Windley Key Vacations from $350
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Stayed here for one night with my wife and we loved our stay. Would definitely be coming back
Reviewed on Jul 28, 2025
Casablanca Miami Beach
North Beach
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
5.8/10 (303 reviews)
It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.
Reviewed on Jun 21, 2025
Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all tripsDiscover the most popular places to visit in Windley Key
Windley Key Fossil Reef Geological State Park
4.5/5(20 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.
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
$237 nightly
The price is $266 total per night from Aug 19 to Aug 20
$266 total
Aug 19 - Aug 20
Total includes taxes and 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 Jul 27, 2025
Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $161 total per night from Aug 11 to Aug 12
$161 total
Aug 11 - Aug 12
Total includes taxes and 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 Jul 27, 2025
Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$159 nightly
The price is $179 total per night from Aug 18 to Aug 19
$179 total
Aug 18 - Aug 19
Total includes taxes and fees
7.6/10 Good! (806 reviews)
"Really liked the property and staff was very informative and kind. Also love the 24 hour pool access!"
Reviewed on Jul 27, 2025
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.
Find the Best Windley Key Vacation Packages
Windley Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
More vacations you might like
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Hotels near Venetian Shores
- Islamorada Hotels
- Hotels near Windley Key Fossil Reef Geological State Park
- Hotels near Islamorada County Park
- Hotels near Founders Park
- Hotels near History of Diving Museum
- Plantation Key Hotels
- Oceanfront Hotels in Plantation Key
- Resorts in Islamorada
- Cheap Hotels in Islamorada
- Oceanfront Hotels in Islamorada
- All-inclusive Resorts in Islamorada
- Pet-friendly Hotels in Islamorada
- Beach Hotels in Islamorada
- Luxury Hotels in Islamorada
- Adults Only Resorts & in Islamorada
- Hilton Hotels in Islamorada
- Marriott Hotels & Resorts in Islamorada
- Houseboats in Islamorada
- Cottages in Islamorada
- Family Hotels in Islamorada
- Motels in Islamorada
- Hotels with a Swim-up Bar in Islamorada
- Hotels with Bars in Islamorada
- Fishing Resorts & in Islamorada
- Condo Rentals in Islamorada
- Boutique Hotels in Islamorada
- Wyndham Hotels in Islamorada
- Honeymoon Resorts & in Islamorada
- 5 Star Hotels in Islamorada
- Villas in Islamorada
- Hotels with Free Breakfast in Islamorada
- Resorts & Hotels with Spas in Islamorada
- RV Parks in Islamorada
- Hotels with Restaurants in Islamorada
- Hotel Wedding Venues Hotels in Islamorada
- Romantic Hotels in Islamorada
- Vacation Homes in Islamorada
- 4 Star Hotels in Islamorada
- Gay friendly Hotels in Islamorada
- Apartments in Islamorada
- Hotels with Kitchenettes in Islamorada
- Hotels with Suites in Islamorada
- Hotels with Hot Tubs in Islamorada
- Hotels with Laundry Facilities in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Historic Hotels in Islamorada
- Treehouses in Islamorada
- Golf Hotels in Islamorada
- Guest Houses in Islamorada
- Hotels with a Gym in Islamorada
- Hotels & Resorts for Couples in Islamorada
- 3 Star Hotels in Islamorada
- B&B in Islamorada
- Hersha Hospitality Hotels in Islamorada
- Hotels with smoking rooms in Islamorada
- Hotels with Room Service in Islamorada
- Aimbridge Hospitality Hotels in Islamorada
- Hotels with Tennis Courts in Islamorada
- Hotels with a Pool in Islamorada
- Best Western Hotels in Islamorada
- Hotels with Childcare in Islamorada
- Lodges in Islamorada
- Rainforest & Jungle Hotels in Islamorada
- Quiet Resorts & in Islamorada
- Hotels with a View in Islamorada
- Hotels with Balconies in Islamorada
- Hotels with an Outdoor Pool in Islamorada
- Hotels with Free Parking in Islamorada
- Aparthotels in Islamorada
- Flights from Plantation Key
- Flights to Islamorada
- Flights from Islamorada
- Flights from Tampa to Islamorada
- Flights from New York to Islamorada
- Flights from Cleveland to Islamorada
- Flights from Kansas City to Islamorada
- Flights from Columbus to Islamorada
- Flights from Boston to Islamorada
- Flights from Atlanta to Islamorada
- Flights from Baltimore to Islamorada
- Flights from Minneapolis - St. Paul to Islamorada
- Car rentals near Islamorada
- Hertz Rental Cars in Islamorada
- Enterprise Rental Cars in Islamorada
- Thrifty Car Rental Rental Cars in Islamorada
- Budget Rental Cars in Islamorada
- Van Car Rentals in Islamorada
- Avis Rental Cars in Islamorada
- Alamo Rent A Car Rental Cars in Islamorada
- Luxury Car Rentals in Islamorada
- National Car Rental Rental Cars in Islamorada
- Convertible Car Rentals in Islamorada
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.