Windley Key Vacation Packages 2026 from $393

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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

$393

per person

Oct 31 - Nov 7

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

$7,435

per person

Oct 30 - Nov 3

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$536

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

I had a great stay! Thank you!

Reviewed on Sep 18, 2026

Miami Vacation Rentals - Brickell

Brickell

$1,319

per person

Dec 2 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

8.8/10 Excellent! (567 reviews)

Is a very nice property. SPA and Gym are very good. Very clean rooms with everything you need to make an apartment work (cleaning products, toiletries). The only bad thing was that the pool is closed an it will probably be by the entire year, they compensated with free wine and activites.

Reviewed on Sep 14, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

$986

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,180 reviews)

The rooms don’t have blankets, there was a “blanket” in the closet, but it was not even remotely soft and felt like covering up with a rug. The toilet was broken the whole stay, we had to fix it ourselves multiple times. The pool closed before dinner time. The property was a great location, the beach was beautiful, and staff was friendly, but for the price of the stay it felt very mediocre.

Reviewed on Sep 17, 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

$264 nightly

$297 total

Sep 27 - Sep 28

Total with taxes and fees

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$139 nightly

$156 total

Sep 21 - Sep 22

Total with taxes and fees

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

"Clean and comfortable rooms. I love the location relative to things to do in the Keys. We used the bikes while there and have used kayak/paddleboards in past. The staff is absolutely amazing. I had messed up the dates of the reservation. Jamal worked really hard to get me a room at a rate i could ..."

Reviewed on Sep 18, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

$149 nightly

$168 total

Sep 21 - Sep 22

Total with taxes and fees

9/10 Wonderful! (293 reviews)

"Excellent stay! Love this place and will definitely be back!"

Reviewed on Sep 18, 2026

See all 2,707 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.