Windley Key Vacations from ￥381,616

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kimpton Surfcomber Hotel by IHG

Kimpton Surfcomber Hotel by IHG

4.5 out of 5
South Beach
Price was ￥440,208, price is now ￥381,616 per person
￥381,616
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Miami (MIA)
8.2/10 Very Good! (1,005 reviews)
The staff and hotel was great!

Reviewed on May 29, 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was ￥806,346, price is now ￥586,014 per person
￥586,014
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Miami (MIA)
9.4/10 Exceptional! (1,512 reviews)
Phenomenal stay for me and my girlfriend. The hotel is very peaceful, refined and elegant in every way. The staff was very accommodating with all of our needs. Will be my new go to hotel in Miami from now on!

Reviewed on May 29, 2026

Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was ￥550,586, price is now ￥433,226 per person
￥433,226
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Miami (MIA)
8.6/10 Excellent! (1,377 reviews)
My stay at Nobu Miami was a fantastic experience. Not only were the amenities fantastic but the service was extraordinary. I would recommend Nobu to anyone that would like a great stay on a beautiful stretch of Miami Beach. :-)

Reviewed on May 28, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥541,306, price is now ￥427,476 per person
￥427,476
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Miami (MIA)
8/10 Very Good! (1,150 reviews)
It’s three star amenities and a three star approach to customer care

Reviewed on May 28, 2026

The Moore Miami

The Moore Miami

4 out of 5
Price was ￥593,338, price is now ￥518,584 per person
￥518,584
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Miami (MIA)
9.8/10 Exceptional! (36 reviews)
The entire staff at the Moore was fantastic, very accommodating, made sure they went out of their way for my stay. The valet area is a little inconvenient. Concierge service provider was outstanding, especially Marina. We are already planning to come back in the coming months. The area of the design district couldn’t be any better. The food was Michelin star status and above. I rate The Moore at 5⭐️

Reviewed on May 24, 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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ￥48,595 per night from Jun 14 to Jun 15
￥48,595
￥66,315 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (201 reviews)
"Very nice resort, spread out but easy to navigate, could usually flag down a golf cart if you needed to, good food choices. Plenty of amenities, rentals etc. The Cove over 21, we had a great view,balcony was small but had comfortable chairs, pools and beaches were all great spots."

Reviewed on May 29, 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 ￥22,789 per night from Jun 14 to Jun 15
￥22,789
￥30,833 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The only problem I had was , when my husband and I were laying out on the lounge chairs by the beautiful peaceful ocean , there workers were going around with those noisy blowers to push the leaves around, in the middle of the afternoon, instead of just using a rake would have made more since"

Reviewed on May 28, 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 ￥33,283 per night from Jun 21 to Jun 22
￥33,283
￥37,444 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (265 reviews)
"The property was very beautiful and the staff was great. They have an ice machine on site and a large pool area. The tiki bar is a great spot in the evening to sit and have a drink"

Reviewed on May 25, 2026

Coconut Cove Resort and Marina
See all 2,744 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.