Top Adventure vacation packages in Key West

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

Blue Flamingo Resort Key West

New Town

$600

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

7.8/10 Good! (1,586 reviews)

The room was clean and newly updated and the staff were pleasant and helpful.

Reviewed on Oct 3, 2025

Oceans Edge Key West Resort, Hotel & Marina

$811

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Sarasota (SRQ) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Overall just a good placecto saty whike yiur there

Reviewed on Oct 3, 2025

La Concha Key West, Autograph Collection

Key West Historic District

$861

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

9/10 Wonderful! (208 reviews)

Everything thing within walking distance. Fabulous dining and shopping.

Reviewed on Oct 3, 2025

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,036

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Sarasota (SRQ) to Key West (EYW)

8.6/10 Excellent! (2,750 reviews)

Hardly any beach view from our room. 4 adult woman staying in one room. We had to constantly ask for extra towels. Wash clothes, hand towels etc..

Reviewed on Oct 3, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$985

per person

Dec 4 - Dec 7

found 9 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Great and fabulous staff

Reviewed on Oct 3, 2025

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See all available trips from Columbus to Key West

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3 Night Adventure vacations in Key West

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

Oceans Edge Key West Resort, Hotel & Marina

$572

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Overall just a good placecto saty whike yiur there

Reviewed on Oct 3, 2025

Southernmost Beach Resort and Guesthouses

Old Town Key West

$734

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

8.6/10 Excellent! (2,750 reviews)

Hardly any beach view from our room. 4 adult woman staying in one room. We had to constantly ask for extra towels. Wash clothes, hand towels etc..

Reviewed on Oct 3, 2025

Blue Flamingo Resort Key West

New Town

$600

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Columbus (CMH) to Key West (EYW)

7.8/10 Good! (1,586 reviews)

The room was clean and newly updated and the staff were pleasant and helpful.

Reviewed on Oct 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Key West

View all trips

4 Night Adventure vacations in Key West

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

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$570

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip flight included

Raleigh (RDU) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Overall just a good placecto saty whike yiur there

Reviewed on Oct 3, 2025

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$874

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (375 reviews)

We really enjoyed our stay at Ella’s Cottages. It is a short walk to Duvall Street with lots of dining options close by. The suites were tucked into a beautifully landscaped property. I truly felt transported to a tropical island sanctuary. There were beach/pool towels on the lounge chairs by the pool. The pool itself is small but very clean and refreshing after a hot day. There were also tables in the pool area to dine or gather. We upgraded our room to a larger room with a patio. The bathroom was nicely updated and very clean. Our bedroom area also was nicely updated and clean. The window AC unit worked hard to cool our room on the lowest setting. The ceiling fan helped. The staff was very friendly and helped us find good suggestions of places to eat. The continental breakfast was: essentially it’s a basket of croissants or bagels, bottled orange juice, yogurt cups, coffee, cheese packets, detox shots and two egg bites. I would highly recommend Ella’s Cottages and would stay here again.

Reviewed on Sep 30, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,113

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Great and fabulous staff

Reviewed on Oct 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Key West

View all trips

How can I book the best Key West adventure trips?

Choose your own adventure in Key West, 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 Key West family adventure vacation?

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

Book a Key West 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 Key West?

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 Key West 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 Key West 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 Key West Hotels

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

11 min walk from Duval Street

Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...

8.6/10 Excellent! (2,788 reviews)

"Great"

Reviewed on Sep 28, 2025

Hyatt Centric Key West Resort and Spa

601 Front St, Key West, FL

11 min walk from Duval Street

Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...

8.8/10 Excellent! (1,023 reviews)

"Location was great! Staff outstanding! Can’t wait to go back!"

Reviewed on Sep 25, 2025

Heron House Court - Adult Only

412 Frances St, Key West, FL

11 min walk from Duval Street

Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. ...

8.8/10 Excellent! (1,005 reviews)

"Everyone was so nice, from the staff to the guests. We had a great time !"

Reviewed on Sep 25, 2025

See all 2,736 properties in Key West

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.