Islamorada Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 Robbie’s of Islamorada 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$456 per night from 14 July to 15 July
NZ$456
14 July - 15 July
includes taxes & fees
9.2/10 Wonderful! (1,759 reviews)
"Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here."
Reviewed on 15 June 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$531 per night from 6 July to 7 July
NZ$531
6 July - 7 July
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
"We had a wonderful stay and really loved the resort. The room and balcony were absolutely perfect. My one suggestion would be to consider making one of the two beachfront pools adults-only. There is already an adults-only pool on the property, which is a nice option, but it’s located in the middle ..."
Reviewed on 15 June 2026
Islander Resort
82100 Overseas Highway Islamorada FL
The price is NZ$609 per night from 7 July to 8 July
NZ$609
7 July - 8 July
includes taxes & fees
9.4/10 Exceptional! (1,056 reviews)
"We were only there one night."
Reviewed on 15 June 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.
Stay near popular Islamorada attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
