Islamorada Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Islamorada showing a beach bar

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

Find the Best Islamorada Vacation Packages

Islamorada Beach Vacation

Relax along the shoreline and feel the wind through your hair during your Islamorada vacation. 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 kilometers from the town center. 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 vacation homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbor 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.

Islamorada Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩287,004 per night from Nov 20 to Nov 21
₩287,004
₩420,238 total
Nov 20 - Nov 21
includes taxes & fees
9/10 Wonderful! (1,265 reviews)
Always a great stay at Cheeca. Lovely property, great restaurants, clean rooms and wonderful service by the staff.

Reviewed on Oct 30, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩272,654 per night from Nov 12 to Nov 13
₩272,654
₩387,859 total
Nov 12 - Nov 13
includes taxes & fees
9.2/10 Wonderful! (1,552 reviews)
Friendly staff

Reviewed on Nov 2, 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩222,933 per night from Nov 30 to Dec 1
₩222,933
₩346,534 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (1,277 reviews)
Great stay except for the fact that we could not watch the World Series in the comfort of our room!! Really? Other than that thoughtless error our stay was relaxing and fun.

Reviewed on Nov 3, 2025

Amara Cay Resort
See all 2,226 properties in Islamorada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Islamorada

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Sunset Drive Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.