
Windley Key Vacation Packages
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Top Windley Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.




President Hotel Villa
South Beach
Price was CA $2,201, price is now CA $1,227 per person
CA $1,227
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
Room was clean. Staff was helpful. Location was perfect.
Reviewed on Feb 5, 2026

The Penguin Hotel
South Beach
Price was CA $2,184, price is now CA $1,220 per person
CA $1,220
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Nice staff and great location on South Beach. The Penguin is clean and very comfortable.
Reviewed on Feb 7, 2026
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
The price is CA $600 per night from Feb 11 to Feb 12
CA $600
CA $766 total
Feb 11 - Feb 12
includes taxes & fees
9/10 Wonderful! (143 reviews)
Spotless room, friendly staff, excellent food
Reviewed on Feb 6, 2026

Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Feb 11 to Feb 12
CA $288
CA $368 total
Feb 11 - Feb 12
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
The room was so clean. I loved the whole resort. The view was amazing. The grounds were very well maintained. I will always stay at Fisher inn when I visit Islamorada
Reviewed on Jan 30, 2026

Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
The price is CA $445 per night from Feb 16 to Feb 17
CA $445
CA $501 total
Feb 16 - Feb 17
includes taxes & fees
9/10 Wonderful! (181 reviews)
Staff was wonderful,grounds beautiful & private! Quiet ,cozy laid back feel !
Reviewed on Feb 6, 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.
Discover 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.
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- Adults Only Resorts & in Seabreeze Trailer Park
- Beach Hotel Hotels in Venetian Shores
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- Venetian Shores Hotels
- Hotels near Windley Key Fossil Reef Geological State Park
- Anhinga Trail
- Anne's Beach
- Baker's Cay Resort Beach
- Bluefin Rock Harbor Marina
- Coco Plum Beach
- Coral Castle Museum
- Crane Point Museum and Nature Center
- Curry Hammock State Park
- Cutler Ridge Mall
- Dagny Johnson Key Largo Hammock Botanical State Park
- Duck Key Vacations
- Ernest F. Coe Visitor Center
- Everglades National Park
- Fiesta Key
- Florida City Vacations
- History of Diving Museum
- Homestead Miami Speedway
- Homestead Vacations
- Hurricane Monument
- Visit Seabreeze Trailer Park
- Visit Venetian Shores
- Islamorada Vacations
- Visit Islamorada
- Key Largo Vacations
- Marathon Vacations
- Marinelab Undersea Laboratory
- Mayor Roscoe Warren Municipal Park
- North Key Largo Vacations
- Plantation Key Vacations
- Visit Plantation Key
- Prime Outlets Florida City
- Sombrero Beach
- Sunset Park Beach
- Windley Key Fossil Reef Geological State Park
- Avis Rental Cars in Plantation Key
- Car rental Islamorada
- Convertible Car Rentals in Islamorada
- Luxury Car Rentals in Islamorada
- Mex Rent A Car Rental Cars in Plantation Key
- Pickup Car Rentals in Islamorada
- Pickup Car Rentals in Plantation Key
- Sixt Rental Cars in Islamorada
- Thrifty Car Rental Rental Cars in Islamorada
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







