Windley Key Vacation Packages 2026 from $710

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The Latest Windley Key vacation packages

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

Avi Lux Stay

East Fort Lauderdale

$710

per person

Nov 19 - Nov 23

found 2 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,510

per person

Nov 29 - Dec 4

found 22 hours 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

Cavalier Hotel South Beach

South Beach

$1,308

per person

Dec 29 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

Great location. Reasonable price and very friendly staff!

Reviewed on Oct 16, 2026

The Penguin Hotel

South Beach

Save 100% on your flight

$894

per person

Dec 2 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,996 reviews)

The hotel was clean and the staff helpful.

Reviewed on Oct 20, 2026

President Hotel

South Beach

Save 100% on your flight

$798

per person

Dec 2 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,812 reviews)

The bathroom in my room was very very small. The closet area was larger. Very uncomfortable to use bathroom.

Reviewed on Oct 20, 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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What to do in Windley Key

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

$69

per adult

100% of travellers recommend

Snorkel and Sandbar Combo Adventure in Islamorada

$111

per adult

Kayak through Mangrove Forests in the Florida Keys

$65

per adult

100% of travellers recommend

See all activities in Windley Key

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

$304 nightly

$342 total

Nov 2 - Nov 3

Total with taxes and fees

9/10 Wonderful! (296 reviews)

"We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return ."

Reviewed on Oct 19, 2026

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$178 nightly

$200 total

Oct 21 - Oct 22

Total with taxes and fees

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$149 nightly

$168 total

Oct 26 - Oct 27

Total with taxes and fees

See all 2,661 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.