Raccoon Key Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
$994
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Not as advertised. The rooms are small and dark with lots of unacceptable wear and tear. Our AC did not work upon arrival and required maintenance. There are no closets or storage but they had a wheel in clothing rack. Ants in our room. Lots of insane hidden fees…said it included a parking spot….but you pay for it. The fine print was crazy that they emailed and it was well over $500 in additional fees for our stay. The complimentary breakfast is also not as advertised and the breakfast items were stale and the exact same each day. It’s sold as luxury but it’s poor at best. An absolute catfish of a hotel on Expedia. It’s a Hilton partner property and they should be paying attention to this fake “luxury” property as well. Overall a very disappointing start! The staff was very nice but offered no solutions and nothing to even attempt to make our stay better.

Reviewed on Sep 8, 2026

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$1,385
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
I liked the place, the waterfront building allowed us to see a beautiful sunset. The amenities were okay, I just stayed a day and the restaurant was closed.

Reviewed on Sep 7, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
$2,740
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Absolutely beautiful place to spend our week! Everyone was kind and went out of their way to accommodate us!! Our room was beautiful and so comfortable. The only drawback to our cottage was the fact that there was black mold in the beautiful walkin shower and burnt out light bulbs. Disappointing for such a wonderful place! We made great friends and promise to be back next year!! One final note to ALL the hardworking staff...thank you all! Everyone worked hard to make things comfortable and amazing!! Our room was cleaned everyday by the sweetest team of gals. Breakfast was made and served every morning by the sweetest people! The Gardens Hotel has..hands down..the best team working there!!! Thank you to all!!

Reviewed on Sep 6, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$2,859
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
Save 100% on your flight
$1,396
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

3 Night Adventure vacations in Raccoon Key

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

Lighthouse Suites Collection

Old Town Key West
$1,148
per person
Nov 20 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
No reviews
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$1,385
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
I liked the place, the waterfront building allowed us to see a beautiful sunset. The amenities were okay, I just stayed a day and the restaurant was closed.

Reviewed on Sep 7, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
$1,455
per person
Nov 12 - Nov 15
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Absolutely beautiful place to spend our week! Everyone was kind and went out of their way to accommodate us!! Our room was beautiful and so comfortable. The only drawback to our cottage was the fact that there was black mold in the beautiful walkin shower and burnt out light bulbs. Disappointing for such a wonderful place! We made great friends and promise to be back next year!! One final note to ALL the hardworking staff...thank you all! Everyone worked hard to make things comfortable and amazing!! Our room was cleaned everyday by the sweetest team of gals. Breakfast was made and served every morning by the sweetest people! The Gardens Hotel has..hands down..the best team working there!!! Thank you to all!!

Reviewed on Sep 6, 2026

Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

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

Hyatt Vacation Club at Beach House, Key West

$1,090
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,226 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,088
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip 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 Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West
$1,213
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (419 reviews)
Room was great for long stays and families. A little outdated but the location was amazing! Easy walk to Mallory square and Duval street. Only complaint is a rooster waking us at 5 am but that’s Key West!

Reviewed on Sep 6, 2026

Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

Find awesome Raccoon Key adventure vacations

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.

Why should I book a Raccoon Key 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.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$42
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!

$45
per adult
92% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
See all activities in Raccoon Key

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.