Islamorada Luxury Holidays

Book a Luxury Hotel + Flight or Car together to unlock savings

Top flight + Luxury hotel deals in Islamorada

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Cheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islander Resort
La Siesta Resort & Villas
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5* Luxury holidays in Islamorada

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Cheeca Lodge & Spa
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3 Night Luxury holidays in Islamorada

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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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All you need to know about luxury holidays in Islamorada

What can I expect from a luxury Islamorada holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Islamorada?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Islamorada holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Islamorada?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Islamorada starting at £1,000. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Islamorada?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Islamorada spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Islamorada?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Islamorada?

You can wangle a top-notch luxury holiday in Islamorada for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Islamorada with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Islamorada with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Islamorada to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Islamorada Hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 8 min drive from Theater of the Sea
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 ...
9.2/10 Wonderful! (1,328 reviews)
Beautiful!!!

Reviewed on 7 May 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
  • 12 min drive from Theater of the Sea
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. ...
8.8/10 Excellent! (1,277 reviews)
I enjoyed my proximity to the beach into the pool area and the room was nicely appointed!

Reviewed on 7 May 2026

Amara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
  • 8 min walk from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and free bicycles on-site. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (1,002 reviews)
Our room was comfortable and clean. The grounds and pool were really nice. The entire staff were awesome. It was really cool having the kayaks on the property. We had a great stay.

Reviewed on 26 Apr 2026

Drop Anchor
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.