Islamorada Vacations from ￥285,726
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The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel
South Beach
Price was ￥412,903, price is now ￥285,726 per person
￥285,726
per person
Dec 1 - Dec 6
found 2 hours ago
Roundtrip flight included
Osaka (OSA) to Miami (MIA)
8.2/10 Very Good! (1,440 reviews)
It was across the beach and near Starbucks and other places that we want to visit like Versace mansion. Everyone were friendly especially Carmen at the front desk. Carmen was helpful
Reviewed on Oct 9, 2025
Bentley Hotel South Beach
South Beach
Price was ￥523,513, price is now ￥339,654 per person
￥339,654
per person
Dec 1 - Dec 6
found 2 hours ago
Roundtrip flight included
Osaka (OSA) to Miami (MIA)
9.2/10 Wonderful! (334 reviews)
Location is amazing, room confort and facilities really good. Staff very friendly and helpfull. I had an amazing experience.
Reviewed on Oct 9, 2025
President Hotel
South Beach
Price was ￥433,298, price is now ￥294,010 per person
￥294,010
per person
Dec 1 - Dec 6
found 2 hours ago
Roundtrip flight included
Osaka (OSA) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
Me gustó bastante la habitación con balcón, cómoda, amplia y con un baño grande...
Reviewed on Oct 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 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, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ￥21,015 per night from Oct 15 to Oct 16
￥21,015
￥33,848 total
Oct 15 - Oct 16
includes taxes & fees
9/10 Wonderful! (1,220 reviews)
"room were cleaned every morning; we were able to park under the room drinks were pricy"
Reviewed on Oct 9, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ￥22,153 per night from Oct 19 to Oct 20
￥22,153
￥33,426 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (1,532 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 Oct 4, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ￥19,497 per night from Oct 14 to Oct 15
￥19,497
￥31,970 total
Oct 14 - Oct 15
includes taxes & fees
8.8/10 Excellent! (1,253 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 Oct 4, 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
￥9,814
per adult
96% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
￥6,885
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
￥9,521
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.
