Islamorada Holiday Packages

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Islamorada Accommodation

Wotif lists 24 accommodation in Islamorada. Narrow down your search and nab a terrific deal today.

Yearning for a taste of the good life? Tempted to indulge yourself while you're away? Book a swanky room at the Cheeca Lodge & Spa (81801 Overseas Highway, Mile Marker 82), and you'll feel like a VIP. Come on — you deserve it. If you're after something more comfy and easy on your bank balance, we've got a couple of fantastic options as well. Start with the Hadley House Islamorada (82749 Overseas Hwy).

Car Hire in Islamorada

Budget (9400 Overseas Hwy) is the nearest car rental company to Florida Keys Marathon Airport. Take an easy taxi drive there and you'll be cruising down the road in no time.

Holidays to Islamorada

Booked that window seat, packed your fave thongs but don't know the first thing about Islamorada? Listen up. We can tell you a thing or two about this awesome destination.

Want to visualise where you'll be based? Islamorada is 270 kilometres northeast of the popular city of Havana.

Flying solo? Keen to get acquainted with some of the locals? With approximately 7 000 people living in this part of Florida Keys, you're sure to make some new friends.

Top Islamorada hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$479 per night from 21 May to 22 May
NZ$479
21 May - 22 May
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Our stay at Chesapeake Beach Resort was absolutely amazing from start to finish! The check-in process was quick and easy, and every staff member made us feel so welcomed and accommodated throughout our stay. The complimentary breakfast each morning was fresh and delicious. I had a made-to-order omelet ...

Reviewed on 16 May 2026

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$509 per night from 21 May to 22 May
NZ$509
21 May - 22 May
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
I can't say enough good things about the Cheeka Lodge and Spa! The room was beautiful, the staff were amazing, amd the food was spectacular! Highly recommend!

Reviewed on 15 May 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$521 per night from 31 May to 1 June
NZ$521
31 May - 1 June
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
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Reviewed on 16 May 2026

Opens in a new windowIslander Resort
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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.

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