Florida Keys Luxury Vacations 2026

Top Luxury vacation packages in Florida Keys

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$351

per person

Dec 16 - Dec 18

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

Hawks Cay Resort

$835

per person

Dec 16 - Dec 20

found 10 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

8.2/10 Very Good! (1,006 reviews)

We love staying at Hawks Cay we have been going for years. The Property amenities are amazing. However, the Villa we stayed at (7039) was in horrible condition. Roaches in kitchen and bathroom, Shades on windows were broken in rooms. The jacuzzi outside was dirty and we were not able to use. We were extremely disappointed to have found it in that condition. I reported to the front office when we checked out. I didn't bother saying anything while there because I am pretty sure they didn't have another one available.

Reviewed on Oct 15, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$676

per person

Dec 16 - Dec 19

found 16 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9/10 Wonderful! (281 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$408

per person

Dec 16 - Dec 18

found 1 day ago

Roundtrip flight included

Tampa (TPA) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

Cheeca Lodge & Spa

Matecumbe

$711

per person

Dec 16 - Dec 19

found 16 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9.2/10 Wonderful! (1,471 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

$711

per person

Dec 16 - Dec 19

found 16 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

3 Night Luxury vacations in Florida Keys

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$676

per person

Dec 16 - Dec 19

found 16 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Cheeca Lodge & Spa

Matecumbe

$711

per person

Dec 16 - Dec 19

found 16 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,305

per person

Dec 16 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

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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.

The Pelican Key Largo Cottages

Save 100% on your flight

$278

per person

Nov 15 - Nov 19

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9/10 Wonderful! (1,010 reviews)

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$846

per person

Dec 16 - Dec 20

found 10 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Drop Anchor

$643

per person

Dec 16 - Dec 20

found 10 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Miami (MIA)

8.6/10 Excellent! (1,002 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

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 $278. 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! (1,793 reviews)

"Good"

Reviewed on Oct 15, 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, ...

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 ...

See all 8,301 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.