Islamorada Holidays from NZ$2,702
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The Latest Islamorada Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
per person
12 Aug - 19 Aug
found 12 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.
Reviewed on 1 Jul. 2025
Fontainebleau Miami Beach
Mid Beach
per person
12 Aug - 19 Aug
found 12 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Everything you need is there. However for the amount of money you pay, you would expect the washrooms to be clean when you arrive to your room at check-in. We ordered additional glasses and they were dirty. Staff did get us more glasses but again, for the price we paid, you would expect them to already be clean. Additionally, the fridge was also not working. We called and they told us 3 times they would send someone - no one showed up. Property and amenities were great. Staff was also great.
Reviewed on 10 Jul. 2025
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 Anne's Beach 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, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$437 per night from 6 Aug to 7 Aug
NZ$437
6 Aug - 7 Aug
includes taxes & fees
9/10 Wonderful! (1,119 reviews)
"First time, we enjoyed it"
Reviewed on 7 Jul. 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$527 per night from 23 July to 24 July
NZ$527
23 July - 24 July
includes taxes & fees
9/10 Wonderful! (1,482 reviews)
"The property is nice. Water pressure was not great. Water stopped completely while in the shower on multiple occasions. It was not off long but it was completely off. It was nice that breakfast was served a bit later, but even by 9 some things were gone. Overall nice stay."
Reviewed on 6 Jul. 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$502 per night from 4 Aug to 5 Aug
NZ$502
4 Aug - 5 Aug
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Fabulous vacation experience! Beautiful facilites with phenomenal ocean views!!!"
Reviewed on 10 Jul. 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.
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
Original Snorkel and Sandbar Combo in Islamorada
NZ$248
per adult
90% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
NZ$832
per traveller
100% of travellers recommend
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
NZ$414
per adult
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.