Name: Key West Home on Deep Water Canal with Pool on Key Haven Road, Fisherman's Dream
Rating: 10

Top Beach vacation packages in Raccoon Key

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

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,153

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,151 reviews)

There were some issues with our room in the beginning. Mainly since it was Christmas time and regular staff was out on our checkin day. However, they accommodated all our requests the next day and made up for it.

Reviewed on Dec 30, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,267

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

Reception was courteous but housekeeping was terrible. Waitstaff was overwhelmed.

Reviewed on Jan 2, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,858

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

We absolutely loved the hotel! The house was classic Key west, so spotless, the staff was fantastic, the tortises and birds were definately entertaining, the pool was heavenly and being greeted with a glass of Proscuitta definately started the vacation off perfectly. We will definately be back!!

Reviewed on Dec 27, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,572

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,044 reviews)

We lived our stay at this beautiful resort. We definitely plan to return.

Reviewed on Jan 6, 2026

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$2,096

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,006 reviews)

4th time staying, great staff, location

Reviewed on Jan 7, 2026

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3 Night Beach vacations in Raccoon Key

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,085

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

Staff and amenities

Reviewed on Jan 8, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$2,363

per person

Feb 18 - Feb 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

Reception was courteous but housekeeping was terrible. Waitstaff was overwhelmed.

Reviewed on Jan 2, 2026

The Perry Hotel & Marina Key West

Save 100% on your flight

$1,195

per person

Feb 7 - Feb 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,151 reviews)

There were some issues with our room in the beginning. Mainly since it was Christmas time and regular staff was out on our checkin day. However, they accommodated all our requests the next day and made up for it.

Reviewed on Dec 30, 2025

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.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,186

per person

Mar 11 - Mar 15

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Clean, roomy excellent staff

Reviewed on Jan 7, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,175

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on Dec 12, 2025

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$2,200

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

Reception was courteous but housekeeping was terrible. Waitstaff was overwhelmed.

Reviewed on Jan 2, 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 $1,085. 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.

Lifetime memories/Private pool/WiFi/Dog OK/Self check-in-out/High Cleanliness!

Key West FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Duval Street and Smathers Beach are located ...

9.8/10 Exceptional! (15 reviews)

Disappointment

We loved our stay we love the owners. I did try to book the same dates for next year and had a lot of trouble. I called VRBO at least three times to help me. Got the ok and pricing from the owner and I could never get it to work. Then the unimaginable happened. Someone else booked it. All you guys ...

Reviewed on Mar 18, 2025

Key West Home on Deep Water Canal with Pool on Key Haven Road, Fisherman's Dream

Key West FL

11 min drive from Duval Street

Stay at this vacation home in Key West. Enjoy private pools, laundry facilities, and patios. Popular attractions Duval Street and Smathers Beach are located ...

10/10 Exceptional! (4 reviews)

Wonderful stay

Stayed for the month of March and it was wonderful. The house was as listed and the owner was great to deal with. We totally enjoyed the pool, the kayaks, and the flat top grill for cooking outside. On the first day of spring, we saw a mama and baby manatee in the canal. Another day, we saw a nurse ...

Reviewed on Apr 4, 2025

See all 3,249 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.