Title: Windley Key Vacation Packages & Trips 2026 from CA $1,093 | Expedia.ca

[Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windley Key Vacation Packages

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

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

## Top Windley Key Vacation Deals

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

![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel

South Beach

CA $1,093

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.4/10 Very Good! (1,775 reviews)

The showers don’t work. The sink is a small one for the pricing.

Reviewed on Dec 8, 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 $1,829

per person

Feb 20 - Feb 27

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

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

Beautiful balcony and porch views.

Reviewed on Dec 8, 2025

![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pelican Hotel

South Beach

CA $1,729

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

9.2/10 Wonderful! (394 reviews)

Staff was friendly, room was clean, bed was comfortable, and everything looked as pictured, but down-rated slightly because a couple of little wall fixtures were broken in the room and the chairs in the room were uncomfortable. BEWARE there is a daily resort fee hiding in the fine print that increases the cost of the room and there was no major amenity like a swimming pool or spa that seemed to justify this. Breakfast was not included in the price of stay.

Reviewed on Dec 8, 2025

![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cavalier Hotel South Beach

South Beach

CA $1,115

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Nice staff, great area

Reviewed on Dec 9, 2025

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $7,542

per person

Jan 21 - Jan 24

found 1 hour ago

Roundtrip flight included

Detroit (DTW) to Miami (MIA)

8/10 Very Good! (1 review)

## Ready to book your vacation to Windley Key?

Choose your dates

## Windley Key Hotel Deals

![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

CA $292

CA $420 total

Dec 18 - Dec 19

includes taxes & fees

9/10 Wonderful! (114 reviews)

Beautiful room, stunning views

Reviewed on Nov 19, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=11864&PinnedHotelID=11864&HadPinnedHotel=true&regionId=553248635976197663)

![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundable

CA $160

CA $225 total

Dec 18 - Dec 19

includes taxes & fees

8/10 Very Good! (1,000 reviews)

It was very nice to have light breakfast choices available along with free kayak and paddle boards to use. AC worked great! I chose a room with a view and I enjoyed it very much! Thank you

Reviewed on Dec 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=3274374&PinnedHotelID=3274374&HadPinnedHotel=true&regionId=553248635976197663)

![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

CA $197

CA $222 total

Dec 17 - Dec 18

includes taxes & fees

8.8/10 Excellent! (149 reviews)

Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall

Reviewed on Dec 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=4182524&PinnedHotelID=4182524&HadPinnedHotel=true&regionId=553248635976197663)

[See all 2,722 properties in Windley Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F12%2F2025&endDate=13%2F12%2F2025&regionId=553248635976197663)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Windley Key

![Windley Key Fossil Reef Geological State Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340296-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Windley Key Fossil Reef Geological State Park

Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

[](https://expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

## Frequently asked questions

### Can I cancel my flight booking to Windley Key due to COVID-19?

### What's the best way to find cheap flights to Windley Key that have flexible change policies?

### What are some of the general tips for travelers to Windley Key during the COVID-19 outbreak?

> - Look into what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check in advance.
> - When you pass through airport checkpoints, do not remove your face mask. You will be asked to briefly lower it for ID purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
> - Rather than handing a TSA agent your boarding pass, position it straight on the scanner yourself. Then, hold it up for inspection.
> - One liquid hand sanitizer container is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll need to take it out of your bag for scanning.
> - Place any personal items (phone, keys and wallet) in your carry-on rather than a bin to minimize handling during the screening process.
> - Separate any food you're carrying for screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to handle and inspect your belongings.

### Which airlines fly to Windley Key?

### How can I find cheap tickets to Windley Key?

### How much is a flight to Windley Key?

### What are the most popular airports to fly into in Windley Key?

### When is the cheapest time to fly to Windley Key?

### How much is a plane ticket to Windley Key?

### Which airlines with flights to Windley Key employ COVID-19 cleanliness policies?

> - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
> - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
> - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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- [North Key Largo Vacations ](https://www.expedia.ca/North-Key-Largo.d553248635976475358.Destination-Travel-Guides)
- [Plantation Key Vacations ](https://www.expedia.ca/Plantation-Key.d553248635083898347.Destination-Travel-Guides)
- [Visit Plantation Key ](https://www.expedia.ca/Plantation-Key.dx553248635083898347)
- [Prime Outlets Florida City ](https://www.expedia.ca/Prime-Outlets-Florida-City-Miami.d6127974.Vacation-Attraction)
- [Sombrero Beach ](https://www.expedia.ca/Sombrero-Beach-Marathon.d6069239.Vacation-Attraction)
- [Sunset Park Beach ](https://www.expedia.ca/Sunset-Park-Beach-Key-Colony-Beach.d553248621532652328.Vacation-Attraction)
- [Windley Key Fossil Reef Geological State Park ](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Islamorada.d6282211.Vacation-Attraction)

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- [Car rental Islamorada ](https://www.expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)
- [Convertible Car Rentals in Islamorada ](https://www.expedia.ca/Convertible-Car-Rentals-In-Islamorada.d10768-tConvertible.Car-Rental-Guide-Class)
- [Luxury Car Rentals in Islamorada ](https://www.expedia.ca/Luxury-Car-Rentals-In-Islamorada.d10768-tLuxury.Car-Rental-Guide-Class)
- [Mex Rent A Car Rental Cars in Plantation Key ](https://www.expedia.ca/Mex-Rent-A-Car-Car-Rentals-In-Plantation-Key.d553248635083898347-c1084.Car-Rental-Guide-Suppliers)
- [Pickup Car Rentals in Islamorada ](https://www.expedia.ca/Pickup-Car-Rentals-In-Islamorada.d10768-tPickup.Car-Rental-Guide-Class)
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- [Sixt Rental Cars in Islamorada ](https://www.expedia.ca/Sixt-Car-Rentals-In-Islamorada.d10768-c35.Car-Rental-Guide-Suppliers)
- [Thrifty Car Rental Rental Cars in Islamorada ](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Islamorada.d10768-c45.Car-Rental-Guide-Suppliers)

- [Islamorada Vacation Rentals ](https://www.expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)

- [Things to do in Islamorada ](https://www.expedia.ca/Things-To-Do-In-Islamorada.d10768.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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