Windley Key Holidays from AU$952

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The Latest Windley Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was AU$1,450, price is now AU$952 per person
AU$952
per person
17 Dec - 21 Dec
found 15 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
The staff greeted us wonderfully. The room is clean. The VIP perk was pleasant. Would definitely stay here again.

Reviewed on 25 Sept 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was AU$1,616, price is now AU$1,046 per person
AU$1,046
per person
17 Dec - 21 Dec
found 15 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
Super cute! Very friendly check in and bar. Everything you could need is walkable. I wish we were staying longer, but we only have 1 night before a cruise. Very convenient to the port.

Reviewed on 9 Oct 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was AU$1,472, price is now AU$980 per person
AU$980
per person
17 Dec - 21 Dec
found 15 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.2/10 Very Good! (1,440 reviews)
Right on the beach, very vibrant area! Would stay here again.

Reviewed on 8 Oct 2025

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was AU$2,126, price is now AU$1,421 per person
AU$1,421
per person
17 Dec - 21 Dec
found 15 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (2,936 reviews)
Great resort! Great location. Multiple pools. Clean rooms, beautiful property. Staff always treats me so well. The concierge Joao really went above and beyond for me. He really made my trip special. Check in went very smoothly as well. Highly recommended!

Reviewed on 8 Oct 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was AU$2,058, price is now AU$1,377 per person
AU$1,377
per person
17 Dec - 21 Dec
found 15 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8/10 Very Good! (1,102 reviews)
The one thing that I have to mention about this hotel is their water pressure. Almost all hotels have little water flow and little pressure. It is normal, but this only hotel got the biggest water flow. It was amazing to take a shower that was more comfortable than own home. I have never seen a hotel with the water flow. It was so comfortable

Reviewed on 4 Oct 2025

Windley Key Holiday

Windley Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Top Sights
Windley Key Fossil Reef Geological State Park and Windley Key Fossil Reef Geological State Park

Our pick of the best Windley Key Hotel Deals

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

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$419 per night from 15 Oct to 16 Oct
AU$419
15 Oct - 16 Oct
includes taxes & fees
8.8/10 Excellent! (92 reviews)
"Truly enjoyed our visit to this property. Lots to do and great dining options! We will be back."

Reviewed on 29 Sept 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
Fully refundable
The price is AU$231 per night from 2 Nov to 3 Nov
AU$231
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (999 reviews)
Great view
"Two night stay . Advertised paddle boards and kayaks but although front desk employee was nice she didn’t get up or go out of her way to offer much additional info on anything. Never saw the kayaks or paddle boards and wasn’t an actual beach right there so no clue where you go to do that. Heard another ..."

Reviewed on 16 Sept 2025

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway, Islamorada, FL
The price is AU$208 per night from 14 Oct to 15 Oct
AU$208
14 Oct - 15 Oct
includes taxes & fees
7.6/10 Good! (822 reviews)
"Staff make you feel very welcome Old skool Florida hotel."

Reviewed on 3 Oct 2025

Coconut Cove Resort and Marina
See all 2,755 properties in Windley Key
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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Frequently asked questions

Can I cancel my flight booking to Windley Key due to COVID-19?
Our handy Customer Service Portal has information about cancelling your Windley Key flight due to COVID-19. Before booking your tickets, it's smart to check the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Windley Key that have flexible change policies?
We get that travel schedules can change in a flash, so locking in a flexible ticket with Expedia is always a smart move. Just tick the "No change fee" box directly below the "Flexible change policies" filter. Your well-priced and flexible flight to Windley Key is only a few clicks away.
What are some of the general tips for travellers to Windley Key during the COVID-19 outbreak?
With strict COVID-19 precautions to adhere to, travel looks a lot different at the moment. These are some helpful things to know before you pack your bags for Windley Key:
  • 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?
Book your fare with Delta and then begin planning your Windley Key itinerary. This leading airline provides 191 flights per month to Key West Intl. Airport (EYW), a central gateway.
How can I find cheap tickets to Windley Key?
You'll always find a fabulous deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then tick the flexible dates box above to reveal the cheapest prices for nearby days. was the best price for a flight to Windley Key in the last seven days.
How much is a flight to Windley Key?
You could have locked in a return air ticket to Windley Key from anywhere between and in the last seven days. For one-way journeys from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Windley Key?
The primary gateway to Windley Key, around 1119 flights taxi into Key West Intl. Airport (EYW) each month. Find a top deal, book your ticket and get ready to enjoy the best of this fantastic region.
When is the cheapest time to fly to Windley Key?
Try to jet off early on in the week to book a bargain airfare to Windley Key. Tuesday is routinely the most affordable day to depart, followed by Monday. Saturday typically has the highest prices. This is because lots of travellers like to begin their getaway on a weekend.
How much is a plane ticket to Windley Key?
In the last seven days, fares cost between and . Browse through our fantastic deals to Windley Key, make a booking and then get ready for your getaway!
Which airlines with flights to Windley Key employ COVID-19 cleanliness policies?
To help minimize contact between travellers and cabin crew during the ongoing pandemic, airlines have taken physical distancing and other precautionary measures to the skies. Just some of these are:
  • 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.