Raccoon Key Beach Vacations

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Top Beach vacation packages in Raccoon Key

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

Blue Flamingo Resort Key West

New Town

$788

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (2,583 reviews)

The only complaint I have about this property is the fact after 11pm there are signs in the parking lot saying to go through the lobby. When you go through the property they tell you to walk outside at 1am outside of the parking lot to go your room. We absolutely love this property and felt this to be an inconvenience

Reviewed on Aug 11, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,375

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

Room was the perfect temperature. Chart room was a fun place to grab a late night drink. Location is perfect.

Reviewed on Aug 11, 2026

The Perry Hotel & Marina Key West

Save 100% on your flight

$884

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Parrot Key Hotel & Villas

Northside Resort

Save 100% on your flight

$972

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,433 reviews)

Do not even think about it, get it!

Reviewed on Aug 11, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,262

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

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3 Night Beach vacations in Raccoon Key

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

The Perry Hotel & Marina Key West

$715

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

$1,022

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$906

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

Room was the perfect temperature. Chart room was a fun place to grab a late night drink. Location is perfect.

Reviewed on Aug 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

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4 Night Beach vacations in Raccoon Key

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

Kona Kai Oasis

Old Town Key West

Save 100% on your flight

$993

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.2/10 Very Good! (642 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,080

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$1,285

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

Room was the perfect temperature. Chart room was a fun place to grab a late night drink. Location is perfect.

Reviewed on Aug 11, 2026

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See all available trips from Columbus to Raccoon Key

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How do I book the best Raccoon Key beach vacation packages?

Life’s a beach when you dive into our brilliant Raccoon Key beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Raccoon Key?

A rental steps from the shore creates an amazingly affordable Raccoon Key beach vacation. Seaside sojourns during low season start from $715. Prices and availability are subject to change. Additional terms may apply.

When should I book a Raccoon Key beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Raccoon Key?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Raccoon Key beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Raccoon Key vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Raccoon Key beach vacation deals?

Sort your search results by deals to delight in amazing Raccoon Key beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Raccoon Key beach trip with free cancellation and/or flexible dates?

Just like the Raccoon Key tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Raccoon Key beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Raccoon Key. (OK, maybe not that last part.)

Top Beach Raccoon Key Hotels

Floralee House in Key West

Key West FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.

Private & Haven-ly - Pool Home on Boating Canal

Key Haven FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Duval Street and ...

See all 3,103 properties in Raccoon Key

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.