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

$961

per person

Feb 21 - Feb 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Everything was as expected and staff were wonderful

Reviewed on Jan 22, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,147

per person

Mar 24 - Mar 27

found 22 hours ago

Roundtrip non-stop flight included

Manchester (MHT) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

The room was very clean and nicely located. The staff was very friendly and accomodating.

Reviewed on Jan 21, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,581

per person

Feb 21 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Clean room, and amenities

Reviewed on Jan 22, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$1,409

per person

Mar 24 - Mar 27

found 22 hours ago

Roundtrip non-stop flight included

Manchester (MHT) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Beautiful historic hotel, room was spacious, lots of amenities, friendly staff, terrific views, can walk to town.

Reviewed on Jan 20, 2026

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$1,221

per person

Mar 24 - Mar 27

found 22 hours ago

Roundtrip non-stop flight included

Manchester (MHT) to Key West (EYW)

8.4/10 Very Good! (1,001 reviews)

The room was very clean, well appointed and very comfortable

Reviewed on Jan 19, 2026

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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.

Blue Flamingo Resort Key West

New Town

Save 100% on your flight

$1,033

per person

Feb 21 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Key West (EYW)

8/10 Very Good! (1,693 reviews)

Everything was as expected and staff were wonderful

Reviewed on Jan 22, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,264

per person

Feb 21 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

The room was very clean and nicely located. The staff was very friendly and accomodating.

Reviewed on Jan 21, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,581

per person

Feb 21 - Feb 24

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Clean room, and amenities

Reviewed on Jan 22, 2026

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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,280

per person

Mar 24 - Mar 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (831 reviews)

The location was awesome and the staff was kind and attentive but the room was not great. First, the shower was tiny and took a long time to produce hot water. Sometimes, the water never got hot and was luke warm or even luke cold. The shower floor was spongy and the shower head was basic. The hotel provided shampoo and conditioner but we noticed that the shampoo, body wash, and hand soap were all the same product. The bed was comfortable but the room had plantation shutters that let in a lot of light at night. We could not make the room fully dark. The roosters started crowing around 3:30am and sounded like they were right outside the room, making it difficult to sleep. If I visit Key West again, I’d choose to stay someplace else because I need to sleep and shower comfortably.

Reviewed on Jan 21, 2026

Oceans Edge Key West Resort, Hotel & Marina

$1,584

per person

Feb 21 - Feb 25

found 15 hours ago

Roundtrip non-stop flight included

Asheville (AVL) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

The room was very clean and nicely located. The staff was very friendly and accomodating.

Reviewed on Jan 21, 2026

Pier House Resort & Spa

Key West Historic District

$1,910

per person

Feb 21 - Feb 25

found 15 hours ago

Roundtrip non-stop flight included

Asheville (AVL) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Clean room, and amenities

Reviewed on Jan 22, 2026

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

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.6/10 Excellent! (3,008 reviews)

NA but view from restaurant on beach great

Reviewed on Jan 20, 2026

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 helpful staff in our reviews. ...

8.8/10 Excellent! (1,002 reviews)

Clean room, nice staff

Reviewed on Jan 18, 2026

Heron House Court - Adult Only

412 Frances St Key West FL

11 min walk from Duval Street

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

9/10 Wonderful! (1,003 reviews)

The staff was wonderful! The room was clean and functional. The location was excellent. This building is a couple blocks from the Dry Tortuga ferry terminal which worked well for us. That said, this is an older building with character. If you're looking for a spotless new consruction, look elsewhere. ...

Reviewed on Jan 18, 2026

See all 2,768 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.