Windley Key Adventure Vacations 2026

Top Adventure vacation packages in Windley Key

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

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$616

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,007 reviews)

Everything def

Reviewed on Sep 20, 2026

Pelican Hotel

South Beach

$851

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

Front Desk Staff was GREAT! We ate outside one night and the FOOD was DEEEE-LISH-US!!!! The only two dislikes were the bed was extremely hard. Was not comfortable...and...being on Ocean Dr, the music played until about 1am(ish). All we heard was the Bass. So if you are an early "bedder", you may not want to stsy as any hotel on Ocean Drive. But overall, the Pelican was nice! (PS: the food was really good!!)

Reviewed on Sep 21, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,160

per person

Nov 26 - Nov 29

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

Mondrian South Beach

South Beach

Save 100% on your flight

$649

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (2,990 reviews)

After a relaxing massage, I decided to stay the night however, when I got to the front, the credit card machine kept giving an error when using my debit card. Nothing was wrong with my debit card. The front desk tried several times. This was very frustrating since I knew nothing was wrong with my card to take the resort fee.

Reviewed on Sep 21, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$1,182

per person

Dec 4 - Dec 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

CLEAN ROOM , WIFI NOT GOOD , NO TV SHOW . CLOSE TO THE BEACH

Reviewed on Sep 21, 2026

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5* Adventure vacations in Windley Key

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

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

$924

per person

Dec 10 - Dec 15

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (83 reviews)

Amazing

Reviewed on Sep 21, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,160

per person

Nov 26 - Nov 29

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

EAST Miami Residences

Brickell

$2,023

per person

Nov 26 - Dec 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

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See all available trips from Columbus to Windley Key

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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

$401

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

Reviewed on Sep 21, 2026

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$475

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,007 reviews)

Everything def

Reviewed on Sep 20, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,160

per person

Nov 26 - Nov 29

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

Don't see what you're looking for?

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.

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$616

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,007 reviews)

Everything def

Reviewed on Sep 20, 2026

President Hotel

South Beach

Save 100% on your flight

$799

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,995

per person

Oct 30 - Nov 3

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

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

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.