
Islamorada Vacations from ¥188,595
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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
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
A Perfect Stay on Ocean Drive
I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!
Reviewed on Jul 31, 2025


The Gabriel Miami South Beach, Curio Collection by Hilton
South Beach
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!
Reviewed on Jul 31, 2025

Kimpton EPIC Hotel by IHG
Downtown Miami
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
The bed was divine. I love king size beds. The room had accessibility bars for me to get me back up.
Free flavored water for those interested.
Reviewed on Jul 30, 2025

Fontainebleau Miami Beach
Mid Beach
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
The property is very large. The tower our room was located in had severe problems with elevators not working throughout the entire stay making it difficult going up and down from room. Pool services were not great and on many days we had to find the towels and prepare our chairs ourselves. The cleanliness around the pool also was not kept up.
The room was very large and comfortable and spacious and the staff in our tower were nice.
We had a pleasant stay though I am not sure I would stay here on a future visit.
Reviewed on Jul 31, 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

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥25,261 per night from Aug 14 to Aug 15
¥25,261
¥38,499 total
Aug 14 - Aug 15
includes taxes & fees
9/10 Wonderful! (1,145 reviews)
"So this is my first time visiting Cheeca Lodge- I have alway"
Reviewed on Jul 28, 2025

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥19,852 per night from Aug 10 to Aug 11
¥19,852
¥30,735 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,494 reviews)
"The hotel is wonderful"
Reviewed on Jul 28, 2025

Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ¥30,884 per night from Aug 12 to Aug 13
¥30,884
¥44,766 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (1,028 reviews)
"Amazing resort and staff. Felt like I was on a tropical island and in a whole other world. Food was amazing! Rooms were beautiful and beds were super comfortable. Would definitely be coming back!"
Reviewed on Jul 28, 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
¥21,868
per adult
90% of travellers recommend

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
¥36,501
per adult

1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
¥37,967
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.