Windley Key Vacations

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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

84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
NT$6,637
NT$9,810 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (250 reviews)
"Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water ..."

Reviewed on 2026/8/14

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
NT$3,241
NT$4,691 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The vent cover in the bathroom ceiling was completely covered with fuzzy lint/dust."

Reviewed on 2026/8/14

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL
NT$4,773
NT$5,370 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (280 reviews)
"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"

Reviewed on 2026/8/5

Coconut Cove Resort and Marina
See all 2,715 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.
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Hog Heaven

After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area, or enjoy its fishing spots.
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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.

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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.