Windley Key Vacation Packages 2026 from $543

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Windley Key vacation packages

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

Park Royal Miami Beach managed by Accor

North Beach

$543

per person

Oct 3 - Oct 10

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (188 reviews)

we enjoyed our stay!

Reviewed on Aug 28, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,807

per person

Nov 17 - Nov 20

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

Park Central South Beach

South Beach

$1,202

per person

Nov 4 - Nov 11

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,850 reviews)

President Hotel

South Beach

Save 100% on your flight

$572

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,718 reviews)

Staff was helpful with everything we needed for our stay, well recommended place to stay

Reviewed on Aug 31, 2026

President Hotel Villa

South Beach

Save 100% on your flight

$565

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

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.

See properties

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.

See properties

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! (258 reviews)

"we loved it !!!"

Reviewed on Aug 31, 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

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

"The room itself was clean but the property needed updated"

Reviewed on Aug 31, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$133 nightly

$149 total

Oct 1 - Oct 2

Total with taxes and fees

9/10 Wonderful! (285 reviews)

"La propiedad en general estaba muy limpia, el personal bien atento, la piscina increíble, tiene una vista al mar espectacular y un desayuno estupendo, lo recomiendo"

Reviewed on Aug 31, 2026

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.