Windley Key Holidays

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Top hotels in Windley Key

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 Rp4.167.298 per night from 24 Jun to 25 Jun
Rp4.167.298
Rp5.776.644 total
24 Jun - 25 Jun
includes taxes & fees
9.2/10 Wonderful! (36 reviews)
"This is a stunning property with so many amenities and restaurants! I can’t say enough about the friendliness and cooperation of the staff! Alondra at the front desk in particular! She went out of her way to accommodate our needs! Well done, Three Waters! The only complaint is that our stay wasn’t ..."

Reviewed on 17 Jun 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 Rp1.903.692 per night from 9 Jul to 10 Jul
Rp1.903.692
Rp2.676.810 total
9 Jul - 10 Jul
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Our stay was nice. Nobody cleaned our room. We had to go to the office to get towels daily. The continental breakfast has gone downhill big time since my last visit. Not enough coffee for each of us. Nothing but toast and bagels with no butter."

Reviewed on 19 Jun 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 Rp2.771.093 per night from 23 Jun to 24 Jun
Rp2.771.093
Rp3.117.480 total
23 Jun - 24 Jun
includes taxes & fees
7.6/10 Good! (794 reviews)
"Good value hotel with easy access to everything in the area."

Reviewed on 20 Jun 2025

Coconut Cove Resort and Marina
See all 2,696 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 holiday 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 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.

What to do in Windley Key

Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

Rp8.163.500
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
See all activities in Windley Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.