Florida Keys Luxury Vacations 2026

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Top Luxury vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.

The Gardens Hotel

Old Town Key West

$695

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

We had an amazing three night stay. It was a quiet place and the rooms were amazing! We highly recommend this place. Location is good.

Reviewed on Aug 25, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$742

per person

Oct 29 - Nov 1

found 4 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Trip was exceptional

Reviewed on Aug 27, 2026

Hawks Cay Resort

Save 100% on your flight

$734

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

I was really enjoying my time at Hawks Cay Resort. The views here were absolutely breathtaking! 🌴🌊😍 I just wanted to relax, enjoy the beautiful scenery, and make the most of every moment of my vacation.

Reviewed on Aug 26, 2026

Tranquility Bay Beachfront Hotel and Resort

$1,037

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

This was a very nice property. Very well maintained. Our 3 bedroom villa was very clean. Had all essential cookware in the kitchen. New coffee packs were provided every day. The housekeepers came in and tidied and changed the towels daily emptied garbage etc.. Sheets are changed after 4 days. 2 pool options. A adult only pool and the main pool. There is a private Beach area with lounges. Great local restaurants all around. Keywest about an hour away.

Reviewed on Aug 27, 2026

Amara Cay Resort

Matecumbe

$807

per person

Oct 28 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Madison (MSN) to Miami (MIA)

8.8/10 Excellent! (1,287 reviews)

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5* Luxury vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$742

per person

Oct 29 - Nov 1

found 4 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Trip was exceptional

Reviewed on Aug 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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3 Night Luxury vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$389

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip flight included

Houston (HOU) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Trip was exceptional

Reviewed on Aug 27, 2026

Hawks Cay Resort

Save 100% on your flight

$392

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip flight included

Houston (HOU) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

Reviewed on Aug 26, 2026

Tranquility Bay Beachfront Hotel and Resort

$741

per person

Oct 30 - Nov 2

found 1 hour ago

Roundtrip flight included

St. Louis (STL) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Reviewed on Aug 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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4 Night Luxury vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.

Azul del Mar

Save 100% on your flight

$561

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Miami (MIA)

9/10 Wonderful! (879 reviews)

Nothing good to say about the drive and FL. However, the room: clean, comfy. No staff, really- just AI. It was good enough for our diving trip. The room was spacious but had thin walls (we heard the tenants next door all night). The groomed beach and dock wall out front were great.

Reviewed on Aug 25, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,233

per person

Nov 2 - Nov 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Trip was exceptional

Reviewed on Aug 27, 2026

Hawks Cay Resort

Save 100% on your flight

$734

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

Reviewed on Aug 26, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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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

5950 Peninsular Avenue Key West FL

10 min drive from Duval Street

Pamper yourself with a luxury stay at Hilton Key West Resort & Marina, where you can enjoy amenities like Egyptian cotton sheets, plush bedding, and more. Deluxe ...

9/10 Wonderful! (1,826 reviews)

"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

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, ...

9.2/10 Wonderful! (1,028 reviews)

"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

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! (1,429 reviews)

"Trip was exceptional"

Reviewed on Aug 27, 2026

See all 8,256 properties in Florida Keys

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.