Windley Key Holidays from NZ$2,870

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    Save up to NZ$616 when you book a flight and hotel together*
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The Latest Windley Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
B Ocean Resort Fort Lauderdale Beach
Pelican Grand Beach Resort - A Noble House Resort
Eden Roc Miami Beach
Trump National Doral Miami
Gale South Beach, Curio Collection by Hilton

Windley Key Holiday

Our pick of the best 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 NZ$622 per night from 11 Aug to 12 Aug
NZ$622
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (47 reviews)
Great, but eat off property
"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."

Reviewed on 2 Jul. 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 refundableReserve now, pay when you stay
The price is NZ$269 per night from 23 July to 24 July
NZ$269
23 July - 24 July
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Enjoyed the stay but a little noisy from either the thin walls or the adjoining door made for a rough night of sleep when your neighbor is drunk and throwing up all night and yelling at his wife. Could hear everything. Only other complaint was the bed was not the most comfortable but everything else ..."

Reviewed on 11 Jul. 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 NZ$261 per night from 17 July to 18 July
NZ$261
17 July - 18 July
includes taxes & fees
7.6/10 Good! (802 reviews)
Serenity
"I took my girlfriend For a couples getaway and we both were So delighted With the incredible room, bed was amazing. The Jacuzzi tub was awesome, but the owners of the property made it so they made you feel like you were part of the family come and go please in the grounds in the pool. We're just ..."

Reviewed on 11 Jul. 2025

Coconut Cove Resort and Marina
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.

Discover the most popular places to visit in Windley Key

What to do in Windley Key

Frequently asked questions

How much does a Windley Key holiday package cost?
Custom make your Windley Key package from just NZ$2,870. 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 holiday 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 holiday you've always dreamed of in Windley Key is closer than you thought!
How far in advance should I book my Windley Key holiday?
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 holiday 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 holiday package?
With a holiday 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 holiday 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.