Islamorada Holidays
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Our guide on where to stay in Islamorada
Matecumbe
If you're spending some time in Matecumbe, Robbie’s of Islamorada and Anne's Beach are top sights worth seeing.
Islamorada Holiday
Islamorada Beach Holiday
Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometres from the town centre. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.
Things You Should Know About Islamorada
- Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
- If you're searching for lots of room to spread out and relax, Islamorada private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour and Bud N' Mary's Fishing Marina will fit the bill.
- Roughly 7 100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.
Our pick of the best Islamorada Hotel Deals
Cheeca Lodge & Spa
"All good !!!!!!!!!!!!!!!"
Reviewed on 8 June 2026
Chesapeake Beach Resort
"A beautiful place to stay on the Florida Keys! The staff were all so nice, breakfast was good, and the views were unbeatable. We would definitely consider returning!"
Reviewed on 7 June 2026
Islander Resort
"Great place to stay will come back again has many amenities that other resorts change extra for"
Reviewed on 8 June 2026
Discover the most popular places to visit in Islamorada
Anne's Beach
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Windley Key Fossil Reef Geological State Park
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
History of Diving Museum
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
What to do in Islamorada
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Islamorada Sunset Cruise with Champagne Toast and Snacks
