Islamorada Vacations from ￥369,466
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The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sense28 Edgewater, an AvantStay Hotel
Midtown
Price was ￥463,780, price is now ￥369,466 per person
￥369,466
per person
Jun 24 - Jun 28
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
10/10 Exceptional! (14 reviews)
Great location for downtown - apartment was well organized for a family stay and the staff helpful
Reviewed on Apr 10, 2026
Bentley Hotel South Beach
South Beach
Price was ￥590,038, price is now ￥420,727 per person
￥420,727
per person
Jun 24 - Jun 28
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.4/10 Exceptional! (745 reviews)
The Bentley hotel was a really nicely appointed place to stay in South Beach Miami. The staff was very welcoming, friendly and always available to assist. We used the bikes we had Prosecco on the rooftop and anytime we had a request the staff responded to things promptly. I would go back again and stay at this property in a heartbeat. So lovely!
Thank you!
Reviewed on Apr 12, 2026
Flow Hotel Miami
Downtown Miami
Price was ￥483,780, price is now ￥393,460 per person
￥393,460
per person
Jun 24 - Jun 27
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9/10 Wonderful! (256 reviews)
We stayed over the Easter Weekend. The room/space was alot bigger than we expected. It was very well equipped and comfortable.
We had an excellent and easy check in experience.
The hotel's location is very good if you want to explore the downtown and plan to go to the Kayesa center.
We would have liked to use the spa and exercise space, however we ran out of time.
The shower curtain had the smell of dampness that lasted too long.
Otherwise, we enjoyed the stay and would uss this Flow location again.
Reviewed on Apr 8, 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 Robbie’s of Islamorada 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 ￥40,479 per night from May 3 to May 4
￥40,479
￥57,186 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,315 reviews)
The rooms we were in were definitely tired with thin walls. You could hear everything in the room next door. The golf course lodging probably needs to be torn down and rebuilt. The property/location was great and the staff were super friendly.
Reviewed on Apr 12, 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥29,491 per night from May 7 to May 8
￥29,491
￥42,137 total
May 7 - May 8
includes taxes & fees
9.2/10 Wonderful! (1,697 reviews)
We loved this property and highly recommend it. Jonathan at the front desk is smart and professional. He set the tone for our amazing stay. The breakfast is the best of any hotel on our trip through all the keys. Most importantly, there is a peacefulness about this property that puts you at ease. ...
Reviewed on Apr 11, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥45,524 per night from Apr 20 to Apr 21
￥45,524
￥62,862 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,275 reviews)
Great location. Eat at Lazy Days next door and Flagler Station if you want more upscale. They have a water taxi that unfortunately we didn’t get to go on because it was so windy but hope to go again and get on it next time.
Reviewed on Apr 12, 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
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
￥7,776
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
￥10,632
per adult
1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar
￥41,101
per adult
100% of travellers recommend
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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.
