was exactly as advertised. We would stay there again."

Cindy J.