Windley Key Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Windley Key

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

Hotel Ocean

3.5 out of 5
South Beach
Price was €968, price is now €682 per person
€682
per person
29 Dec - 1 Jan
found 6 hours ago
Return flight included
Chicago (ORD) to Miami (MIA)
7.6/10 Good! (1,002 reviews)
Convenience, friendly staff.

Reviewed on 17 Sept 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was €1,575, price is now €993 per person
€993
per person
29 Dec - 1 Jan
found 6 hours ago
Return flight included
Chicago (ORD) to Miami (MIA)
8.6/10 Excellent! (116 reviews)
Cllean room, good food, prices high

Reviewed on 8 Oct 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was €1,524, price is now €965 per person
€965
per person
29 Dec - 1 Jan
found 6 hours ago
Return flight included
Chicago (ORD) to Miami (MIA)
9.2/10 Wonderful! (334 reviews)
Not much of a beach view

Reviewed on 7 Oct 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Price was €1,741, price is now €1,130 per person
€1,130
per person
29 Dec - 1 Jan
found 6 hours ago
Return flight included
Chicago (ORD) to Miami (MIA)
9.2/10 Wonderful! (3,369 reviews)
Struggled finding any pet potty areas anywhere nearby. I kept having to load into my SUV and take several blocks up to biscayne, margaret pace park. It took away from the experience for sure.it was a lot

Reviewed on 7 Oct 2025

Miami Design District - Condos

Miami Design District - Condos

5 out of 5
Northeast Miami
Price was €1,001, price is now €708 per person
€708
per person
29 Dec - 1 Jan
found 6 hours ago
Return flight included
Chicago (ORD) to Miami (MIA)
No reviews

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is €235 per night from 15 Oct to 16 Oct
€235
15 Oct - 16 Oct
includes taxes & fees
8.8/10 Excellent! (91 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 refundableReserve now, pay when you stay
The price is €131 per night from 2 Nov to 3 Nov
€131
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (1,000 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 €129 per night from 12 Oct to 13 Oct
€129
12 Oct - 13 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 2,761 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

€427
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!
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.

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