Islamorada Holiday Packages

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Islamorada Accommodation

Wotif lists 24 accommodations 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 AU$323 per night from 10 Nov to 11 Nov
AU$323
10 Nov - 11 Nov
includes taxes & fees
Chesapeake Beach Resort: Pet-friendly hotel with free breakfast and free WiFi. Located by the ocean.
"Our room wasn’t really just our room. It had a door to the adjacent room so they can make it a suite. It has a huge gap under both doors so you can hear our neighbor cough,talk, and listen to the tv. You can see the light from their room shining under in our room and see shadows when they in The ..."

Reviewed on 4 Nov 2026

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$437 per night from 29 Nov to 30 Nov
AU$437
29 Nov - 30 Nov
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort: Family-friendly resort with free WiFi and 3 outdoor pools. Located by the ocean.
"Rooms are too tiny. I was changed 3 times by my request. Finally i stayed in front of the beach with ocean view balcony it was only when i felt in a real hotel room, The Cove is like be on a Hialeah apartment. I was charged 5 different times on my credit card, and 4 days after checkout i still have ..."

Reviewed on 5 Nov 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio 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 AU$396 per night from 29 Nov to 30 Nov
AU$396
29 Nov - 30 Nov
includes taxes & fees
Cheeca Lodge & Spa: Luxury resort with free valet parking and 3 outdoor pools. Guests love the helpful staff!
Opens in a new windowCheeca Lodge & Spa
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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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