
Windley Key Vacations from $753
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

President Hotel
South Beach
Save 100% on your flight
Price was $1,417, price is now $753 per person
$753
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,251 reviews)
It looks like it was renovated recently the rooms are nice. Breakfast was good and access to beach was great. The staffs are friendly and helpful. I like they keep your luggages for free after check out.
Reviewed on Apr 23, 2026

Casablanca Miami Beach
North Beach
Price was $2,879, price is now $1,328 per person
$1,328
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


Creekside Inn
Save 100% on your flight
Price was $1,552, price is now $809 per person
$809
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,011 reviews)
Check-in was easy and welcoming. Easy parking. Room was very clean. Plenty of towels and toiletries. We had a lower level room on the canal. It was private and quiet. There was a table and chairs that allowed us the opportunity to sit outside in the evening. We had a pleasant stay.
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
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
$330 nightly
The price is $371 total per night from May 4 to May 5
$371 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (188 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! (1,002 reviews)
Great location for a fishing trip to the keys with my son. It was super continently located and the room was fresh and I’d recommend.
Reviewed on Apr 22, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$179 nightly
The price is $201 total per night from Apr 26 to Apr 27
$201 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (249 reviews)
It was an older resort with lots of room to spread out. Personal, attentive staff. Facility was clean, you can see they are working to revitalize the resort. Nice place, great location.
Reviewed on Apr 22, 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) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















