Top Luxury Florida Keys Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Flight and Luxury hotel deals in Florida Keys

Hawks Cay Resort
Southernmost Beach Resort
The Gates Hotel Key West
24 North Hotel Key West
Oceans Edge Key West Resort, Hotel & Marina
Don't see what you're looking for?
See all available trips from Ashburn to Florida Keys
View all trips
Prices and availability subject to change. Additional terms may apply.

5* Luxury holidays in Florida Keys

Casa Marina Key West, Curio Collection by Hilton
Don't see what you're looking for?
See all available trips from Ashburn to Florida Keys
View all trips
Prices and availability subject to change. Additional terms may apply.

3 Night Luxury holidays in Florida Keys

Hawks Cay Resort
Faro Blanco Resort & Yacht Club
Oceans Edge Key West Resort, Hotel & Marina
Tranquility Bay Beachfront Hotel and Resort
Cheeca Lodge & Spa
Don't see what you're looking for?
See all available trips from Ashburn to Florida Keys
View all trips
Prices and availability subject to change. Additional terms may apply.

4 Night Luxury holidays in Florida Keys

Hawks Cay Resort
The Gates Hotel Key West
Almond Tree Inn Hotel - Adults Only
Oceans Edge Key West Resort, Hotel & Marina
Lime Tree Bay Resort
Don't see what you're looking for?
See all available trips from Ashburn to Florida Keys
View all trips
Prices and availability subject to change. Additional terms may apply.

Plan the perfect luxury Florida Keys vacation with Expedia

What are some benefits when booking luxury Florida Keys vacations?

When you book a luxury Florida Keys vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.


How can I find all-inclusive luxury vacations in Florida Keys?

If you're looking for something luxurious in Florida Keys, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $929, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 22. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Florida Keys. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Florida Keys?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Florida Keys.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Florida Keys. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Florida Keys?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Florida Keys or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Florida Keys. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Florida Keys

Little Palm Island Resort & Spa - A Noble House Resort
Little Palm Island Resort & Spa - A Noble House Resort
4.5 out of 5
28500 Overseas Hwy, Summerland Key, FL
  • 1 hour drive from Duval Street
Stay at this beach resort in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Popular attractions Big Pine Key Flea Market and National Key ...
9.8/10 Exceptional! (42 reviews)
"fabulous accommodation and staff...service is superb"

Reviewed on Jul. 3, 2017

Little Palm Island Resort & Spa - A Noble House Resort
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
Stay at this 4-star golf hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the bar in our reviews. Popular attractions ...
8.8/10 Excellent! (1,561 reviews)
"Staff was amazing ! Thank you for a memorable stay"

Reviewed on Mar. 26, 2024

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
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast. Our guests praise the pool and the restaurant in our ...
8.6/10 Excellent! (1,001 reviews)
"Very relaxing atmosphere. Walkable to most locations on the island. Well kept, clean, quiet, great pool areas.(3)"

Reviewed on Mar. 26, 2024

The Marker Key West Harbor Resort
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.