Windley Key Vacations from ￥306,854

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The Latest Windley Key Vacation Packages

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

President Hotel Villa

3.5 out of 5
South Beach
Price was ￥355,725, price is now ￥306,854 per person
￥306,854
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
nice location, good room. nice breakfast and evening reception

Reviewed on Feb 22, 2026

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was ￥552,419, price is now ￥422,141 per person
￥422,141
per person
Apr 9 - Apr 13
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
Clean room, excellent staff at the front desk, dining room, pool staff, and beach staff. Sergiy was especially helpful telling us all about the hotel.

Reviewed on Feb 13, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ￥367,609, price is now ￥310,166 per person
￥310,166
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on Feb 24, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥384,824, price is now ￥331,096 per person
￥331,096
per person
Apr 10 - Apr 12
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

Find the Best Windley Key Vacation Packages

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 ￥68,763 per night from Mar 22 to Mar 23
￥68,763
￥87,706 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (158 reviews)
Fun outdoor tiki bar. Beautiful beach access. Nice room.

Reviewed on Feb 27, 2026

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 ￥42,023 per night from Mar 1 to Mar 2
￥42,023
￥52,363 total
Mar 1 - Mar 2
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The room was spacious and clean with a nice view of the ocean. Unfortunately, our weeks stay was marred by the arctic freeze up and down the east coast. We were unable to access the "heated pool" nor go into the ocean. The clerk at the desk is very friendly. The pillows in our unit were dead. There ...

Reviewed on Feb 25, 2026

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 ￥55,177 per night from Mar 1 to Mar 2
￥55,177
￥62,074 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (201 reviews)
Staff are wonderful, rooms are clean and well kept, nice small resort and great atmosphere. The BYOB Tiki Bar is a real hit in my book.

Reviewed on Feb 25, 2026

Coconut Cove Resort and Marina
See all 2,741 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.

Frequently asked questions

Can I cancel my flight booking to Windley Key due to COVID-19?
Our handy Customer Service Portal has information about canceling 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 travelers 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 travelers 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 travelers 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.