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.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$949

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,398 reviews)

I would stay here and recommend people to stay here again. The grounds are tucked into the property with trees, hammock chairs. The breakfast is exceptional for a free daily breakfast bartenders are friendly. The pools are relaxing. Everything‘s well kept. There’s not a lot of noise or overly restrictive rules. It’s a refreshing place to be and only a few walkable blocks to Duval

Reviewed on Sep 9, 2026

Lighthouse Suites Collection

Old Town Key West

Save 100% on your flight

$1,878

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

No reviews

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,417

per person

Dec 5 - Dec 9

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

The Marker Key West Harbor Resort

Key West Historic District

$1,132

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Where do I start. Half the electricity in the room didn’t work. We shared the room for 4 days with a small lizard. We contacted the front desk on the first night and they did nothing. The bed and pillows were right out of a Motel 6. No air conditioning in the hallways. They had a musty mildew smell. For a place trying to be an upscale place with a price that goes with it they failed miserably. The one positive was the young man who helped with the luggage.

Reviewed on Sep 9, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$952

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (3,560 reviews)

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3 Night Adventure vacations in Raccoon Key

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

The Marker Key West Harbor Resort

Key West Historic District

$1,011

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Reviewed on Sep 9, 2026

Lighthouse Suites Collection

Old Town Key West

Save 100% on your flight

$1,878

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

No reviews

The Gardens Hotel

Old Town Key West

$1,151

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

Reviewed on Sep 8, 2026

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

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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 Beach House, Key West

$941

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! (1,226 reviews)

Second year staying here, it was great!

Reviewed on Sep 9, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,817

per person

Dec 5 - Dec 9

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

$1,213

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,255 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

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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.