Windley Key Adventure Vacations 2026

Top Adventure vacation packages in Windley Key

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

Hotel Riu Plaza Miami Beach

Mid Beach

$644

per person

Dec 11 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

Avi Lux Stay

East Fort Lauderdale

$751

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,531

per person

Dec 7 - Dec 11

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

$3,001

per person

Jan 17 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,682 reviews)

72 Park - Miami Beach by Nomada

North Beach

Save 100% on your flight

$843

per person

Jan 17 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (355 reviews)

They gave me the worst room / 2nd floor in front of elevators that I could hear l day and night long … as well as street where constructions go meaning trucks all mornings … Room seems clean and nice at first but you realise quickly it’s poor quality material mostly the bed sheets very itchy and scratching as well as noise coming from other rooms … Last I requested en extra hour stay in the room and instead of saying we re full sorry they asked me for some extra dollars … if my asking would have been 3 or 4 pm check out why not but 12 instead of 11 … Long story short : seems nice form the outside, way more average from the inside …

Reviewed on Oct 24, 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

$1,026

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (152 reviews)

No complains, Everything super nice and clean.

Reviewed on Oct 25, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,531

per person

Dec 7 - Dec 11

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

$3,001

per person

Jan 17 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,682 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.

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$1,024

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,992

per person

Dec 31 - Jan 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

1 Hotel South Beach

South Beach

$1,585

per person

Jan 7 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,682 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.

Avi Lux Stay

East Fort Lauderdale

$547

per person

Dec 6 - Dec 10

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$10,232

per person

Jan 13 - Jan 17

found 19 hours 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

$1,621

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

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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.