Windley Key Holidays from AU$3,931

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The Latest Windley Key Holiday Deals

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

The Penguin Hotel

3.5 out of 5
South Beach
Price was AU$5,780, price is now AU$3,931 per person
AU$3,931
per person
30 Dec - 6 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
My husband and I were extremely satisfied with our stay at The Penguin Hotel. We arrived mid morning and were greeted by a wonderful person at the front desk. We knew our room would not be ready that early and fully expected to have to wait until the afternoon. The person at the front desk gave us great service. She showed us where we could change, offered us storage for our luggage, gave us towels and chairs for the beach and even gave us a map of the area. She also took our phone number and said that she would call once our room was ready. She did call, and when we got back to the hotel we headed up to our room which was clean and very nice. The hotel is located right on the beach and we would recommend this hotel to anyone looking to stay on South Beach.

Reviewed on 30 Nov 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was AU$59,880, price is now AU$28,850 per person
AU$28,850
per person
30 Dec - 6 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8/10 Very Good! (1 review)
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was AU$7,356, price is now AU$4,330 per person
AU$4,330
per person
30 Dec - 6 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.4/10 Very Good! (829 reviews)
Rooms were clean and the staff were good as well.

Reviewed on 19 Nov 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was AU$8,169, price is now AU$5,315 per person
AU$5,315
per person
30 Dec - 6 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (466 reviews)
I have stayed at tgis hotel few times, it is perfect location in south beach, easy access to everything, recently the hotel did some renovations, and improvement. The staff ws great, very welcoming and helpful. The rooms are very clean and the room i stayed in was great and had partial ocean view, the hotel has variety of room options. Roof top swming pool was nice, and the beach was too minutes walk. Overall, great stay and nice hotel

Reviewed on 28 Nov 2025

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was AU$5,961, price is now AU$4,008 per person
AU$4,008
per person
30 Dec - 6 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Helpful staff , good location

Reviewed on 27 Nov 2025

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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$465 per night from 14 Dec to 15 Dec
AU$465
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (112 reviews)
Beautiful room, stunning views

Reviewed on 19 Nov 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$194 per night from 18 Dec to 19 Dec
AU$194
18 Dec - 19 Dec
includes taxes & fees
8/10 Very Good! (1,012 reviews)
Room spotless excelent staff. This is a great place.

Reviewed on 25 Nov 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$221 per night from 1 Dec to 2 Dec
AU$221
1 Dec - 2 Dec
includes taxes & fees
9/10 Wonderful! (141 reviews)
Quiet and relaxing. Great place

Reviewed on 18 Nov 2025

Coconut Cove Resort and Marina
See all 2,783 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.