
Windley Key Vacations from $263
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.



Flow Miami Hotel
Downtown Miami
Price was $2,580, price is now $1,210 per person
$1,210
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (160 reviews)
The room was awesome. Nice space, everything you could need. Gym was fab as was pool. Location spot on. All round win.
Reviewed on Nov 1, 2025

The Local House
South Beach
Price was $1,962, price is now $941 per person
$941
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Our room was spacious and clean with an incredible view. The rooftop pool and sitting areas were beautiful, and the staff was incredibly friendly and courteous.
Reviewed on Nov 5, 2025

Hawks Cay Resort
Price was $1,369, price is now $658 per person
$658
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,011 reviews)
Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.
Reviewed on Nov 7, 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.
What to do in Windley Key

Explore Mangrove Creeks with an All Day SUP/single kayak Rental
$47
per adult

Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
$65
per adult

Ft. Lauderdale to Key West Day Trip Quality Day Tours
$225
per adult
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
$271 nightly
The price is $304 total per night from Nov 19 to Nov 20
$304 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (104 reviews)
Good value for an off-season break in the Keys. The staff was excellent, helpful, and friendly. Easy parking close to our room. Lots to do inside the resort for no extra cost: kayaking, ping pong, corn hole, water taxi, nice swimming pools and loungers in the sun. Live music every night at the tiki ...
Reviewed on Nov 5, 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 Dec 4 to Dec 5
$172 total
Dec 4 - Dec 5
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Small , nice. Comfortable place We like it
Reviewed on Nov 5, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$169 nightly
The price is $190 total per night from Nov 16 to Nov 17
$190 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (137 reviews)
Perfect place to relax and unwind in the keys
Reviewed on Nov 7, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















