Windley Key Vacations from ￥228,036

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
Friendly staff. Beautiful room with a view. Great pool and restaurants.

Reviewed on Jul 29, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Beautiful rooms drinks on the high end

Reviewed on Jul 31, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Lots of outside noise throughout the night and hallway was very loud too

Reviewed on Jul 30, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Always a fun time, hotel rooms need a little bit of a refresh. Becoming a tad bit outdated.

Reviewed on Jul 31, 2025

Trump International Beach Resort

Trump International Beach Resort

4.5 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Miami (MIA)
8.2/10 Very Good! (4,244 reviews)
Great vacation spot and close to everything South beach. , Brickell and. Hard rock Casino 20-30 mins. Ratio. Depending on traffic

Reviewed on Jul 28, 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 ￥26,530 per night from Aug 19 to Aug 20
￥26,530
￥39,759 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (52 reviews)
Three Waters is a beautiful place to vacation.
"Three Waters Resort was wonderful. We stayed in the Cove and it was very relaxing. The accommodations were spacious and clean."

Reviewed on Jul 27, 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 ￥14,466 per night from Aug 13 to Aug 14
￥14,466
￥21,119 total
Aug 13 - Aug 14
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"The property was prestine with a nice pool overlooking the water and a beautiful beach. I like the music they played on speaker in the recreational areas. They have dim lights at night the reflect on the water..so relaxing. The staff was excellent and manager, Thomas, was outstanding."

Reviewed on Jul 27, 2025

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is ￥21,529 per night from Aug 13 to Aug 14
￥21,529
￥24,220 total
Aug 13 - Aug 14
includes taxes & fees
7.6/10 Good! (809 reviews)
Very Relaxing
"Beautiful setting with nice pool as well! The staff is very friendly and helpful, especially Clancy!!"

Reviewed on Jul 30, 2025

Coconut Cove Resort and Marina
See all 2,716 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

How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just ￥228,036. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.