Florida Keys Luxury Vacations

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Top Luxury vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hawks Cay Resort
Cheeca Lodge & Spa
Tranquility Bay Beachfront Hotel and Resort
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
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5* Luxury vacations in Florida Keys

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Cheeca Lodge & Spa
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3 Night Luxury vacations in Florida Keys

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Hawks Cay Resort
Cheeca Lodge & Spa
Oceans Edge Key West Resort, Hotel & Marina
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4 Night Luxury vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Cheeca Lodge & Spa
Hawks Cay Resort
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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 $551. 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

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
Pamper yourself with a luxury stay at Oceans Edge Key West Resort, Hotel & Marina, where you can enjoy amenities like Egyptian cotton sheets, plush bedding, ...
8.8/10 Excellent! (1,778 reviews)
The staff was outstanding, rooms were clean and beautiful and food was excellent. All around a great hotel!

Reviewed on Jan 11, 2026

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
Be treated to a grand stay at The Marker Key West Harbor Resort, where you'll find deep soaking bathtubs and premium bedding. The 3 outdoor pools, poolside bar, ...
9/10 Wonderful! (1,018 reviews)
Staff helpful and attentive during check in

Reviewed on Jan 12, 2026

The Marker Key West Harbor Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 3 hours drive from Duval Street
Cheeca Lodge & Spa is a Islamorada luxury 5-star beach property where you can treat yourself to Champagne service, massage services, and more. The 2 poolside ...
9.2/10 Wonderful! (1,288 reviews)
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

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 vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.