
Islamorada Vacations from ¥149,945
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The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Park Central South Beach
South Beach
Price was ¥249,214, price is now ¥150,839 per person
¥150,839
per person
Oct 3 - Oct 8
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
stayed here for our SB vacay super friendly staff lovely hotel everything is within walking distance the beach everything and the shrimp pasta omg the best!!! a must try
the next time i am in south beach this will be my first hotel
choice.
Reviewed on Aug 27, 2025


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

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 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

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥16,805 per night from Sep 1 to Sep 2
¥16,805
¥27,200 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,499 reviews)
"Fresh new rooms. Location was right on the ocean. Great breakfast, made for you. Front desk staff was amazing. Super accommodating and great communication. The only thing I would have recommended is that during construction they should have instated a bathroom vanity. Would return there again!!"
Reviewed on Aug 24, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥20,867 per night from Sep 4 to Sep 5
¥20,867
¥33,428 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (1,157 reviews)
"Excellent place for a restful weekend"
Reviewed on Aug 23, 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥24,753 per night from Sep 10 to Sep 11
¥24,753
¥37,622 total
Sep 10 - Sep 11
includes taxes & fees
8.8/10 Excellent! (1,240 reviews)
"Beautiful and the smell is wonderful"
Reviewed on Aug 25, 2025
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.
What to do in Islamorada

Original Snorkel and Sandbar Combo in Islamorada
¥22,049
per adult
90% of travellers recommend

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
¥38,280
per adult
100% of travellers recommend

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
¥36,802
per adult
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.