Tour and Rental Activities in
Islamorada, Florida Keys

Posted July 18, 2018

Blue, blue, and more blue! The Florida Keys is the United States tropical paradise. Islamorada, one of the first Florida Keys, offers many ocean-side diversions. We can't get tired of all the vibrant colors of blue that are right outside our window.

Ok, sure - Key West is known for its beach and touristy stuff, but did you know that there are quite a few gorgeous getaways on some of the other Florida Keys like Islamorada? We'll get to all of those excursions in a bit, but, before we do, we encourage you to book your rentals TODAY to avoid major disappointment.
Before you reserve a rental in Islamorada, Florida, make sure to read the reviews and check out the pricing differences for each company you are considering. wants you to make the most of your trip by knowing all your options.

A1A Watersports and Boat Rentals

If freedom riding is what you're after, A1A Watersports & Boat Rentals has the largest open water riding area around. Their fleet of waverunners always includes some of the newest Yamahas jet skis available. Each waverunner provides a stable and comfortable ride for 1 to 3 passengers. Whether you feel the need for speed or just want a slow steady ride, A1A Watersports & Boat Rentals has the right jet ski for you.
A personal flotation device and full safety instructions are provided so beginners and young riders will feel confident.

Florida Keys Watersports

Have you ever been on a jet ski tour? Florida Keys Watersports goes by the homes of the rich and the famous on Venetian Shores where you can see the stars live.
Florida Key Watersports wants you to know that they are different that your regular jet ski rental in Islamorada. Instead of giving you a square that you have to stay in, Florida Keys Watersports lets you explore a better side of Islamorada by taking you to places that only the locals know about.

All in Watersports

Experience the thrill of riding the beautiful waters of the Florida Keys on All In Watersport's waverunners. All In Watersports offers you the best jet ski rentals in Islamorada with a variety to choose from. You won’t find a more exciting and memorable family activity for your vacation. Their team will walk you through how to ride and give you full safety instructions.
All In Watersports also provide all riders with appropriate life vests. Book your jet ski experience today and make ever lasting memories!

Islamorada Watersports

Experience over 25 miles of Islamorada, through mangrove tunnels and across reefs. Stop to snorkel, feed tarpon, and fill your need for speed through the open water.
See marine life and all the islands you simply cannot experience from land. The private guided tour lasts about two hours and includes fuel and snorkel equipment.

Kayak Shack

Explore the beautiful bays basins & mangrove tunnels in Islamorada with our 14-22 mile tour! Get out and ride with Kayak Shack's jetski tours. Discover the beautiful turquoise waters all around Islamorada and experience dolphins and manatees playing in their natural habitats.
Enjoy “The Best Part of Your Vacation” right here with the Kayak Shack. Located near the infamous Robbie's Marina.

Paddle the Florida Keys

Paddle or ride with Paddle the Florida Keys for the day — launch out their back door right into the water. Paddle the Florida Keys also brings the fun to you, and lets you keep the rentals overnight or for your entire vacation. Paddle the Florida Keys offers low daily rates with discounts for additional days, as well as weekly and monthly prices.

Aquaholic Adventures

Aquaholic Adventures specializes in premium eco-tours day or night. That's right - night tours which look pretty sweet! They have the best mangrove tunnel tours in all of the Florida Keys! Sign up for premium guided mangrove tunnel day or night tours. Aquaholic has several launch sites throughout the keys, however one of their most popular is Post Card Inn at mile marker 84.
Typically, it takes Aquaholic about 10 to 15 minutes to get most first time people standing up and paddling! After you feel comfortable, you can explore the area and enjoy your time!

Beach Bum Paddlesports

Beach Bum Paddle Sports is your best source for paddle board rentals, paddle lessons, and eco tours in Islamorada, Florida Keys. Take advantage of their free home delivery service for daily and weekly rentals of paddleboards.

What makes Beach Bum Paddlesports different? World class customer service gives our customers the safest, most comfortable and memorable paddling experience on the beautiful waters of the Upper Keys.

Islamorada Paddle

Explore more of Islamorada on Islamorada Paddle's exclusive boat assisted stand up paddleboard tours. Enjoy a scenic boat ride aboard their 28ft catamaran on the way to your destination and experience. Islamorada Paddle offers stand-up paddleboarding, swimming, and snorkeling around Islamorada in a completely different way.
Check out their eco-tour and sunset paddling tours!

Aquaholic Adventures

Aquaholic Adventures delivers kayaks anywhere in Key Largo or Islamorada. You can paddle for a few hours or keep them up to 24 all for the same price. Renting a vacation house for the week? Aquaholic Adventures can have boards or kayaks waiting for you when you arrive! All delivery and pick up is free.
Need snorkel gear? No problem. Aquaholic Adventures has all fin sizes from child to adult. They know all the best locations to go and aren’t limited to leaving from just one spot.

Back Country Cowboy

Guided kayak nature tours, kayak rentals or Sunset Kayaking. All great individual or family adventures.
Backcountry cowboy will be glad to assist you, your family or your group in getting the most out of your trip to the beautiful Florida Keys. Our retail store is located on Islamorada on US 1 at mile marker 82.2.

The Kayak Shack

The Kayak Shack offers the best kayaking in the Florida Keys. They are nestled in a tropical place known as Robbie’s Marina. Explore two state parks – Indian Key & Lignumvitae Key. Plus, observe mangrove eco-systems, island exploration, and snorkeling in the turquoise waters of Islamorada.
The Kayak Shack love first timers! Everyone receives pre-launch instruction on safety, the equipment and the environment.

Backcountry Cowboy

Islamorada bike rentals are a breeze at Backcountry Cowboy Outfitters. Backcountry Cowboy offers well maintained bike rentals for your enjoyment and exercise. They offer speed cruisers, speed townie's, speed hybrid/fitness bikes and road bicycles. Explore the islands in style and comfort. Bike rentals in the Florida Keys are the best way to see the islands!

Islamorada offers some of the most bike-friendly areas and scenic pathways in the Florida Keys. After even a short adventure by bike, you'll gladly leave your vehicle where you're staying to explore the Upper Keys by bike.

A1A Watersports and Boat Rentals

A1A Watersports has quite a fleet of rental boats include fully equipped center console, deck boats and pontoons​ ranging from 16-27 feet. Whether you're looking to fish, snorkel, sightsee or head to the party on the Sand Bar, A1A's knowledgeable and friendly staff will work with you to customize a self-guided tour sending you directly to the best locations.

A1A Watersports offers half-day, full day, multi-day, weekly and monthly boat rentals. Chart and instructions provided. Fishing and snorkeling gear available for rental. Plus, enjoy free use of their beach, BBQ's, Water Front TV's and party on the "Famous Islamorada " Sandbar.

Bayside Boat Rentals

Whether you're a first time visitor or an original "conch", Bayside Boat Rentals offers the experience, local knowledge, and the perfect boat for you! Plus, Bayside Boat Rentals also delivers your boat.
Bayside Boat rentals have vary nice fishing boats, and all of our fishing boats come fully equiped with color gps/depth sounder, stereo, and some good fishing spots. Every one of their boats are clean and in perfect working order.

Bump & Jump Boat Rentals

Bump & Jump boat rentals offers boat rentals in the Florida Keys – located in Islamorada with delivery from Key Largo to Key West. Bump & Jump Boat Rentals can help you enjoy the beautiful waters of the Florida Keys whether your main activity is fishing, diving, or snorkeling!
Bump & Jump have over 30 years of boating, sailing, windsurfing, fishing, and diving experience in Islamorada and the upper Keys. They know how to meet all your boat rental needs.

Holiday Isle Boat Rental

Holiday Isle Boat Rentals offers the most complete experience while you stay in Islamorada. Best local pricing for your boat rental needs. Holiday Isle services all your vacation needs in one spot.
Center console boats will most likely be your best value. They're the most widely used in the Keys, and tend to be safer and easier to operate. Great for fishing, diving, pleasure cruising around Islamorada and visiting Islamorada's world-famous sandbar! The boats are fueled and ready for your arrival.

Islamorada Watersports

For over 15 years, the Islamorada Watersports Company has been serving locals and visitors to the Florida Keys with all kinds of fun out on the water. They specialize in making your vacation experience unforgettable, easy and fun!  Islamorada Watersports operates in Islamorada from Whale Harbor Marina and Bud N Mary's Marina on the north and south end of Upper Matecumbe Key. They can deliver and are happy to ride along to help show you the beautiful area.

No matter which company you choose, you are bound to have a crazy amount of fun enjoying the Florida sun and crystal-clear water. All of these rental companies are reputable, have great reviews, and happy customers.

It simply boils down to which business is more convenient, which excursion you prefer, and what price point you want are willing to pay. For you, the dilemma is simply choosing!

Plus, if we're missing a company on this article please feel free to reach out via Facebook or Twitter!

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