Raccoon Key Mountain Vacations and Getaways

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Top Mountain vacation packages in Raccoon Key

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

The Perry Hotel & Marina Key West

$1,154

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Should be free

Reviewed on Aug 16, 2026

Southernmost House - Adult Exclusive

Old Town Key West

$2,089

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$2,059

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

Very private and personal. Breakfast and Bar was very nice and relaxing.

Reviewed on Aug 16, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$2,103

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Great location , able to walk to restaurants on Duval Street . Nice pools , good services

Reviewed on Aug 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

$2,561

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,002 reviews)

Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees.

Reviewed on Aug 14, 2026

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5* Mountain vacations in Raccoon Key

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

The Porch on Frances Inn

Old Town Key West

$1,782

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (137 reviews)

Great value

Reviewed on Aug 13, 2026

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3 Night Mountain vacations 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

$858

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

Very private and personal. Breakfast and Bar was very nice and relaxing.

Reviewed on Aug 16, 2026

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,930

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Reviewed on Aug 16, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,672

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,002 reviews)

Beautiful property, relaxing and enjoyable atmosphere, exceptional customer service!

Reviewed on Aug 14, 2026

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4 Night Mountain vacations 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

Save 100% on your flight

$841

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

Very private and personal. Breakfast and Bar was very nice and relaxing.

Reviewed on Aug 16, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,437

per person

Oct 19 - Oct 23

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

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$851

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (946 reviews)

This is a must stay property! It is walking distance to everything. Your very cold room with the softest mattress ever is always 7 minutes away or less.

Reviewed on Aug 13, 2026

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How to plan for a mountain vacation in Raccoon Key?

The first step to planning your mountain vacation to Raccoon Key is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Raccoon Key, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Raccoon Key, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Raccoon Key mountain vacation.

What amenities should I look for when booking a mountain resort in Raccoon Key?

When booking accommodation for your mountain vacation to Raccoon Key, check to see if where you're staying has heating. Raccoon Key's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Raccoon Key vacation package.

Why should I choose a package for my mountain vacation in Raccoon Key?

Choosing a package for your Raccoon Key vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a Raccoon Key package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Raccoon Key from $841. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Raccoon Key vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Raccoon Key all-inclusive vacation packages as these include all meals.

How can I book my Raccoon Key on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Raccoon Key mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Raccoon Key package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your Raccoon Key mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Raccoon Key vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to Raccoon Key are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Raccoon Key vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Raccoon Key vacation packages.

What types of mountain accommodations are available in Raccoon Key?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Raccoon Key. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.