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.

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$526

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)

The hotel gives a modern look on the website and it does have two sections so it should be specific as to where you will be booking away. Your room is because it is certainly night and day.

Reviewed on Sep 17, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,844

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

Lyfe Resort & Residences

Hollywood Beach

Save 100% on your flight

$668

per person

Dec 3 - Dec 6

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.4/10 Good! (30 reviews)

Pelican Hotel

South Beach

Save 100% on your flight

$679

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

nanana

Reviewed on Sep 14, 2026

EAST Miami Residences

Brickell

Save 100% on your flight

$1,321

per person

Dec 3 - Dec 6

found 13 hours 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

$1,321

per person

Dec 3 - Dec 6

found 13 hours 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

$6,844

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

Save 100% on your flight

$1,827

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

Don't see what you're looking for?

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.

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$526

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)

The hotel gives a modern look on the website and it does have two sections so it should be specific as to where you will be booking away. Your room is because it is certainly night and day.

Reviewed on Sep 17, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,844

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

Lyfe Resort & Residences

Hollywood Beach

Save 100% on your flight

$668

per person

Dec 3 - Dec 6

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.4/10 Good! (30 reviews)

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.

Elita Hotel

East Fort Lauderdale

Save 100% on your flight

$652

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (204 reviews)

Very helpful from the beginning to the end of our stay

Reviewed on Sep 14, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$11,298

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) 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

Balfour Miami Beach, a Registry Collection Hotel

South Beach

Save 100% on your flight

$700

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

The hotel gives a modern look on the website and it does have two sections so it should be specific as to where you will be booking away. Your room is because it is certainly night and day.

Reviewed on Sep 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

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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.