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Boat 
Rental

Charters

Accomo-
dations

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Golf Cart
Rental

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Unlock the ultimate island escape with Annie, your go-to Florida Keys vacation concierge! Seamlessly swap your car keys for a breezy golf cart rental, settle into your dream waterfront vacation home, and hit the crystal-clear waters on a premium boat rental. 

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Whether you want to anchor down on a vibrant sandbar charter or uncover hidden local gems, Annie handles all the details so you can simply soak up the sun. Your perfect tropical adventure starts here—worry-free and completely customized for you.

About Annie

For over 14 years, I’ve called the Florida Keys home while owning and operating Backcountry Boat Rentals. Over that time, I’ve gotten to know the Keys from the water up — the best places to explore, the local businesses worth knowing, and the people who make this community special.

 

Annie’s List — Your Local Keys Connection is a natural next chapter for me. I’m using my years of local experience, knowledge, and personal connections to help you discover the Keys the way a local would.

 

Whether you’re looking for a boat, a fishing trip, a great place to stay, a sunset cruise, or a hidden gem, I’m here to point you in the right direction.

 

14 years of local experience. Real Keys connections. One trusted source — Annie.

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Key Largo, Islamorada & The Upper Keys

Explore the Upper Keys at your own pace. From hidden sandbars to hidden coral reefs, your ultimate Florida Keys adventure starts at the helm of your own private rental 

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Middle Keys

Welcome to Marathon and the Middle Keys-the sweet spot of the Florida Keys where open water adventures are right at your fingertips.

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Lower Keys

Boating in the Lower Keys offers a pristine, laid-back escape where you can cruise from the protected backcountry of Big Pine Key all the way down to the vibrant, historic shores of Key West.

Reviews

Rent a double decker pontoon with slides and spend the day at beautiful Marvin Key. This is the highlight of our annual Keys trip! Annie and her staff are amazing and so are her boats! Top notch service at reasonable rates! She is very knowledgeable and always takes great care of our large group!

J. McClosky

Feb. 2026

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Renting a small pontoon boat for a day of swimming and sunning was one of the highlights of our trip to the Keys. The process was smooth and easy and Jenn did a perfect job of teaching us all we needed to know. We hung out at Marvin Key and it was beautiful. We saw lots of sea birds and fish. Even a shark swam by us while we relaxed in the shallow water near the sandbar. Highly recommend using this company!!

A. Woodring

3 months ago

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We have rented from Backcountry Boat Rentals for many years for our annual Valentines Day Boat trip to Marvin's Key out of Sugarloaf Marina. We rent 2 of the their double decker boats with slides and spend the day with our friends and family sitting on the sandbar, swimming, eating, floating, fishing and exploring. It is the highlight of our annual Keys trip.

J.McClosky

6 months ago

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