Windley Key Vacations from ￥430,963

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
EAST Miami

EAST Miami

5 out of 5
Brickell
Price was ￥661,982, price is now ￥430,963 per person
￥430,963
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to Miami (MIA)
9.2/10 Wonderful! (3,553 reviews)
Everything was great fresh breakfast great view from the balcony

Reviewed on Nov 22, 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was ￥831,016, price is now ￥485,478 per person
￥485,478
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.4/10 Very Good! (829 reviews)
Rooms were clean and the staff were good as well.

Reviewed on Nov 19, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
Price was ￥972,099, price is now ￥598,703 per person
￥598,703
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.2/10 Wonderful! (466 reviews)
Everything was gorgeous and extremely comfortable! Check in was smooth and friendly! Thank you!

Reviewed on Nov 26, 2025

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was ￥712,884, price is now ￥466,294 per person
￥466,294
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
The location is good, decent room. Service can be better

Reviewed on Nov 26, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was ￥665,440, price is now ￥435,412 per person
￥435,412
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.2/10 Wonderful! (172 reviews)
The amenities were great. The balcony and the balcony view made every penny worth it - on top of that, the fully stocked kitchen and super comfy living space were relaxing. It would be cool if there was a tv in the bedroom, though…

Reviewed on Nov 9, 2025

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 ￥31,724 per night from Dec 9 to Dec 10
￥31,724
￥46,055 total
Dec 9 - Dec 10
includes taxes & fees
8.8/10 Excellent! (112 reviews)
Beautiful room, stunning views

Reviewed on Nov 19, 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 ￥13,100 per night from Dec 18 to Dec 19
￥13,100
￥19,836 total
Dec 18 - Dec 19
includes taxes & fees
8/10 Very Good! (1,013 reviews)
Clean quiet

Reviewed on Nov 26, 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 ￥16,689 per night from Nov 30 to Dec 1
￥16,689
￥18,775 total
Nov 30 - Dec 1
includes taxes & fees
9/10 Wonderful! (141 reviews)
Quiet and relaxing. Great place

Reviewed on Nov 18, 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.

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.

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