Free Shipping! Over $99* | Price Match Guarantee | Call Us! 305-853-9728

Florida Keys Watersports

One of the best parts of the Florida Keys is that whether it's windy or not, there's always a way to get out and enjoy the water. Otherside Boardsports offers lessons, rentals, tours, charters and cable sessions to ensure that no matter the conditions, we can help you have a great time. Check out the activities below to learn more about the Otherside experience.





With top notch riding conditions and an amazing team of PASA/IKO certified coaches, Otherside Boardsports is the number one kite school in the Keys to learn how to kiteboard or improve your skills. We offer various degrees of lessons and boat trips in Islamorada and Marathon to get you out on the water no matter what your riding ability.

Learn More



Stand Up Paddleboarding

Crystal clear water, abundant wildlife and flat-water riding conditions makes Florida Keys paddleboarding some of the best in the world. We offer paddleboard rentals and guided eco tours from multiple locations, including a waterfront location in Islamorada. 


Learn More



Wakeboarding and Cable Park

 Check out to learn more about our wake cable park located on Grassy Key. Fun for the whole family. 5-star Trip Advisor rated!


Learn More



Many of our traveling customers ask for recommendations on places to stay. Since everyone has different priorities, we've put together the following list to help you find something that is just right for your needs. As always, if you have additional questions or special needs, feel free to call the shop and we will try to help as best we can.

$$$$$ The Mooring Village- These boutique Island cottages sit on one of the only natural sandy beaches in Islamorada. Possibly the best (private) kite spot in town for riders beginner thru advanced. Accessible on wind directions from ENE-S

$$$$$ Cheeca Lodge- 5 Star resort with all the amenities. Restaurants, pools, spas and shops. Kiteable for advanced riders ENE-S.

$$$$$ The Caribbean Resort- No detail has been overlooked for these Caribbean-style homes. Choose from 1 bedroom-3 bedrooms and enjoy this secluded, tropically landscaped oceanfront getaway. Centrally located in Islamorada and walking distance to many great restaurants and shops. Managed by some of our favorite local Kiteboarders. Private kite beach is available to their guests.

 $$$$$ Casa Morada- Adult-only boutique hotel on the Bayfront. Great sunsets.

$$$$ Hawks Cay Resort- "The only Key you’ll need" is their motto since this high end resort offers every amenity and every activity you’ll want to do while here in the Florida Keys. Located between Islamorada and Marathon, it is only 1.5 miles from oTHErside’s Keys Cable Wakeboard Park, and is also the location of where our Marathon kiteboarding services are based.

$$$$ The Islander Resort and Islander Bayside- Rooms are basic but clean, well-kept and updated. Two great pools and an onsite restaurant/bar. Huge property and one of the biggest beaches in Islamorada (although artificial). Kiteable for advanced riders ENE-S.

 $$$$ The PostCard Inn- Newly renovated, this hip property is home base for Otherside’s Islamorada Based kiteboarding services. This would be a super convenient stay if you’re planning on kiting with us. The property also has a handful of bars, restaurants, watersports and other activities.

 $$$ Pines and Palms Resort-Best Value! One of our favorite properties in the area, this locally run resort offers beautifully kept grounds and lodging options that range from motel-style rooms to multi-bedroom flats. Oceanfront with pool. Kitable for advanced riders ENE-S.

 $$ Sunset Inn- Basic and clean, this motel is centrally based in Islamorada. Non-waterfront

 $$ Key Lantern Inn- When you’re spending all day on the water and a clean place to sleep is you’re primary goal, this is your ticket. With small kitchens in each room, this is the best option for budget-minded travelers. Non-waterfront

 ($) Tent Camping- Check out our great state parks! Long Key, Curry Hammock and Bahia Honda all have oceanfront, kiteable tent sites. (