Raccoon Key Beach Vacations

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Flight and Beach hotel deals 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

CA $924

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

Pier House Resort & Spa

Key West Historic District

CA $1,430

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

The Perry Hotel & Marina Key West

CA $978

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,705

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $1,028

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

8.8/10 Excellent! (3,487 reviews)

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3 Night Beach holidays in Raccoon Key

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

The Marker Key West Harbor Resort

Key West Historic District

CA $1,109

per person

Sep 18 - Sep 21

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,020 reviews)

Great location . Hotel was very nice and I would stay there again . However The resort fee is pretty steep and doesn’t really get you anything….

Reviewed on Aug 9, 2026

Pier House Resort & Spa

Key West Historic District

CA $1,181

per person

Sep 18 - Sep 21

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9/10 Wonderful! (1,253 reviews)

The Perry Hotel & Marina Key West

CA $1,120

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

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4 Night Beach holidays in Raccoon Key

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

Hyatt Vacation Club at Windward Pointe, Key West

CA $917

per person

Sep 14 - Sep 18

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,219 reviews)

Beautiful resort! Well kept, great staff! Only downfall of the on resort restaurant….. service fees are STEEP!

Reviewed on Aug 9, 2026

The Key West Hotel

Key West Historic District

CA $5,259

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

Ibis Bay Beach Resort

Northside Resort

CA $1,206

per person

Sep 13 - Sep 17

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

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

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See all available trips from Columbus to Raccoon Key

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What are some benefits when booking beach vacations in Raccoon Key?

When you travel to the beach in Raccoon Key, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

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

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Raccoon Key trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Raccoon Key?

There are quite a few things you can do to get cheap beach vacations in Raccoon Key. Prices range from CA $917, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Raccoon Key. These package deals let you save by booking your accommodation and your flight together with savings of up to 33.

Why should I book family beach vacations?

When you're travelling with the family to Raccoon Key, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Raccoon Key?

It's easy to find a beachfront vacation accommodation in Raccoon Key using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Raccoon Key as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Raccoon Key is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Key West. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.