Florida Keys Luxury Vacations 2026

Top Luxury vacation packages in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$342

per person

Nov 15 - Nov 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Resort exceeded expectations for Islamorada area, well maintained, great location and excellent amenities. Great sunrise every morning.

Reviewed on Oct 14, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,027

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

I didnt like this property at all

Reviewed on Oct 13, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$953

per person

Nov 15 - Nov 18

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

$893

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

A perfect get away place to stay for couples & families. Clean rooms, friendly staff & lots of great accommodations for everyone!

Reviewed on Oct 15, 2026

Hawks Cay Resort

$774

per person

Dec 15 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Harrisburg (MDT) to Miami (MIA)

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

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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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

$342

per person

Nov 15 - Nov 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Resort exceeded expectations for Islamorada area, well maintained, great location and excellent amenities. Great sunrise every morning.

Reviewed on Oct 14, 2026

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.

Southernmost Beach Resort and Guesthouses

Old Town Key West

$893

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Key West (EYW)

8.6/10 Excellent! (3,636 reviews)

A perfect get away place to stay for couples & families. Clean rooms, friendly staff & lots of great accommodations for everyone!

Reviewed on Oct 15, 2026

The Marker Key West Harbor Resort

Key West Historic District

$1,027

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Key West (EYW)

9.2/10 Wonderful! (1,024 reviews)

I didnt like this property at all

Reviewed on Oct 13, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$953

per person

Nov 15 - Nov 18

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Luxury vacations in Florida Keys

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

Drop Anchor

Save 100% on your flight

$517

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Miami (MIA)

8.6/10 Excellent! (1,002 reviews)

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

Save 100% on your flight

$851

per person

Dec 16 - Dec 20

found 9 hours ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Hawks Cay Resort

Save 100% on your flight

$813

per person

Dec 16 - Dec 20

found 9 hours ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

8.2/10 Very Good! (1,006 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 $342. 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 ...

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! (1,033 reviews)

"I didnt like this property at all"

Reviewed on Oct 13, 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! (1,482 reviews)

"Resort exceeded expectations for Islamorada area, well maintained, great location and excellent amenities. Great sunrise every morning."

Reviewed on Oct 14, 2026

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.