
Windley Key Vacations from $638
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.

Beach House Fort Lauderdale, a Hilton Resort
East Fort Lauderdale
Price was $1,202, price is now $638 per person
$638
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (2,331 reviews)
Stayed for a quick girls weekend and the property beautiful with a friendly/welcoming staff. The location was great as we had lots of great food options within walkable distance. However, our floor was under construction/ maintenance so it wasn't the cleanest. We were at the end of the hallway and in the corners you can see an accumulation of dust/dirt. The shower was surprisingly small for the size of the bathroom and didn't have a seal on the door so at the end of your shower you would be stepping on a wet mat. Also, by 10/10:30am there were not enough umbrellas on the beach or anywhere to lay down by the pool except for the cabanas.
Reviewed on Apr 21, 2026

Casablanca Miami Beach
North Beach
Price was $2,891, price is now $1,311 per person
$1,311
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip 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 $1,557, price is now $819 per person
$819
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,231 reviews)
Breakfast was good, everyone friendly and lets us store bags before our room was ready
Reviewed on Apr 22, 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
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $352 total per night from May 4 to May 5
$352 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (187 reviews)
They hit you with a $65 per day resort fee…. Not the end of the world but not a good surprise after you leave.
Reviewed on Apr 21, 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! (1,009 reviews)
Amazing hotel
Reviewed on Apr 20, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night from Apr 23 to Apr 24
$201 total
Apr 23 - Apr 24
Total with taxes and fees
9/10 Wonderful! (248 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.



















