
Windley Key Vacations from $515
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Avi Lux Stay
East Fort Lauderdale
$515
per person
Nov 30 - Dec 5
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$6,948
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016

Hotel Victor
South Beach
$698
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,001 reviews)
Our room was perfect as we had a small balcony and view of South Beach and the pool right below our room. The staff was personable and made us feel welcome. The hotel is located in a great location right on South beach so we did not need to rent a car. The food at the restaurant was delicious.
Reviewed on Oct 14, 2026

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
$959
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,741 reviews)
Pros: Mark kindly allowed us to check in early after traveling all morning. Logan, the bellman, was friendly & cheerful. John was the hardest-working man on the beach, constantly checking on us and keeping us hydrated, even when we weren’t ordering from the menu. Our housekeeper, Marie L., kept our suite spotless & provided fresh towels with a smile. All 3 deserve recognition for their outstanding service!
The beachfront location on N. Ocean BLVD is convenient, & the $2 public bus along A1A is a budget-friendly alternative to Uber & Lyft.
Cons: The thin walls allowed hallway noise into our suite, and we could hear washing machines as early as 7 a.m.
Our biggest disappointment—and the reason we WON’T return—is the lack of a microwave! A lavish minibar & cute aqua-blue refrigerator, but no microwave? Restaurants serve generous portions, & we wasted considerable food & $$ because we couldn’t reheat leftovers. For a resort charging high rates & hefty resort fees, this basic amenity should be standard!
We also discovered by chance from a Las Olas shop owner that the resort offers a complimentary shuttle to Las Olas Boulevard & other stops along N. Ocean Boulevard. Why wasn’t this mentioned at check-in? Better communication could have saved us transportation expenses.
Final Verdict: We appreciate the excellent staff, but noise, wasted food, poor communication, & high resort fees outweigh the positives. This was our 2nd stay, & 2 visits are enough. We won’t be returning!
Reviewed on Oct 14, 2026

President Hotel Villa
South Beach
$693
per person
Dec 31 - Jan 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Buen lugar excelente ubicación cerca de todo
El único detalle es que las instalaciones son un poco antiguas, adicional no nos hicieron limpieza un dia en la habitación
Reviewed on Oct 11, 2026
Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all tripsStay near popular Windley Key attractions
Windley Key Fossil Reef Geological State Park
8.8/10 (184 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.
Hog Heaven
After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area, or enjoy its fishing spots.
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
$304 nightly
$342 total
Nov 3 - Nov 4
Total with taxes and fees

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$208 nightly
$234 total
Nov 8 - Nov 9
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"It was EXACTLY what I was looking for. Thank you! I wish I had more time to enjoy the super adorable room."
Reviewed on Oct 12, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
$149 nightly
$168 total
Oct 26 - Oct 27
Total with taxes and fees
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.



















