
Islamorada Vacations from ¥176,444
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 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
The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.




Fontainebleau Miami Beach
Mid Beach
per person
Oct 7 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (6,713 reviews)
Beautiful property.
One major downfall of this property is with it being as luxurious as it is there was nothing open or anything available to early risers for coffee enjoyment. Ive been to numerous hotels and there is ALWAYS coffee available pre-breakfast downstairs.
The bed is extremely comfortable. I wish i knew the model of the bed and pillows i slept on to oreder for my home.
The rooms are set up perfectly.
Disappointed they dont offer Hotel Shuttle to and from the airport for there guest. Disappointing they rather have there guests book an expensive private ride which for one person is over a hundred dollars or prearrange other transportation. This is disappointing.
The food. The food is out od this world expensive. Lets not talk about the water. The only bottled water which is offered is Fiji, big bottle $12.80, smaller bottle around $8. If you are ordering food inside the restaurant they will provide a take out cup of water.
The gym is located far from where you stay. It is clean and opens at 6am which if we stay in the hotel it should be keyroom accessed 24/7 not limited.
With the amount of money we are paying for our stay, im Disappointed that we are limited on simple access to the basics.
The facility is super clean. Staff is very nice.
Reviewed on Aug 13, 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 ¥19,796 per night from Aug 24 to Aug 25
¥19,796
¥30,553 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (1,497 reviews)
"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"
Reviewed on Aug 11, 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥22,712 per night from Aug 17 to Aug 18
¥22,712
¥35,491 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,146 reviews)
"Golf course could use just a little work. Everything else was great."
Reviewed on Aug 12, 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥24,749 per night from Sep 1 to Sep 2
¥24,749
¥37,616 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,239 reviews)
"The staff was very personable and accommodating.. it was our 32nd weeding anniversary and they had left a handwritten note and a treat in our room… it was appreciated… The grounds were nice and clean with the exception of the water area around the end of the property where the event area is located ..."
Reviewed on Aug 11, 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
¥22,032
per adult
90% of travellers recommend

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
¥36,775
per adult

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
¥38,252
per adult
100% of travellers recommend
Frequently asked questions
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.