Our Jeeps

Jeep Gladiator for Rent in Key West

Are you ready for a Key West Adventure? Now, all you must do is choose which Jeep you want. We’ve got a wide selection of Jeeps to choose from. Whether you want a 2-door or 4-door, soft top, hard top, or no top at all, we’ve got the perfect Jeep to suit your style. Scroll through the photos of our Jeep fleet and pick the one you want. We also have Jeep Gladiators, minivans, Mini Cooper convertibles, slingshots, and basic cars available. All of our Jeeps are JL (2018 – current production) models with automatic transmission and air conditioning. Is rain in the forecast? No problem. Lightweight, easy-to-install covers are included in the event of an overnight drizzle. We will gladly install your Jeep’s top and doors in the event of a rainy day and take them back off when the sun comes out. Do you need beach chairs, umbrellas, and a cooler for your day trip? All are available in our lobby – we even provide ice! See more of the keys and be seen more in the keys with Key West Adventures!

If you need us in an emergency, send a text message to (708) 243-2208.


Jacked up Jeeps with lift kits, 35-inch tires, and customized to however we felt like creating. See and be seen. You’ll be liked, shared, and followed all over Instagram and Facebook when you post selfies taken in the Keys with a lifted Jeep. (click photo to enlarge)

JEEP GLADIATORS When we work hard and play hard love each other very much.

The Jeep Gladiator is 2020s North American Truck of the Year Award, and it could be your Key West cruiser. Doors can be removed from each Gladiator upon request.

The iconic Jeep Wrangler. Freedom on four wheels.

Pick your Jeep. Tops and doors can be off today and tomorrow.

Our goal is to make your vacation as fun and memorable as possible, only in a Jeep.

Most of our Jeeps are for sale. If you find the Jeep of your dreams, just ask. We’ll wrap it up, so you can take it home.

“Let’s go topless…” (click photo to enlarge)


You want the top down. You want easy to park. You want something snappy, something sporty. Here it is.

The Mini Roadster. The Mini Cooper Convertible

Roadsters seat two. Cooper's seat 4 Both have limited reasonable trunk space.

Need more room? Get a Jeep!

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For Mr. Dam, Mrs. Dam, and the whole Dam Family.

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Our Low-Cost Option is the Jeep Renegade, which is very popular in our family.

The Jeep Renegade is a very nice vehicle; it sets up to 5 and has great visibility.

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A vehicle designed for the Keys! Small enough to squeeze through the small keys streets with ease! Large enough to fit two tall adults comfortably! 

It's like a scooter with air conditioning!

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We have Slingshots for rent out of Key West.

A ride in a Polaris Slingshot on America’s Most Scenic Highway – US1 – Nothing else like it!

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