Raccoon Key Vacation Packages 2025/2026 from $739

Raccoon Key flight + hotel vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$739

per person

Nov 15 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,138

per person

Nov 15 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$754

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$893

per person

Nov 15 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$885

per person

Nov 15 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Top Raccoon Key hotels deals

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

$235 nightly

$264 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Pool

Pet friendly

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$233 total

Oct 28 - Oct 29

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Pool

Pet friendly

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Free Cancellation

$237 nightly

$266 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pool

Spa

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$186 total

Oct 15 - Oct 16

Total with taxes and fees

This eco-certified hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.

Pool

Free WiFi

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$161 total

Oct 5 - Oct 6

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.

Pool

Pet friendly

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West, FL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$159 total

Oct 5 - Oct 6

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.

Pool

Free airport shuttle

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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.

Frequently asked questions

How much are vacation packages to Raccoon Key?

Starting at just $739, flight and hotel packages are an ideal way to make your travel budget stretch further. Watch out Raccoon Key — here you come!

Where can I get the best vacation package deals for Raccoon Key?

It's difficult to beat Travelocity when it comes to crafting your Raccoon Key package deal. There are as many as 400 air carriers and 1,000,000 worldwide properties to choose from. Book your trip now and get ready to tick another amazing destination off your list.

Why should I purchase my Raccoon Key vacation package via Travelocity?

Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.

Can I save on my Raccoon Key car rental if I book it with hotels and flights?

Combining your flight, hotel and car into a Raccoon Key vacation package is a great way to score an amazing deal. Plus, having your own wheels gives you the freedom to make your way to all those amazing sights you're itching to see. Located 110 mi from Raccoon Key, Zoo Miami is one attraction that should have a place on your itinerary. Fill up the tank and make a day trip of it.

What is the best time of year to go to Raccoon Key?

You'll be able to avoid the tourist crowds and save cold, hard cash in August, September and October, which are the quietest times for tourism. Peak season months of January, February and July are naturally busier (and more expensive), but there's likely to be more going on around Raccoon Key. Lock in a hotel in and get a lot more bang for your buck. Room rates tend to be higher in .

Which airport is best for Raccoon Key?

Heading to Raccoon Key will see you touching down at Key West Intl. Airport (EYW). It's roughly 2 mi southwest of the downtown area.

Where should I stay when visiting Raccoon Key?

Many travelers opt to check in to the Catamaran with kayak. It's a great base for your Raccoon Key escape.