Islamorada Holidays

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Top Flight + Hotel Deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
President Hotel
Nobu Hotel Miami Beach
Park Central South Beach
EAST Miami
Hotel Riu Plaza Miami Beach

Where to stay in Islamorada

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

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.

Top hotels in Islamorada

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 €171 per night from 8 Oct to 9 Oct
€171
8 Oct - 9 Oct
includes taxes & fees
9/10 Wonderful! (1,211 reviews)
"Amazing!"

Reviewed on 2 Oct 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 €174 per night from 7 Oct to 8 Oct
€174
7 Oct - 8 Oct
includes taxes & fees
9.2/10 Wonderful! (1,531 reviews)
"Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect ..."

Reviewed on 4 Oct 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 €185 per night from 8 Oct to 9 Oct
€185
8 Oct - 9 Oct
includes taxes & fees
8.8/10 Excellent! (1,252 reviews)
"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."

Reviewed on 4 Oct 2025

Amara Cay Resort
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.

Popular places to visit

What to do in Islamorada

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