Title: Luxury Florida Keys Vacation Packages 2026/2026 | Expedia.ca

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# Top Luxury Florida Keys Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Save up to CA $1,096 when you book a flight and hotel together\*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Plan, book, and manage your trip all in one place

## Flight and Luxury hotel deals in Florida Keys

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

![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

CA $1,345

per person

Jan 11 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Miami (MIA)

8.8/10 Excellent! (1,275 reviews)

Excellent experience. Excellent staff Ultra clean All in all, great location, ambiance and value.

Reviewed on Dec 7, 2025

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $1,836

per person

Feb 11 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Beautiful balcony and porch views.

Reviewed on Dec 8, 2025

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $4,181

per person

Feb 11 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Everything was awsome

Reviewed on Dec 7, 2025

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans Edge Key West Resort, Hotel & Marina

CA $1,472

per person

Feb 11 - Feb 15

found 3 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

Rooms were beautiful

Reviewed on Dec 9, 2025

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

CA $3,370

per person

Feb 13 - Feb 19

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

Would recommend for family and friends. Nice and relaxing

Reviewed on Dec 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Luxury holidays in Florida Keys

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $4,181

per person

Feb 11 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Buffalo (BUF) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Everything was awsome

Reviewed on Dec 7, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Luxury holidays in Florida Keys

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $1,599

per person

Feb 13 - Feb 16

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Beautiful balcony and porch views.

Reviewed on Dec 8, 2025

![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/424c57d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Gardens Hotel

Old Town Key West

CA $2,076

per person

Feb 20 - Feb 23

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there

Reviewed on Nov 20, 2025

![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Tranquility Bay Beachfront Hotel and Resort

CA $1,742

per person

Feb 20 - Feb 23

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (1,003 reviews)

Would recommend for family and friends. Nice and relaxing

Reviewed on Dec 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Luxury holidays in Florida Keys

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

![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hawks Cay Resort

CA $939

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

8/10 Very Good! (1,003 reviews)

Beautiful balcony and porch views.

Reviewed on Dec 8, 2025

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans Edge Key West Resort, Hotel & Marina

CA $1,472

per person

Feb 11 - Feb 15

found 3 hours ago

Roundtrip flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

Rooms were beautiful

Reviewed on Dec 9, 2025

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

CA $3,590

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Everything was awsome

Reviewed on Dec 7, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 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 $939, 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 37\. 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

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oceans Edge Key West Resort, Hotel & 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 ...

8.8/10 Excellent! (1,746 reviews)

Rooms were beautiful

Reviewed on Dec 9, 2025

[](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information)

![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 ...

9/10 Wonderful! (1,000 reviews)

Loved this hotel. Staff was very friendly, rooms were clean and property is very nice. Location and parking for hotel guests. Can say enough will definitely return.

Reviewed on Dec 3, 2025

[](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information)

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 ...

9.2/10 Wonderful! (1,268 reviews)

Everything was awsome

Reviewed on Dec 7, 2025

[](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)

[See all 8,379 properties in Florida Keys](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6023765)

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.

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## More Vacations Ideas

[Flights to Florida Keys

](https://expedia.ca/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[

Florida Keys Hotels

](https://expedia.ca/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[

Florida Keys Vacation Rentals

](https://expedia.ca/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[

Florida Keys Car Rentals

](https://expedia.ca/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[

Florida Keys Vacations

](https://expedia.ca/Florida-Keys.d6023765.Destination-Travel-Guides)[

Things to do in Florida Keys

](https://expedia.ca/Things-To-Do-In-Florida-Keys.d6023765.Travel-Guide-Activities)

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

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