A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Top Luxury Florida Keys Vacation Packages

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Top Luxury vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.
  • Jan 9 - Jan 12

    Hawks Cay Resort + Flight

    Marathon
    3 nights
    4.0 star property
    8.2/10 - Very good (1,003 reviews)
    "This resort never disappoints! Love the property, amenities, and the adult pool"
    Reviewed November 2, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - FLL • 1 stop FLL - YUL • 1 stop
    CA $1,612
    CA $1,178
    per traveller
    found 1 hour ago
    Hawks Cay Resort
  • Jan 7 - Jan 11

    Cheeca Lodge & Spa + Flight

    Matecumbe
    4 nights
    5.0 star property
    9.2/10 - Wonderful (1,508 reviews)
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    Save 100% on your flight
    CA $2,240
    CA $1,544
    per traveller
    found 1 day ago
    Cheeca Lodge & Spa
  • Jan 7 - Jan 11

    Villas At Hawks Cay Resort + Flight

    Marathon
    4 nights
    4.0 star property
    8.0/10 - Very good (233 reviews)
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    Save 100% on your flight
    CA $2,186
    CA $1,600
    per traveller
    found 1 day ago
    Villas At Hawks Cay Resort
  • Jan 9 - Jan 12

    Isla Bella Beach Resort & Spa + Flight

    Marathon
    3 nights
    5.0 star property
    9.2/10 - Wonderful (1,302 reviews)
    "Amazing hotel"
    Reviewed November 5, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - FLL • 1 stop FLL - YUL • 1 stop
    CA $1,785
    CA $1,340
    per traveller
    found 1 hour ago
    Isla Bella Beach Resort & Spa
  • Jan 7 - Jan 11

    The Islands of Islamorada + Flight

    Matecumbe
    4 nights
    5.0 star property
    9.6/10 - Exceptional (83 reviews)
    "We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
    Reviewed October 30, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    Save 100% on your flight
    CA $6,683
    CA $5,083
    per traveller
    found 1 day ago
    The Islands of Islamorada

Discover the most popular places to visit in Florida Keys

What to do in Florida Keys

Top Luxury Florida Keys Hotels

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.

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 $1,178, 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 26. 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.