Windley Key Holidays

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Top hotels in Windley Key

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

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is Rp6.172.795 per night from 21 Apr to 22 Apr
Rp6.172.795
Rp8.068.076 total
21 Apr - 22 Apr
includes taxes & fees
9/10 Wonderful! (173 reviews)
The ocean was visible from our room and it was a beautiful resort. The staff was friendly and there was a lot to do for families.

Reviewed on 20 Mar 2026

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

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
The price is Rp6.584.992 per night from 23 Mar to 24 Mar
Rp6.584.992
Rp7.408.116 total
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (220 reviews)
Authentic old Florida, beautiful property neat and clean and very friendly. Really enjoyed the cats and chickens and the beach and view. Lovely breakfast and hot coffee each morning. Great staff. My guy loved the fitness room and the huge assortment of weights! Can't wait to return for a longer ...

Reviewed on 21 Mar 2026

Coconut Cove Resort and Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is Rp3.641.213 per night from 20 Apr to 21 Apr
Rp3.641.213
Rp4.648.726 total
20 Apr - 21 Apr
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
The pictures are very deceiving, and when they say “grab and go” breakfast, good luck grabbing anything. Coffee was always empty, bananas were mush and you were lucky if you got there early enough to get a bagel. Someone opened the door to our room, and when they figured out we were there, slammed ...

Reviewed on 20 Mar 2026

Fisher Inn Resort & Marina
See all 2,750 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.

What to do in Windley Key

Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

Rp8.479.000
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
See all activities in Windley Key

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!
What months are the cheapest to book a flight to Windley Key?
February is the best month to purchase a seat for your Windley Key holiday. Fares are at a premium during the month of December, so steer clear of this time if possible.
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.

How long is a flight to Windley Key?
It could take you an hour or two or more — it depends on which part of the USA you're taking off from. The average flight times for these leading domestic routes to Windley Key will give you a clearer idea of what to expect:
  • Atlanta, GA Airport (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 1 hour and 50 minutes
  • Charlotte, NC Airport (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 2 hours and 8 minutes
  • Miami, FL Airport (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 55 minutes

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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.