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.

The Perry Hotel & Marina Key West

$554

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

The music off the pool although the Saturday before we left the band couldn’t make it which was disappointing since it was so good every day they were there

Reviewed on Aug 9, 2026

Pier House Resort & Spa

Key West Historic District

$753

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$800

per person

Oct 10 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

La Concha Key West, Autograph Collection

Key West Historic District

$1,692

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (445 reviews)

Lighthouse Suites Collection

Old Town Key West

Save 100% on your flight

$2,469

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

No reviews

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3 Night Beach vacations in Raccoon Key

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

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$662

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$760

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

The Perry Hotel & Marina Key West

$1,052

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

The music off the pool although the Saturday before we left the band couldn’t make it which was disappointing since it was so good every day they were there

Reviewed on Aug 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

View all trips

4 Night Beach vacations in Raccoon Key

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

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$598

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.2/10 Very Good! (2,319 reviews)

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,294

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip 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

The Perry Hotel & Marina Key West

Save 100% on your flight

$638

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

The music off the pool although the Saturday before we left the band couldn’t make it which was disappointing since it was so good every day they were there

Reviewed on Aug 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Raccoon Key

View all trips

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 $554. 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

26 min drive from Florida Keys Beaches

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

26 min drive from Florida Keys Beaches

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.