Windley Key Vacation Packages 2026 from $526

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The Latest Windley Key vacation packages

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

Solé Miami, A Noble House Resort

Ocean Four

Save 100% on your flight

$526

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (2,141 reviews)

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$638

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,008 reviews)

Bathroom unsafe for older people but clock.

Reviewed on Aug 24, 2026

Lyfe Resort & Residences

Hollywood Beach

Save 100% on your flight

$897

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7/10 Good! (1,792 reviews)

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

Save 100% on your flight

$1,017

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (1,681 reviews)

Private Oasis at Arya

Coconut Grove

Save 100% on your flight

$721

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,027 reviews)

Clean room, great location, friendly staff

Reviewed on Aug 22, 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

$272 nightly

$306 total

Sep 1 - Sep 2

Total with taxes and fees

9/10 Wonderful! (255 reviews)

"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."

Reviewed on Aug 23, 2026

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$147 nightly

$166 total

Sep 20 - Sep 21

Total with taxes and fees

8.2/10 Very Good! (1,015 reviews)

"Was Great! Everyone was super nice and helpful!"

Reviewed on Aug 23, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$140 nightly

$158 total

Aug 26 - Aug 27

Total with taxes and fees

See all 2,710 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.