Windley Key Vacation Packages
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Top Windley Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $15,276
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Viscay Hotel
South Beach
CA $2,591
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand
Reviewed on Jul 16, 2026
Pantera Rosa
South Beach
CA $1,296
per person
Sep 19 - Sep 26
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (74 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.
Reviewed on Jun 26, 2026
Ready to book your vacation to Windley Key?
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
CA $289
CA $427 total
Aug 17 - Aug 18
includes taxes & fees
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $149
CA $213 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very good! (1,012 reviews)
"Never got the water hot in the shower."
Reviewed on Aug 8, 2026
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
CA $208
CA $234 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (279 reviews)
"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"
Reviewed on Aug 5, 2026
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 CA $683. 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
- Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
- Wynken Blynken and Nod Hotels
- Oceanfront Hotels in Islamorada
- Keys Waterfront Condo
- Hotels near Baker's Cay Resort Beach
- Best Western Hotels in Key Largo
- Pineapple Beach by Florida Keys Luxury Rentals
- Hotels near Everglades National Park
- Amoray Dive Resort
- B&B in Tavernier
- All Inclusive Resorts and in Key Largo
- Islamorada Hotels
- Wyndham Hotels in Islamorada
- Tropical Escape
- Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
- Cottages in Islamorada
- Tavernier Hotels
- Family Hotels in Key Largo
- La Siesta Resort & Villas
- Hotels with smoking rooms in Islamorada
- Luxury Hotels in Islamorada
- Stunning Direct Ocean Views from 2BR Suite
- Cheap Hotels in Islamorada
- Waterfront Home With Swimming Pool
- Family Hotels in Islamorada
- Condo Rentals in Key Largo
- Hotels with Waterslides in Islamorada
- Matecumbe Hotels
- Boutique Hotels in Islamorada
- Beach Hotel Hotels in Islamorada
- Bayside Villas by Islander Resort
- Hersha Hospitality Hotels in Upper Matecumbe Key
- Inns in Islamorada
- Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex
- Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
- Rv Parks in Lignumvitae Key Botanical State Park
- Direct Oceanfront Corner Condo
- Resorts in Upper Matecumbe Key
- Houseboats in Windley Key
- Cheap Hotels in Key Largo
- Motels in Islamorada
- Oceanfront Hotels in Key Largo
- Key Largo Hotels
- Fish
- Luxury Hotels in Key Largo
- All Inclusive Resorts and in Islamorada
- Hotels with Free Airport Shuttle in Islamorada
- Beach Hotel Hotels in Key Largo
- Rv Parks in Lower Matecumbe Key
- Barefoot Bliss
- Adults Only Resorts & in Key Largo
- Visit Key Largo
- Shark Valley Observatory Tower
- Biscayne National Park
- Ernest F. Coe Visitor Center
- Everglades National Park
- Visit Seabreeze Trailer Park
- Crane Point Museum and Nature Center
- Miccosukee Casino
- Key Largo Vacations
- Coconut Grove Vacations
- Veterans Memorial Park & Beach
- Bill Baggs Cape Florida State Park
- Visit Upper Matecumbe Key
- Dagny Johnson Key Largo Hammock Botanical State Park
- Calusa Beach
- Florida City Vacations
- Sunset Park Beach
- Visit Plantation Key
- Zoo Miami
- Shark Valley Visitor Center
- Baker's Cay Resort Beach
- Visit Islamorada
- Seven Mile Bridge
- Sombrero Beach
- Marathon Vacations
- Old Cutler Trail
- History of Diving Museum
- Islamorada Vacations
- Anne's Beach
- South Miami Vacations
- Visit Lower Matecumbe Key
- Curry Hammock State Park
- Prime Outlets Florida City
- Coral Castle Museum
- Homestead Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
