Top Luxury Florida Keys Vacation Packages

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Flight and Luxury hotel deals in Florida Keys

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

Hawks Cay Resort

Save 100% on your flight
CA $1,789
per person
Nov 8 - Nov 14
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (1,002 reviews)
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight
CA $1,812
per person
Nov 8 - Nov 14
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,006 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $1,924
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $2,162
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Clean.helpful staff.good a/c.good location.will definitely stay here again.

Reviewed on Oct 1, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $1,928
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

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5* Luxury holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $3,106
per person
Nov 7 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Miami (MIA)
9.2/10 Wonderful! (1,451 reviews)
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3 Night Luxury holidays in Florida Keys

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

The Gardens Hotel

Old Town Key West
CA $1,924
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $2,880
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.6/10 Excellent! (3,606 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,506
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

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4 Night Luxury holidays in Florida Keys

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

Hawks Cay Resort

CA $1,400
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Miami (MIA)
8.2/10 Very good! (1,002 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

CA $1,471
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Miami (MIA)
9/10 Wonderful! (277 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $2,656
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
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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 $1,400, 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

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL
  • 10 min drive from Duval Street
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,800 reviews)
"The location was good. Our room had a great view of the water. The shower had lots of water pressure which was nice. The air conditioning was not good. We could not contol temperature, our room was too warm. I did not like the coffee maker in a drawer. The staff forgot to replish the coffee, etc. ..."

Reviewed on Sep 29, 2026

Hilton Key West Resort & Marina
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

200 William Street Key West FL
  • 10 min walk from Duval Street
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9.2/10 Wonderful! (1,031 reviews)
"Clean.helpful staff.good a/c.good location.will definitely stay here again."

Reviewed on Oct 1, 2026

The Marker Key West Harbor Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 3 hours drive from Duval Street
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
See all 8,253 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.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $82
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Florida Keys

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.