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Florida Keys Watersports

One of the best parts of the Florida Keys is that whether it's windy or flat calm, there's always a way to get out and enjoy the water. Otherside Boardsports offers lessons, rentals, tours, and charters 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 certified instructors, Otherside Boardsports is always ready to get you on the water! We offer various degrees of kiteboarding lessons and boat trips in Islamorada. We love windy days!

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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.


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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.

$$$$$ 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.

$$$$ The Islander Resort and Islander Bayside- Two great pools and an onsite restaurant/bar. Huge property and one of the biggest beaches in Islamorada (although artificial). Kiteable for advanced riders as there is a rock seawall. Deep water. ENE-S. 

 $$$ 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. ( 

$$$$$ Private Villa- Centrally located in downtown Islamorada. Walking distance from many restaurants and less than 2 miles from the shop. Brand new 4 bedroom, 3.5 bath. Sleeps 8. (

$$$$ Grassy Flats- Sustainable, kiteboarder-owned and operated resort on the Oceanfront in Grassy Key. 1.5 Miles from Keys Cable. Beach, pool and bar available to club members and guests. Kiteable on winds ENE-SW. Use discount code oTHErsidekite 

 $$$$$ 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