Windley Key Vacation Packages 2026 from $424

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The Latest Windley Key vacation packages

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

Barcelona Studios Guesthouse

South Beach

$424

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,714

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop 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

Pelican Hotel

South Beach

Save 100% on your flight

$573

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (499 reviews)

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$461

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,011 reviews)

Brickell Arch Sea View Balcony Free Parking by Palermo Home Miami

Brickell

Save 100% on your flight

$806

per person

Nov 19 - Nov 26

found 21 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

10/10 Exceptional! (2 reviews)

Great

Reviewed on Jul 28, 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

$240 nightly

$270 total

Sep 7 - Sep 8

Total with taxes and fees

9/10 Wonderful! (256 reviews)

"Our air conditioning did not work and would only circulate air. We told them a few times and they sent people who just closed the curtains and turned the air temp lower (even though it didn’t work). Were also a lot of small ants in the room and got bit in the night. They just kept a lot of the same ..."

Reviewed on Aug 30, 2026

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$156 nightly

$175 total

Sep 17 - Sep 18

Total with taxes and fees

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$135 nightly

$152 total

Aug 31 - Sep 1

Total with taxes and fees

See all 2,711 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.