Islamorada Vacations from ￥430,963
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Henrosa Hotel
South Beach
Save 100% on your flight
Price was ￥831,016, price is now ￥485,478 per person
￥485,478
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.4/10 Very Good! (829 reviews)
Rooms were clean and the staff were good as well.
Reviewed on Nov 19, 2025
Bentley Hotel South Beach
South Beach
Save 100% on your flight
Price was ￥972,099, price is now ￥598,703 per person
￥598,703
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.2/10 Wonderful! (466 reviews)
Everything was gorgeous and extremely comfortable!
Check in was smooth and friendly! Thank you!
Reviewed on Nov 26, 2025
Flow Miami Hotel
Downtown Miami
Price was ￥665,440, price is now ￥435,412 per person
￥435,412
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.2/10 Wonderful! (172 reviews)
The amenities were great. The balcony and the balcony view made every penny worth it - on top of that, the fully stocked kitchen and super comfy living space were relaxing. It would be cool if there was a tv in the bedroom, though…
Reviewed on Nov 9, 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 Florida Keys Brewing Co. 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 ￥19,369 per night from Dec 7 to Dec 8
￥19,369
￥30,578 total
Dec 7 - Dec 8
includes taxes & fees
9.2/10 Wonderful! (1,585 reviews)
Room was very clean, view was amazing, breakfast was great, and restaurants and activities nearby. Only issue was hot tub not working. Would’ve enjoyed that amenity!
Reviewed on Nov 24, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥32,444 per night from Dec 15 to Dec 16
￥32,444
￥47,045 total
Dec 15 - Dec 16
includes taxes & fees
9/10 Wonderful! (1,275 reviews)
This was a great property. Numerous dining options. I was so impressed with the grouper sandwich, possibly the best that I’ve eaten in 30 years in Florida and the Florida Keys. The customer service staff was amazing and so thorough informing guest at check-in of all of the amenities available to ...
Reviewed on Nov 23, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥21,978 per night from Nov 30 to Dec 1
￥21,978
￥35,095 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (1,269 reviews)
Loved the resort
Reviewed on Nov 21, 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
Mangroves and Manatees - Guided Kayak Eco Tour
￥10,546
per adult
96% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
￥7,398
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
￥9,923
per adult
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.
