Windley Key Vacation Packages 2026 from $376

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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

$376

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

President Hotel

South Beach

Save 100% on your flight

$575

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,738 reviews)

Everything cleansing us grounds all beyond service. Great

Reviewed on Sep 9, 2026

President Hotel Villa

South Beach

Save 100% on your flight

$575

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

Private Oasis at Arya

Coconut Grove

$1,039

per person

Nov 11 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,034 reviews)

Great location and excellent amenities made for a wonderful weekend stay. The hotel was comfortable, convenient, and had everything we needed for a relaxing getaway!

Reviewed on Sep 8, 2026

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$703

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

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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

$248 nightly

$279 total

Sep 17 - Sep 18

Total with taxes and fees

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$147 nightly

$166 total

Sep 21 - Sep 22

Total with taxes and fees

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

"Everything was great!"

Reviewed on Sep 8, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$149 nightly

$168 total

Sep 13 - Sep 14

Total with taxes and fees

9/10 Wonderful! (287 reviews)

"Amazing customer service"

Reviewed on Sep 6, 2026

See all 2,716 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.