Windley Key Holidays

Book a Hotel + Flight or Car together to unlock savings

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 4.654.430 ₫ per night from 19 Aug to 20 Aug
4.654.430 ₫
6.975.389 ₫ total
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (52 reviews)
Three Waters is a beautiful place to vacation.
"Three Waters Resort was wonderful. We stayed in the Cove and it was very relaxing. The accommodations were spacious and clean."

Reviewed on 27 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 refundable
The price is 2.688.120 ₫ per night from 12 Aug to 13 Aug
2.688.120 ₫
3.879.042 ₫ total
12 Aug - 13 Aug
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"The property was prestine with a nice pool overlooking the water and a beautiful beach. I like the music they played on speaker in the recreational areas. They have dim lights at night the reflect on the water..so relaxing. The staff was excellent and manager, Thomas, was outstanding."

Reviewed on 27 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 4.220.820 ₫ per night from 4 Aug to 5 Aug
4.220.820 ₫
4.748.422 ₫ total
4 Aug - 5 Aug
includes taxes & fees
7.6/10 Good! (808 reviews)
"Really liked the property and staff was very informative and kind. Also love the 24 hour pool access!"

Reviewed on 27 Jul 2025

Coconut Cove Resort and Marina
See all 2,759 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.

Popular places to visit

Windley Key Fossil Reef Geological State Park

Windley Key Fossil Reef Geological State Park

Explore the great outdoors at Windley Key Fossil Reef Geological State Park and enjoy the beautiful sunsets during your trip to Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.

Windley Key Fossil Reef Geological State Park

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 1null000null000 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.