Islamorada Vacations from ￥118,015
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The Latest Islamorada Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hollywood Beach Seagull
Hollywood Beach
Price was ￥146,716, price is now ￥118,015 per person
￥118,015
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
6.8/10 (392 reviews)
Location,Location, Location..just keep telling that to yourself. Staff were pleasant and helpful. Towels were scarce. No handtowels. No dish cloths/towels. Our dishwasher leaked. Two burners on the stove did not work. Kitchen is totally empty. If you want dishes, you must call and then you are given the bare basics. Rooms are very dated and in need of repairs. Everything was clean. Bed and pillows comfortable. Breakfast was basic, but all that we needed. Directly on the boardwalk and beach. Felt quite safe. If you are looking for fine accomodations, dont stay here. If you can be low maintenance and love the beach, it is perfect.
Reviewed on Jan 8, 2026
CH Luxury Condos & Studios On The Beach
Hollywood Beach
Price was ￥251,178, price is now ￥192,725 per person
￥192,725
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.4/10 Very Good! (126 reviews)
Simply... What a rental condo/resort should be!
Reviewed on Nov 11, 2025
Costa Hollywood Beach Resort
Hollywood Beach
Price was ￥239,046, price is now ￥183,730 per person
￥183,730
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
9/10 Wonderful! (3,848 reviews)
Nice big room. Great location, pool.
Reviewed on Jan 11, 2026
Paradise Oceanfront HBH
Hollywood Beach
Price was ￥159,552, price is now ￥132,038 per person
￥132,038
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
6.6/10 (320 reviews)
the problem is that the door frame and lock were insecure, and the bed sheet and duvet although they seemed clean, had an extremely strong smell of cleaning fluid, which caused me a headache and did not let myself sleep to the point that I only slept one night of the two I had paid for and left that hotel.
Reviewed on Nov 29, 2025
Hollywood Beachside Boutique Suites
Hollywood Beach
Price was ￥146,626, price is now ￥121,396 per person
￥121,396
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.8/10 Excellent! (3,270 reviews)
Nice place , very clean , perfect location,
Nice staff. Definitely will be back
Reviewed on Jan 11, 2026
Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
5 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 ￥28,655 per night from Jan 28 to Jan 29
￥28,655
￥41,119 total
Jan 28 - Jan 29
includes taxes & fees
9.2/10 Wonderful! (1,626 reviews)
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good
Reviewed on Jan 11, 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 ￥46,838 per night from Jan 21 to Jan 22
￥46,838
￥63,173 total
Jan 21 - Jan 22
includes taxes & fees
8.8/10 Excellent! (124 reviews)
Amazing place - so much variety
Reviewed on Jan 6, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥38,539 per night from Jan 29 to Jan 30
￥38,539
￥54,903 total
Jan 29 - Jan 30
includes taxes & fees
9.2/10 Wonderful! (1,288 reviews)
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family
Reviewed on Jan 11, 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
￥10,803
per adult
96% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
￥7,672
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
￥10,490
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.
