Islamorada Holidays from NZ$2,535
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The Latest Islamorada Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Eden Roc Miami Beach
Mid Beach
Price was NZ$4,666, price is now NZ$3,719 per person
NZ$3,719
per person
6 May - 12 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (3,196 reviews)
My husband and I enjoyed our stay so much! The staff was amazing! The drinks were 10/10!! Our room was clean and had an amazing view. Staff made sure we had clean towels and made our beds daily!! We would definitely like to be back soon!
Reviewed on 11 Mar 2026
72 Park - Miami Beach by Nomada
North Beach
Price was NZ$4,213, price is now NZ$3,463 per person
NZ$3,463
per person
6 May - 12 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.8/10 Excellent! (228 reviews)
Spacious room that included a washer and dryer, well stocked with necessities, everything clean and fresh.
Unfortunately the windows don’t seem to be double glazed and the street below is busy - lots of noise from motorbikes and sirens. Front desk staff were helpful but Nomada (the agent) were disorganized and difficult to get in touch with. Were it not for the excessive street noise, I’d come back.
Reviewed on 12 Mar 2026
Our guide on 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.
Islamorada Holiday
Islamorada Beach Holiday
Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. 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 kilometres from the town centre. 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 holiday homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour 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.
Our pick of the best Islamorada Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$708 per night from 12 Apr to 13 Apr
NZ$708
12 Apr - 13 Apr
includes taxes & fees
9.2/10 Wonderful! (1,298 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window
Reviewed on 12 Mar 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$519 per night from 14 Apr to 15 Apr
NZ$519
14 Apr - 15 Apr
includes taxes & fees
9.2/10 Wonderful! (1,666 reviews)
We upgraded to an Ocean View and it was fantastic! Nice quiet vacation and great location with walkable restaurants and bars. Breakfast was special with awesome omlets by Chris!!
Reviewed on 13 Mar 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$584 per night from 26 Mar to 27 Mar
NZ$584
26 Mar - 27 Mar
includes taxes & fees
8.8/10 Excellent! (1,252 reviews)
We had a partial view of ocean from our room. We did not use the pool but it was a decent looking. The staff was kind and professional. The room we had smelled of mold strongly.
Reviewed on 12 Mar 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.
Discover the most popular places to visit in Islamorada
Anne's Beach
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Windley Key Fossil Reef Geological State Park
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
History of Diving Museum
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
What to do in Islamorada
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
NZ$82
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
NZ$112
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
NZ$376
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.
