Windley Key Vacations

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    Save up to ￥45,448 when you book a flight and hotel together*
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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 ￥28,602 per night from Sep 2 to Sep 3
￥28,602
￥41,931 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (65 reviews)
"We were only there a couple of days but we had a great time! It's typical Key West layed back vibe!"

Reviewed on Aug 26, 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 ￥14,492 per night from Sep 14 to Sep 15
￥14,492
￥21,125 total
Sep 14 - Sep 15
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Great views manatees cruising by very relaxing"

Reviewed on Aug 23, 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 ￥16,819 per night from Aug 28 to Aug 29
￥16,819
￥18,921 total
Aug 28 - Aug 29
includes taxes & fees
7.6/10 Good! (815 reviews)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again"

Reviewed on Aug 15, 2025

Coconut Cove Resort and Marina
See all 2,719 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 . 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.