Islamorada Holidays from NZ$3,265
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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
Price was NZ$5,350, price is now NZ$3,576 per person
NZ$3,576
per person
20 Apr - 27 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places.
I really enjoyed my stay and would definitely recommend this hotel to others.
Reviewed on 26 Jan 2026
Flow Miami Hotel
Downtown Miami
Price was NZ$4,834, price is now NZ$3,374 per person
NZ$3,374
per person
20 Apr - 27 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.2/10 Wonderful! (172 reviews)
Beautiful clean room/apartment. Loved the location and view at night. We walked to our cruise. Staff was also very friendly and helpful. Would stay here again!
Reviewed on 25 Jan 2026
Pelican Hotel
South Beach
Price was NZ$4,987, price is now NZ$3,489 per person
NZ$3,489
per person
20 Apr - 27 Apr
found 24 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.
Reviewed on 12 Jan 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
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.
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
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$511 per night from 2 Feb to 3 Feb
NZ$511
2 Feb - 3 Feb
includes taxes & fees
9.2/10 Wonderful! (1,652 reviews)
The workers were excellent. The breakfast staff were wonderful. Chris, Didi,Emily. The were so helpful. You have a great bunch of workers. I can't say enough about the staff.
Reviewed on 23 Jan 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$691 per night from 3 Feb to 4 Feb
NZ$691
3 Feb - 4 Feb
includes taxes & fees
9.2/10 Wonderful! (1,300 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.
Reviewed on 22 Jan 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 NZ$769 per night from 29 Jan to 30 Jan
NZ$769
29 Jan - 30 Jan
includes taxes & fees
9/10 Wonderful! (134 reviews)
Great place
Reviewed on 22 Jan 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$85
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
NZ$116
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
NZ$391
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.
