Raccoon Key Adventure Vacations

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Top Adventure vacation packages in Raccoon Key

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

$975

per person

Nov 10 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,417

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

This was our first time at the Garden House and we LOVED it! Everything about the place was outstanding. So much, that we booked again to stay there in October, 2026. The staff, drinks, food, grounds....Everything is just wonderful.l

Reviewed on Sep 8, 2026

Lighthouse Suites Collection

Old Town Key West

Save 100% on your flight

$2,371

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

No reviews

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,349

per person

Nov 10 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

The Marker Key West Harbor Resort

Key West Historic District

$1,136

per person

Nov 10 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Great location! Close to everything! 56 dollar a day resort fee for what? A pool I haven’t used and ??? Sorry, this is insane! Besides this is an upscale Hotel with friendly staff. . At our room the a/c has blown straight onto the bed. Still suffering from this…

Reviewed on Sep 10, 2026

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3 Night Adventure vacations in Raccoon Key

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

Lighthouse Suites Collection

Old Town Key West

$858

per person

Oct 11 - Oct 14

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

No reviews

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,174

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Reviewed on Sep 8, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,349

per person

Nov 10 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

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4 Night Adventure vacations in Raccoon Key

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

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,171

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (419 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,436

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,173

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,255 reviews)

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How can I book the best Raccoon Key adventure trips?

Choose your own adventure in Raccoon 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 Raccoon Key family adventure vacation?

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

Book a Raccoon 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 Raccoon 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 Raccoon 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.