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

$733

per person

Mar 3 - Mar 5

found 21 hours ago

Roundtrip non-stop flight included

Orlando (ORL) to Key West (EYW)

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

Staff was excellent! We enjoyed the pool and especially the complimentary shuttle downtown.

Reviewed on Feb 1, 2026

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,325

per person

Mar 3 - Mar 6

found 23 hours ago

Roundtrip flight included

Charlotte (CLT) to Key West (EYW)

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

The hotel was very nice. Beautiful beach & pool. We had a little difficulty with check in as we arrived during a storm a the room we booked was still occupied by someone who extended their stay. Within 24 hours we were in the room we booked

Reviewed on Jan 31, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,431

per person

Mar 3 - Mar 6

found 23 hours ago

Roundtrip flight included

Charlotte (CLT) to Key West (EYW)

8.4/10 Very Good! (433 reviews)

Room was clean. Amenities were good

Reviewed on Jan 31, 2026

Oceans Edge Key West Resort, Hotel & Marina

$1,024

per person

Apr 3 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

It was a wonderful experience

Reviewed on Jan 31, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$875

per person

Mar 3 - Mar 5

found 21 hours ago

Roundtrip non-stop flight included

Orlando (ORL) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

Room was clean, hot water practically non existent and no in room communication with front desk, they rely on guests using their own cell phones to call the concierge’s who only answer when they are on duty! We experienced a propane leak in our room overnight and couldn’t contact anyone to after 8:00 am when they came on duty. The breakfast is served on a patio which has a large pigeon problem flying on to the tables to peck at food that was left on plates.

Reviewed on Feb 1, 2026

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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

Save 100% on your flight

$952

per person

Mar 3 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

It was a wonderful experience

Reviewed on Jan 31, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,528

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Room was very damp. One front desk rep was snippy when we had to change our room due to extended stay due to weather. Also was supposed to get free bkst but was not honored.

Reviewed on Jan 27, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,059

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

Room was clean, hot water practically non existent and no in room communication with front desk, they rely on guests using their own cell phones to call the concierge’s who only answer when they are on duty! We experienced a propane leak in our room overnight and couldn’t contact anyone to after 8:00 am when they came on duty. The breakfast is served on a patio which has a large pigeon problem flying on to the tables to peck at food that was left on plates.

Reviewed on Feb 1, 2026

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See all available trips from Columbus to Key West

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4 Night Adventure vacations in Key West

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

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$942

per person

Apr 5 - Apr 9

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.2/10 Very Good! (2,000 reviews)

Everything was fantastic

Reviewed on Feb 1, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,727

per person

Apr 3 - Apr 7

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

Room was very damp. One front desk rep was snippy when we had to change our room due to extended stay due to weather. Also was supposed to get free bkst but was not honored.

Reviewed on Jan 27, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,178

per person

Apr 3 - Apr 7

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

It was a wonderful experience

Reviewed on Jan 31, 2026

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See all available trips from Columbus to Key West

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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! (3,034 reviews)

Nice clean resort! Great fun time!

Reviewed on Jan 26, 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! (1,007 reviews)

Our room was clean, staff was very friendly and accommodating. The location was perfect…plan to return.

Reviewed on Jan 26, 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! (1,017 reviews)

A very pleasant place to stay. Close to everything, clean and great front desk staff. Breakfast was light and nice. My room was clean and quaint and comfortable. Highly recommend.

Reviewed on Jan 30, 2026

See all 2,774 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.