
Windley Key Vacations from $358
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

The Penguin Hotel
South Beach
Save 100% on your flight  
Price was $714, price is now $358 per person
$358
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Stayed at the Penguin for the first time and had a great experience. The room was clean and comfortable. Staff was courteous and helpful upon arrival. Would recommend this property and would stay here in the future
Reviewed on Oct 31, 2025

Cavalier Hotel South Beach
South Beach
Price was $799, price is now $380 per person
$380
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
We had a great stay at the Cavalier Hotel. The interior of the hotel is beautiful. They also have a bar area as well as breakfast, lunch, and dinner options for dine-in or take-out. The beach is only a few steps away! The hotel provided beach towels as well.
Our room was clean and beds were comfortable. The bathroom doesn't have a proper door that locks. It's only a sliding door, which we found difficult for privacy. 
All the staff we met were also very friendly and helpful. 
The only note for anyone looking to stay at this property is that the hotel itself doesn't have any parking. There is a Municipal Parking Garage right around the corner from the hotel. We found it very convenient to park there (including overnight parking). It's open 24 hours, clean, has stairs and elevators to get to the street.
Reviewed on Oct 28, 2025


Park Central South Beach
South Beach
Price was $1,051, price is now $524 per person
$524
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (217 reviews)
I loved staying at this hotel. Super clean and modern but with a home feel. The staff are incredible. I will book it again
Reviewed on Oct 29, 2025

May-Dee Suites
Hollywood Hills
Price was $1,049, price is now $524 per person
$524
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,412 reviews)
If U are in the area just needing some where reasonable this is a kool place.
Reviewed on Oct 30, 2025
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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
$262 nightly
The price is $295 total per night from Nov 19 to Nov 20
$295 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (99 reviews)
View was beautiful. Parking lot clean. The staff could use more training on guest interaction. Drink prices way to high.
Reviewed on Oct 18, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $172 total per night from Nov 3 to Nov 4
$172 total
Nov 3 - Nov 4
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Beautiful place, nice room
Reviewed on Oct 24, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$169 nightly
The price is $190 total per night from Nov 2 to Nov 3
$190 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (827 reviews)
the pool was my favorite part, love that it was 24 hours and it was gorgeous!
Reviewed on Oct 21, 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) | 
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