Florida Keys Luxury Vacations 2026

Top Luxury vacation packages in Florida Keys

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

Hawks Cay Resort

$787

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Miami (MIA)

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

Over priced for quality of rooms.

Reviewed on Oct 18, 2026

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$1,089

per person

Dec 22 - Dec 25

found 21 hours ago

Roundtrip flight included

Minneapolis (MSP) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

My husband injured his foot 6 days before our vacation snd had to wear a boot and use a knee scooter. I called Tranquility and asked to change to a handicap room. The gal said there was availability but I would need to call Hotel.com as I had reserved thru them. I couldn’t find a phone number so had to chat online with someone at Hotels. He said he would contact Tranquility, but he would not give me a phone number to talk to someone in charge. I called Tranquility back to say I chatted with Hotel and did as they asked. She said she would transfer the request to the correct department. When we arrived there was no handicap room available

Reviewed on Oct 18, 2026

Cheeca Lodge & Spa

Matecumbe

$840

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

The Gardens Hotel

Old Town Key West

$1,778

per person

Dec 19 - Dec 22

just found

Roundtrip flight included

Charlotte (CLT) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

The room was cute and very clean. Overall stay was nice.

Reviewed on Oct 18, 2026

Southernmost House - Adult Exclusive

Old Town Key West

$1,266

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

Liked the bungalow, smaller but functional. The only problem I had was the air conditioning couldn’t cool the room efficiently and had to keep emptying the dehumidifier. Love the location, pool and hotel.

Reviewed on Oct 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

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

$1,440

per person

Dec 19 - Dec 23

found 15 hours ago

Roundtrip non-stop flight included

Dayton (DAY) 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.

Cheeca Lodge & Spa

Matecumbe

$840

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Miami (MIA)

9.2/10 Wonderful! (1,471 reviews)

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$1,089

per person

Dec 22 - Dec 25

found 21 hours ago

Roundtrip flight included

Minneapolis (MSP) to Miami (MIA)

8.8/10 Excellent! (1,006 reviews)

Reviewed on Oct 18, 2026

The Gardens Hotel

Old Town Key West

$1,778

per person

Dec 19 - Dec 22

just found

Roundtrip flight included

Charlotte (CLT) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

The room was cute and very clean. Overall stay was nice.

Reviewed on Oct 18, 2026

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.

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

Save 100% on your flight

$1,008

per person

Nov 19 - Nov 23

found 19 hours ago

Roundtrip non-stop flight included

Cedar Rapids (CID) to Miami (MIA)

9/10 Wonderful! (281 reviews)

Lime Tree Bay Resort

Save 100% on your flight

$1,175

per person

Dec 24 - Dec 28

found 12 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

9.4/10 Exceptional! (1,527 reviews)

Hawks Cay Resort

Save 100% on your flight

$1,059

per person

Nov 19 - Nov 23

found 19 hours ago

Roundtrip non-stop flight included

Cedar Rapids (CID) to Miami (MIA)

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

Over priced for quality of rooms.

Reviewed on Oct 18, 2026

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 $787. 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! (1,032 reviews)

"Excellent place to stay. Conveniently located to Duval Street."

Reviewed on Oct 19, 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 ...

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.