Florida Keys Luxury Holidays

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Top flight + Luxury hotel deals in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Hawks Cay Resort
Pier House Resort & Spa
Tranquility Bay Beachfront Hotel and Resort
Southernmost Beach Resort
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5* Luxury holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
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4 Night Luxury holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Hawks Cay Resort
Pier House Resort & Spa
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All you need to know about luxury holidays in Florida Keys

What can I expect from a luxury Florida Keys 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 Florida Keys?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Florida Keys 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 Florida Keys?

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 Florida Keys starting at £894. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Florida Keys?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Florida Keys 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 Florida Keys?

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 Florida Keys?

You can wangle a top-notch luxury holiday in Florida Keys 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 Florida Keys 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 Florida Keys with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Florida Keys 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 Florida Keys Hotels

Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
  • 10 min drive from Duval Street
Stay at this 4-star luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. ...
8.8/10 Excellent! (1,642 reviews)
"We loved the location of the Resort and the "chill" vibe it provided. The hourly shuttle to and from downtown Key West was a GREAT asset and we utilized it everyday. We also took advantage of the bicycles to get to lunch (at Hog Fish) and the kayaks. My only frustration is that we must have missed ..."

Reviewed on 23 Apr 2025

Oceans Edge Key West Resort, Hotel & Marina
The Marker Key West Harbor Resort
The Marker Key West Harbor Resort
4 out of 5
200 William Street, Key West, FL
  • 10 min walk from Duval Street
Stay at this 4-star eco-certified hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and breakfast (surcharge). Our guests praise the pool and the bar in their ...
8.8/10 Excellent! (1,002 reviews)
Great location.
"Beds were very comfortable. Carpets could use a good wash. Super convenient location to Key West Express. Early check in wasn’t available but they did check your bags for the day both coming and going and allowed you to use the amenities. Very helpful for an overnight stay."

Reviewed on 21 Apr 2025

The Marker Key West Harbor Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 3 hours drive from Duval Street
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! (1,064 reviews)
"Need complete refund ASAP"

Reviewed on 23 Apr 2025

Cheeca Lodge & Spa
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.