Windley Key Vacations from ￥356,960

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Grayson Miami Downtown

The Grayson Miami Downtown

4.5 out of 5
Downtown Miami
Price was ￥423,200, price is now ￥356,960 per person
￥356,960
per person
Oct 5 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.8/10 Excellent! (1,947 reviews)
Staff was friendly, check in and check out were smooth.

Reviewed on Jul 13, 2026

Sense28 Edgewater, an AvantStay Hotel

Sense28 Edgewater, an AvantStay Hotel

4 out of 5
Midtown
Price was ￥494,723, price is now ￥410,415 per person
￥410,415
per person
Oct 5 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.8/10 Exceptional! (81 reviews)
Everything perfect! Love the rooms!

Reviewed on Jul 14, 2026

Miami International Airport Hotel

Miami International Airport Hotel

3 out of 5
Price was ￥434,164, price is now ￥366,608 per person
￥366,608
per person
Oct 5 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
7.8/10 Good! (5,517 reviews)
Ok…,,

Reviewed on Jul 13, 2026

THesis Hotel Miami Coral Gables, Curio Collection by Hilton

THesis Hotel Miami Coral Gables, Curio Collection by Hilton

4 out of 5
Price was ￥458,858, price is now ￥395,214 per person
￥395,214
per person
Oct 5 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9/10 Wonderful! (1,002 reviews)
Room was clean, breakfast good

Reviewed on Jul 9, 2026

Hotel Victor

Hotel Victor

4.5 out of 5
South Beach
Price was ￥468,606, price is now ￥407,992 per person
￥407,992
per person
Oct 5 - Oct 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
Highly recommend staying at Hotel Victor! The staff is incredible and very happy to assist with room changes, bikes, and amenities! Location is perfect for sightseeing in South Beach and very walkable!

Reviewed on Jul 13, 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 ￥41,091 per night from Aug 12 to Aug 13
￥41,091
￥58,052 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (228 reviews)
"We had a schizophrenic experience at this resort. Some elements are well done....the food is great (particularly Kindler and also The Lemon) and we encountered some supportive, friendly and helpful team members. But....the renovation attempted to tie together multiple old dingy Key's resorts into ..."

Reviewed on Jul 13, 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 ￥20,476 per night from Aug 11 to Aug 12
￥20,476
￥28,312 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"A/C was not cooling properly, parking was limited and breakfast was very limited."

Reviewed on Jul 14, 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 ￥30,558 per night from Aug 9 to Aug 10
￥30,558
￥34,378 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (274 reviews)
"Office staff was extremely friendly and helpful."

Reviewed on Jul 12, 2026

Coconut Cove Resort and Marina
See all 2,685 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.

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
See properties

Frequently asked questions

How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just ￥356,960. Choose from any combination of hotels, flights and rental cars to build the escape you've been dreaming about. Be sure to add on one or two experiences!
How do I get a cheap travel package to Windley Key?
Bundle your hotels and flights with Expedia to save big bucks on your next adventure. With more than 550 air carriers and 1,000,000 hotels across the globe, your Windley Key vacation package can be customized exactly to suit your travel style. With all that extra cash, why not include one or more exciting tours and experiences? It's an easy way to unlock even more savings. That vacation you've always dreamed of in Windley Key is closer than you thought!
How far in advance should I book my Windley Key vacation?
While prices change from time to time, we generally advise booking your flight as early as possible. Many international fares become available on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Windley Key sometimes appear just weeks before departure.
What does an Expedia Windley Key travel package include?
Expedia has everything you need to lock in Windley Key escape, but what your package looks like depends on you. Select from any combination of flights, rental cars and hotels. Looking for some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. No matter your style, there's a vacation package to meet your needs.
What should I know before booking a Windley Key travel package?
So many places to go, so many things to do. With a package, you can check more of them off your list. Bundle your flights, hotels and rental cars and see how much you save.
Can I choose my airline with a Windley Key Expedia vacation package?
With a vacation package, you're in charge. Whether you'd prefer to fly to Windley Key in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Windley Key vacation package?
It is possible to cancel your Windley Key booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Explore a world of travel with Expedia

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