Windley Key Vacations from ￥78,362
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Plunge Beach Resort
￥94,550
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Miami (MIA)
8.8/10 Excellent! (1,519 reviews)
Me gustó la atención del señor Julio de la recepción nos encantó porque nos enseñó todo el funcionamiento del establecimiento fue un trato excelente gracias 👏👏
Reviewed on Aug 27, 2026
Find the Best Windley Key Vacation Packages
Windley Key Hotel Deals
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
￥27,904
￥43,038 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (255 reviews)
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Reviewed on Aug 23, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
￥18,491
￥25,999 total
Sep 21 - Sep 22
includes taxes & fees
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
￥22,083
￥24,843 total
Sep 28 - Sep 29
includes taxes & fees
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.
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.
Frequently asked questions
How much does a Windley Key vacation package cost?
Custom make your Windley Key package from just ￥78,362. 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.
Explore a world of travel with Expedia
- Aparthotels in North Key Largo
- Shopping Hotels in Key Largo
- Family Hotels in Islamorada
- Rv Parks in Florida City
- Inns in Princeton
- Motels in Islamorada
- Hotels near Prime Outlets Florida City
- Resorts in Key Largo
- Beach Hotels in Key Largo
- Hotels with a Pool in Flamingo
- Luxury Hotels in Homestead
- Resorts in No Name Key
- Condo Resorts in Key Colony Beach
- Hotels near Homestead Miami Speedway
- The Hammocks Hotels
- Hotels near Zoo Miami
- Palaces in Key Colony Beach
- Hotels near Baker's Cay Resort Beach
- Resorts in Homestead
- Key Largo Hotels
- Cheap Hotels in Key Largo
- Cheap Hotels in North Key Largo
- Hotels near Everglades National Park
- Hotels near Ocean Reef Club
- Inns in Islamorada
- Resorts in Flamingo
- Rv Parks in Long Key
- Resorts in Key Colony Beach
- Beach Hotels in Key Largo Village
- Aparthotels in Key Colony Beach
- Scuba Diving Hotels in Key Largo
- Hotels near Sombrero Beach
- Cruise Ships in Florida City
- All-Inclusive Hotel Hotels in Key Largo Village
- Hotels near Caribbean Club Bar
- Luxury Hotels in Key Largo Park
- Rv Parks in Flamingo
- Cutler Bay Hotels
- Rv Parks in Islamorada
- Family Hotels in Grassy Key
- Motels in Homestead
- Resorts & Hotels with Spas in Flamingo
- Hotels near Anne's Beach
- Hotels near Jimmy Johnson's Big Chill
- Scuba Diving Hotels in Key Largo Park
- Vacation Homes in Key Largo
- Riads in Key Largo
- Motels in Florida City
- Resorts in Duck Key
- Hotels near Homestead Air Force Base
- All-Inclusive Hotel Hotels in Key Colony Beach
- Luxury Hotels in Key Largo Village
- Beach Hotels in Key Colony Beach
- Riads in Islamorada
- Lodges in Homestead
- Adults Only Resorts & in Marathon
- Inns in Duck Key
- Cheap Hotels in Naranja
- Vacation Homes in Marathon
- Coral Lagoon Hotels
- Flamingo Hotels
- Hotels near Homestead Air Reserve Base
- Lodges in North Key Largo
- Scuba Diving Hotels in Florida City
- Islamorada Hotels
- Waterpark Hotels in Flamingo
- All-Inclusive Hotel Hotels in Key Largo
- Hostels in Flamingo
- Scuba Diving Hotels in Blue Waters
- Apartments in Homestead
- Rv Parks in Bahia Honda Key
- Resorts in Islamorada
- Cheap Hotels in Homestead
- All-Inclusive Hotel Hotels in Key Largo Park
- All-Inclusive Hotel Hotels in Matecumbe
- Guest Houses in Islamorada
- Scuba Diving Hotels in Marathon
- Resorts in Bahia Honda Key
- Marathon Hotels
- Princeton Hotels
- Hotels near Florida Keys Marathon
- Pet-Friendly Hotels in Flamingo
- All-Inclusive Hotel Hotels in Florida City
- Beach Hotels in Key Largo Park
- Cheap Hotels in Florida City
- Hotels near Biscayne National Park
- Hostels in Key Largo
- Scuba Diving Hotels in Key Largo Village
- Hotels near Calusa Beach
- Adults Only Resorts & in Long Key
- Holiday Park Resorts in Key Largo
- Hotels near Miami Executive
- Inns in Key Colony Beach
- Farmstay in Marathon
- Homestead Hotels
- Waterpark Hotels in Florida City
- Long Key Hotels
- Luxury Hotels in Key Largo
- Hotels near Biscayne Bay
- Adventure Hotels in Key Largo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
