Windley Key Vacations from $361

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The Latest Windley Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
May-Dee Suites
1 Hotel South Beach
The Retreat Collection at 1 Hotel & Homes South Beach
Cavalier Hotel South Beach
6080 Design Hotel by Eskape Collection

Windley Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

Windley Key Hotel Deals

Coconut Cove Resort and Marina
Coconut Cove Resort and Marina
2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is $151 per night from Jun 10 to Jun 11
$151
$170 total
includes taxes & fees
Jun 10 - Jun 11
7.2/10 Good! (664 reviews)
A tiny piece of paradise. No, Really.
"I had never been to the island keys. This small resort seemed to represent a little of the magic I had always imagined. It is old, dated, and in some places could use updates such as shower faucets and kitchen supplies. But overall, I found it to be very charming in a rustic island way. It is convenient. ..."

Reviewed on Jun 6, 2024

Coconut Cove Resort and Marina
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 $132 per night from Jun 24 to Jun 25
$132
$182 total
includes taxes & fees
Jun 24 - Jun 25
7.4/10 Good! (1,001 reviews)
"I stayed here for one night after leaving Sugarloaf key, to be nearer friends and also the Miami airport. It was wonderfully appointed (room), clean and totally updated. Great view with a balcony too!"

Reviewed on May 20, 2024

Fisher Inn Resort & Marina
Drop Anchor
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
The price is $138 per night from Jun 11 to Jun 12
$138
$191 total
includes taxes & fees
Jun 11 - Jun 12
8.8/10 Excellent! (1,006 reviews)
"Older hotel but so very charming and comfy. Wonderful views."

Reviewed on Jun 7, 2024

Drop Anchor
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 $361. 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.