
Windley Key Vacations from $337
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

B Ocean Resort Fort Lauderdale Beach
East Fort Lauderdale
Save 100% on your flight
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (3,019 reviews)
Pros: Staff was very friendly and professional, room was very clean, comfortable mattress and pillows, restaurant food was very good, especially the blackened Mahi. Great location with private beach.
Cons: clipper rooms in serious need of refresh- worn carpets, fitted sheets elastic worn out so do not stay put and are pilly, entry door to room is open air and did not seal- open at bottom half inch, light visible all around. Wooden doors, cabinets all scuffed up/ scratched/ worn. Chair missing from room. Lock on sliding door to balcony broken. $48.59 resort fee per day and the beach pool was closed for a private event, the bar was also closed for the event, ran out of beach towels at 11am, beach service was limited with no gluten free food options, charged $35 for beach umbrella. $55+tax parking (valet and self park same price). No robes.
Reviewed on Aug 6, 2025

Casablanca Miami Beach
North Beach
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
5.8/10 (307 reviews)
It was great for beach access. Nothing in our room worked. Coffee pot was broke. Stove was broke. We had to switch on and off the breakers to use it. Toilet would tflush half the time.
Reviewed on Jun 21, 2025

Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
Beautiful location! Helpful and friendly staff! Restaurant food was amazing and we loved the ice cream!
Reviewed on Aug 6, 2025


Cavalier Hotel South Beach
South Beach
Save 100% on your flight
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
The property was quaint and had a lot of character. Staff was nice enough and location was walking distance to most things.
Reviewed on Aug 7, 2025
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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
$237 nightly
The price is $266 total per night from Aug 19 to Aug 20
$266 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (56 reviews)
"Great resort, excellent staff and customer service, I'll definitely coming back"
Reviewed on Aug 7, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Aug 13 to Aug 14
$154 total
Aug 13 - Aug 14
Total includes taxes and fees
8/10 Very Good! (999 reviews)
""Breakfast included" I don't consider that a breakfast, more like snacks. Needs improvement or no breakfast option."
Reviewed on Aug 4, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$140 nightly
The price is $158 total per night from Sep 8 to Sep 9
$158 total
Sep 8 - Sep 9
Total includes taxes and fees
7.6/10 Good! (811 reviews)
The most relaxing night
"Amazing group of people works in this hotel ! Super friendly can’t wait to come back again"
Reviewed on Aug 1, 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.
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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.