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$441 per night from 28 Jan to 29 Jan
NZ$441
28 Jan - 29 Jan 2026
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. ...
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They ...

Reviewed on 26 Dec 2025

Opens in a new windowChesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$722 per night from 6 Jan to 7 Jan
NZ$722
6 Jan - 7 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
No balcony. We walked out right to the beach. IT WAS EVEN BETTER!!

Reviewed on 27 Dec 2025

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$541 per night from 8 Jan to 9 Jan
NZ$541
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !

Reviewed on 28 Dec 2025

Opens in a new windowAmara Cay 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.