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$383 per night from 10 Nov to 11 Nov
NZ$383
10 Nov - 11 Nov
includes taxes & fees
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Great hotel and stuff

Reviewed on 3 Nov 2025

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$490 per night from 20 Nov to 21 Nov
NZ$490
20 Nov - 21 Nov
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Jess was great when checked in, made us feel right at home. The entire resort is beautiful, clean, well maintained. Although the rooms are spacious they’re starting to show their wear and tare, carpets needs a good cleaning or just install tile. Butch and Cole are great at the pool bar and as always ...

Reviewed on 3 Nov 2025

Opens in a new windowCheeca Lodge & Spa
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$412 per night from 3 Dec to 4 Dec
NZ$412
3 Dec - 4 Dec
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
Great stay except for the fact that we could not watch the World Series in the comfort of our room!! Really? Other than that thoughtless error our stay was relaxing and fun.

Reviewed on 3 Nov 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.