Islamorada Vacations from ￥347,906
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The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Price was ￥483,567, price is now ￥347,906 per person
￥347,906
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back
Reviewed on Feb 24, 2026
Hotel Riu Plaza Miami Beach
Mid Beach
Price was ￥596,394, price is now ￥405,922 per person
￥405,922
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.
Reviewed on Feb 19, 2026
The Penguin Hotel
South Beach
Price was ￥486,183, price is now ￥353,314 per person
￥353,314
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
It was perfect. It was right across from the beach lots of shops lots of restaurants lovely area.
Reviewed on Feb 24, 2026
President Hotel
South Beach
Price was ￥484,422, price is now ￥352,580 per person
￥352,580
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Staff was very friendly and great locations. The rooms were decent for the price but did have a mild funky aroma. I guess that can expected when you are in such a humid hot environment..
Reviewed on Feb 24, 2026
Bentley Hotel South Beach
South Beach
Price was ￥591,052, price is now ￥441,946 per person
￥441,946
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (466 reviews)
Great place to stay. Clean spacious room in a nice location.
Reviewed on Feb 26, 2026
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
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥95,903 per night from Feb 27 to Feb 28
￥95,903
￥119,293 total
Feb 27 - Feb 28
includes taxes & fees
9.2/10 Wonderful! (1,297 reviews)
This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.
Reviewed on Feb 25, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥47,393 per night from Mar 1 to Mar 2
￥47,393
￥62,099 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (1,654 reviews)
Nice clean spacious room.Beautiful location overlooking the water.Staff was eager to please
Reviewed on Feb 24, 2026
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥68,882 per night from Mar 22 to Mar 23
￥68,882
￥87,857 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (157 reviews)
All was fantastic. Very nice staff. Clean room. Highly recommended
Reviewed on Feb 23, 2026
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
￥10,680
per adult
96% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
￥7,584
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
￥10,370
per adult
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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.
