
Windley Key Vacations from $618
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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.

Pelican Hotel
South Beach
Save 100% on your flight
Price was $1,140, price is now $618 per person
$618
per person
May 25 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (443 reviews)
Really enjoyed our stay at the Pelican. It’s in a great location. The staff were friendly and helpful. The room was lovely.
Costs were slightly excessive - we didn’t get the room we had booked. The resort fee was a bit disappointing as it didn’t include an umbrella at the beach (just chairs). We were also charged $75 for a crib for our 2 year old…
Reviewed on Apr 18, 2026

Casablanca Miami Beach
North Beach
Price was $2,937, price is now $1,327 per person
$1,327
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
5.8/10 (322 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026



President Hotel
South Beach
Save 100% on your flight
Price was $1,281, price is now $656 per person
$656
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
Kevin at the door was great, breakfast was good and plentiful.
Reviewed on Apr 18, 2026
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
$305 nightly
The price is $343 total per night from May 4 to May 5
$343 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (185 reviews)
We loved everthing about this resort! We just wish we had stayed longer! We stayed in The Cove. It was secluded and quiet! A perfect get away!
Reviewed on Apr 16, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $194 total per night from May 6 to May 7
$194 total
May 6 - May 7
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
Beautiful view of the ocean
Reviewed on Apr 18, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$289 nightly
The price is $325 total per night from May 18 to May 19
$325 total
May 18 - May 19
Total with taxes and fees
9/10 Wonderful! (245 reviews)
Customer service was excellent
Reviewed on Apr 18, 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.
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
- 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
- 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.



















