Windley Key Adventure Vacations 2026

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Top Adventure vacation packages in Windley Key

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

Bay Breeze Premium Apartments By Eskape Collection

Save 100% on your flight

$629

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (238 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

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

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$959

per person

Nov 6 - Nov 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

When we first arrived at the hotel the staff Clariza or Clarisa was very rude and disrespectful. She told us about a reservation fee and I asked for more clarification regarding that fee. She got smart and snatched the card and said it’s $165 along with a $250 deposit.

Reviewed on Sep 15, 2026

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

EAST Miami Residences

Brickell

Save 100% on your flight

$1,292

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

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5* Adventure vacations in Windley Key

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

EAST Miami Residences

Brickell

Save 100% on your flight

$1,292

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

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

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

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3 Night Adventure vacations in Windley Key

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

Pelican Hotel

South Beach

Save 100% on your flight

$509

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

nanana

Reviewed on Sep 14, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,839

per person

Nov 19 - Nov 22

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

1 Hotel South Beach

South Beach

$3,500

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

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See all available trips from Columbus to Windley Key

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4 Night Adventure vacations in Windley Key

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$310

per person

Oct 20 - Oct 24

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

$11,386

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

New York (NYC) 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

President Hotel Villa

South Beach

Save 100% on your flight

$902

per person

Dec 2 - Dec 6

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

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How can I book the best Windley Key adventure trips?

Choose your own adventure in Windley Key, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Windley Key family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Windley Key. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Windley Key adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Windley Key adventure vacation for couples?

Book a Windley Key couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Windley Key?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Windley Key with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.