Florida Keys Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Luxury hotel deals in Florida Keys
Southernmost House - Adult Exclusive
Reviewed on 16 Aug 2026
Southernmost Beach Resort and Guesthouses
Reviewed on 16 Aug 2026
Cheeca Lodge & Spa
Reviewed on 17 Aug 2026
La Concha Key West, Autograph Collection
Reviewed on 13 Aug 2026
5* Luxury holidays in Florida Keys
Cheeca Lodge & Spa
Reviewed on 17 Aug 2026
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 £1,273. 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
Hilton Key West Resort & Marina
- 10 min drive from Duval Street
The Marker Key West Harbor Resort
- 10 min walk from Duval Street
"Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees."
Reviewed on 14 Aug 2026
Cheeca Lodge & Spa
- 3 hours drive from Duval Street
"The pools and bars were great! Our room was dirty, our toilet base was broken, in room coffee pot was HORRIBLE! The food there is ok, I recommend eating out at least for dinners. The bar service while at the pool was the absolute best part. Butch was the best bartender!"
Reviewed on 17 Aug 2026
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
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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.
