
Florida Keys Luxury Vacations
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Top Luxury vacation packages in Florida Keys

The Gardens Hotel
Reviewed on Aug 25, 2026


Hawks Cay Resort
Reviewed on Aug 26, 2026

Tranquility Bay Beachfront Hotel and Resort
Reviewed on Aug 27, 2026

5* Luxury vacations in Florida Keys

3 Night Luxury vacations in Florida Keys


Hawks Cay Resort
Reviewed on Aug 26, 2026

Tranquility Bay Beachfront Hotel and Resort
Reviewed on Aug 27, 2026
4 Night Luxury vacations in Florida Keys

Azul del Mar
Reviewed on Aug 25, 2026


Hawks Cay Resort
Reviewed on Aug 26, 2026
All you need to know about luxury vacations in Florida Keys
What can I expect from a luxury Florida Keys vacation?
Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Florida Keys vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views.
How can I find all-inclusive luxury vacation packages in Florida Keys?
By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger.
Can I book a cheap Florida Keys luxury vacation?
Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $389. Prices and availability are subject to change. Additional terms may apply.
How can I book a luxury family vacation in Florida Keys?
Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi.
Can I book a package in Florida Keys with a luxury vacation home?
A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.
How can I find the best luxury vacation deals in Florida Keys?
Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.
Can I book a luxury holiday in Florida Keys with free cancellation and/or flexible dates?
Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan.
Why should I book my luxury trip to Florida Keys with Expedia?
A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.
Top Luxury Florida Keys Hotels

Hilton Key West Resort & Marina
- 10 min drive from Duval Street
"Agustín at the front desk always making sure everything was good.. they are finally remodeling the place. It needed a touch up already. Still place is clean."
Reviewed on Aug 25, 2026

The Marker Key West Harbor Resort
- 10 min walk from Duval Street
"This is our second time staying at The Marker and we will definitely be back! It is convenient to everything Key West has to offer. The staff goes above and beyond to accommodate whatever you need and we couldn't be happier with our stay!"
Reviewed on Aug 26, 2026

Cheeca Lodge & Spa
- 3 hours drive from Duval Street
"Trip was exceptional"
Reviewed on Aug 27, 2026
Things to do

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

Key West Rum & Reggae: Snorkel & Sunset Sail Combo
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