Raccoon Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Raccoon Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was CA $2,380, price is now CA $1,338 per person
CA $1,338
per person
Aug 10 - Aug 17
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8/10 Very good! (2,313 reviews)
Breakfast needs improvement because it lacks variety.

Reviewed on Jun 24, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $4,643, price is now CA $3,426 per person
CA $3,426
per person
Aug 10 - Aug 17
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was CA $2,644, price is now CA $2,065 per person
CA $2,065
per person
Aug 10 - Aug 17
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9/10 Wonderful! (951 reviews)
Staff is friendly, attentive and helpful. Continental Breakfast is fresh and the perfect start for a day of adventure. We were there for a destination wedding at the Hemingway House that is right across the street. Location could not have been any better.

Reviewed on Jun 1, 2026

Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Price was CA $3,767, price is now CA $2,975 per person
CA $2,975
per person
Aug 10 - Aug 17
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
8.8/10 Excellent! (195 reviews)
Clean room, helpful staff, good suggestions about local restaurants and areas to visit that you may not find on regular trip forums or AI. Beach view was not pretty due to sea weed deposits and smell of dead seaweed, but that’s seasonal.

Reviewed on Jun 22, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $1,858, price is now CA $1,485 per person
CA $1,485
per person
Sep 5 - Sep 9
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
Nice hotel. 5 days/4 nights stay. Free parking, but no free breakfast The room came with a fridge and a coffee maker, no microwave. 2 Restaurants in the property, but food is very expensive. Staff at check in don’t even smile at you, when they do it feels forced. Concierges were very nice. The shuttle to Key West is a great feature. One of the two pools was closed. The one pool was packed full every day. Room was great. Tile on the floors, hubby found bed uncomfortable. Our room had one King bed and a coffee table. It felt unfinished. It needs a small sofa or something, so you don’t have to use the bed to sit to eat or work on your laptop. Every room has a very spacious balcony. The gym is very well equipped.

Reviewed on Jun 22, 2026

Ready to book your vacation to Raccoon Key?

 

Choose your dates

Raccoon Key Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 5 to Jul 6
CA $178
CA $280 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (2,447 reviews)
"Lots of outdoor activities for the family."

Reviewed on Jun 25, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Jul 6 to Jul 7
CA $272
CA $410 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (3,411 reviews)
"Disappointing that the breakfasts were not included as per their website. Found upon arrival that you had to be staying in the "Guest House" to get the free breakfast. $65.00 per day resort fees seems exorbitant as did the $50.00 per night to park our golf cart. Had a ceiling fan malfunction that ..."

Reviewed on Jun 25, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jun 29 to Jun 30
CA $186
CA $249 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (1,248 reviews)
"One thing we did not like was that several guests were smoking in and around the pool area. There were many families, including ours, with children using the pool, and the cigarette smoke made it unpleasant. We also noticed there were no “No Smoking” signs posted around the pool. We hope the hotel ..."

Reviewed on Jun 25, 2026

Hilton Garden Inn Key West / The Keys Collection
See all 3,098 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Raccoon Key

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $62
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $36
per child
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $76
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See all activities in Raccoon Key

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.

Explore a world of travel with Expedia

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