Windley Key Vacation Packages 2026 from $735

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The Latest Windley Key vacation packages

Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach

South Beach

$735

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,649

per person

Dec 31 - Jan 3

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

President Hotel Villa

South Beach

Save 100% on your flight

$860

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,000 reviews)

Best Hotel ever!!! I will come back!!

Reviewed on Oct 10, 2026

Mondrian South Beach

South Beach

Save 100% on your flight

$748

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (3,024 reviews)

The Local House

South Beach

Save 100% on your flight

$1,003

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,001 reviews)

The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient

Reviewed on Oct 5, 2026

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Stay 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.

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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.

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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

$294 nightly

$330 total

Oct 18 - Oct 19

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

Oct 11 - Oct 12

Total with taxes and fees

8.2/10 Very Good! (1,003 reviews)

"This was a lovely hotel in a good location. Rooms were clean the staff was lovely! The only thing I would say was the water pressure wasn’t great and not very hot either. Breakfast was good."

Reviewed on Oct 9, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$149 nightly

$168 total

Oct 26 - Oct 27

Total with taxes and fees

9/10 Wonderful! (295 reviews)

"Amazing gym, really cool pool with waterfall, beautiful view of the sunrise on a small beach. Overall was super nice."

Reviewed on Oct 4, 2026

See all 2,644 properties in Windley Key

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.