Raccoon Key Vacation Packages

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Top Raccoon Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Price was CA $2,258, price is now CA $1,533 per person
CA $1,533
per person
Mar 15 - Mar 20
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Perfect place to stay in Key West in my opinion! The staff was so wonderful and I mentioned to the bartender we were eloping the night before and their gad a bottle of wine waiting for us in our room when we got back!

Reviewed on Feb 8, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $3,914, price is now CA $2,580 per person
CA $2,580
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on Jan 28, 2026

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was CA $2,907, price is now CA $1,945 per person
CA $1,945
per person
Mar 15 - Mar 20
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Yes, clean, good service

Reviewed on Feb 6, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $2,479, price is now CA $1,697 per person
CA $1,697
per person
Mar 15 - Mar 20
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
From check in to check out, the Perry Hotel met our expectations for a laid back vibe. All staff were kind and wished to make our stay memorable. Clean rooms, two wonderful restaurants on site and an hourly shuttle that leaves the resort on Stock Island that drops into Key West.

Reviewed on Feb 7, 2026

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was CA $4,035, price is now CA $2,783 per person
CA $2,783
per person
Mar 15 - Mar 20
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9/10 Wonderful! (1,006 reviews)
Great location - close to everything. Resort and rooms could use some love.

Reviewed on Feb 7, 2026

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Raccoon Key Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $645 per night from Feb 10 to Feb 11
CA $645
CA $825 total
Feb 10 - Feb 11
includes taxes & fees
8.6/10 Excellent! (3,062 reviews)
The location was great. The room could have been cleaner. There were fruit flies in the bathroom.

Reviewed on Feb 6, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $392 per night from Feb 9 to Feb 10
CA $392
CA $478 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (2,066 reviews)
Everything was fantastic

Reviewed on Feb 1, 2026

Ibis Bay Beach Resort
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $437 per night from Feb 9 to Feb 10
CA $437
CA $576 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...

Reviewed on Feb 3, 2026

Oceans Edge Key West Resort, Hotel & Marina
See all 3,232 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.
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Frequently asked questions

Can I cancel my flight booking to Raccoon Key due to COVID-19?
Head to our Customer Service Portal for important details about canceling or changing your flight because of COVID-19. Also, read through the terms and conditions of your preferred carrier before booking your trip to Raccoon Key.
What's the best way to find cheap flights to Raccoon Key that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to give you the most flexible airfares around. Simply check the "No change fee" box directly beneath the "Flexible change policies" subheading to find your dream flight to Raccoon Key.
What are some of the general tips for travelers to Raccoon Key during the COVID-19 outbreak?
With new safety guidelines in effect, travel looks a lot different nowadays. Here are some useful things to know before you head off to Raccoon Key:
  • Before you lock in a flight, check if any travel bans or restrictions apply — in both your origin and destination. Get the latest updates by reviewing government travel advisories.
  • Requirements state you must wear a face mask throughout your travel experience, including at security checkpoints. Be prepared to lower your mask for ID verification when asked.
  • Do not hand your boarding pass directly to a TSA officer. Instead, you should place the pass on the reader and then hold it up for the agent to visually inspect it.
  • TSA now allows passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for scanning.
  • Remove items from your pockets, such as your wallet, coins and keys, and put them in your carry-on instead of the bins. This will minimize handling during the screening process.
  • Separate any food you have for screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Raccoon Key?
Book your fare with Delta and then begin planning your Raccoon Key travel itinerary. This popular carrier offers 191 flights a month to Key West Intl. Airport (EYW), a major gateway.
How can I find cheap tickets to Raccoon Key?
One of the best ways to snare cheap tickets to Raccoon Key is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. You'll see the cheapest prices for nearby days. The best price for a flight to Raccoon Key in the last seven days was . Booking well in advance will generally help you get an even bigger bargain.
How much is a flight to Raccoon Key?
You could have purchased a return flight to Raccoon Key from anywhere between and in the last seven days. For one-way journeys taking off from (), the lowest price during this period was just .
What are the most popular airports to fly into in Raccoon Key?
The number one gateway to Raccoon Key, roughly 1119 flights land at Key West Intl. Airport (EYW) every month. Scout around for an amazing deal, book your seat and get ready to experience this popular region.
When is the cheapest time to fly to Raccoon Key?
If you're not set on your travel dates to Raccoon Key, fly out early in the week. The most economical day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with many vacationers choosing to take off on the weekend.
How much is a plane ticket to Raccoon Key?
In the last seven days, seats cost between and . Have a look at our fantastic deals to Raccoon Key, pick your favorite and then start packing your things!
Which airlines with flights to Raccoon Key employ COVID-19 cleanliness policies?
Social distancing is just the start of new travel industry strategies to help combat COVID-19. From the moment you collect your tickets, these airlines will bring you to Raccoon Key with comfort and confidence:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.