Islamorada Luxury Holidays

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

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top flight + Luxury hotel deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Cheeca Lodge & Spa
Islander Resort
La Siesta Resort & Villas
Don't see what you're looking for?
See all available trips from New York to Islamorada
View all trips

5* Luxury holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Don't see what you're looking for?
See all available trips from New York to Islamorada
View all trips

3 Night Luxury holidays in Islamorada

Price found within the past 48 hours. Click for updated prices.
La Siesta Resort & Villas
Cheeca Lodge & Spa
Islander Resort
Don't see what you're looking for?
See all available trips from New York to Islamorada
View all trips

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 £386. 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, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
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 ...
9/10 Wonderful! (1,112 reviews)
"Good pool should stay open later for adults"

Reviewed on 3 Jul 2025

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 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 their reviews. ...
8.8/10 Excellent! (1,221 reviews)
"Place was clean and the amenities are really nice. This is our third time in this hotel and we missed the store to buy essentials and souvenirs and we missed also the ice creams options, the ice cream fridge was empty."

Reviewed on 30 Jun 2025

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 3-star 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 ...
8.8/10 Excellent! (1,001 reviews)
"Compared to other choices in the area, I thought we ended with the best deal. We booked the ocean view king room, which is very spacious with sitting area and the view of the water is right there. Nice updated bathroom and a balcony overlooking the water too. Freshly painted inside and out - well ..."

Reviewed on 3 Jul 2025

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.

More holidays you might like

* 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.