Stock Island Adventure Vacations 2026

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Top Adventure vacation packages in Stock Island

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

Hilton Key West Resort & Marina

$271

per person

Nov 29 - Dec 1

found 20 hours ago

Roundtrip flight included

Orlando (MCO) to Key West (EYW)

9/10 Wonderful! (1,831 reviews)

The Perry Hotel & Marina Key West

Save 100% on your flight

$357

per person

Nov 29 - Dec 1

found 20 hours ago

Roundtrip flight included

Orlando (MCO) to Key West (EYW)

9.4/10 Exceptional! (1,323 reviews)

Good place to stay but watch out for the gratuity tax (it's a State of Florida thing). The property was well maintained, and we enjoyed the room. Overall, it was a good place to stay. Most of the staff were hospitable and management was amazing.

Reviewed on Sep 27, 2026

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3 Night Adventure vacations in Stock Island

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

Hilton Key West Resort & Marina

$648

per person

Oct 28 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Amarillo (AMA) to Key West (EYW)

9/10 Wonderful! (1,831 reviews)

The Perry Hotel & Marina Key West

$703

per person

Nov 29 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,323 reviews)

Reviewed on Sep 27, 2026

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See all available trips from Columbus to Stock Island

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4 Night Adventure vacations in Stock Island

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

The Perry Hotel & Marina Key West

$830

per person

Nov 29 - Dec 3

just found

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

9.4/10 Exceptional! (1,323 reviews)

Reviewed on Sep 27, 2026

Hilton Key West Resort & Marina

$950

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,831 reviews)

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See all available trips from Columbus to Stock Island

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How can I book the best Stock Island adventure trips?

Choose your own adventure in Stock Island, 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 Stock Island family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Stock Island. 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 Stock Island 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 Stock Island adventure vacation for couples?

Book a Stock Island 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 Stock Island?

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 Stock Island 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.

Why should I book a Stock Island adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

Top Adventure Stock Island Hotels

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

4 min walk from Stock Island Yacht Club & Marina

Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...

Key West Yacht Life

Key West Harbour Yacht Club Stock Island Key West FL

3 min walk from Stock Island Yacht Club & Marina

Book a stay at this beach houseboat in Key West. Enjoy free WiFi, free parking, and a private beach. Popular attractions Duval Street and Smathers Beach are ...

Sail Florida Adventures

617 Front Street Key West FL

4 min walk from Stock Island Yacht Club & Marina

Book a stay at this beach houseboat in Key West. Enjoy free WiFi, a private beach, and a marina. Popular attractions Duval Street and Smathers Beach are located ...

See all 3,062 properties in Stock Island

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.