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.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was CA $1,734, price is now CA $1,232 per person
CA $1,232
per person
Jun 15 - Jun 20
found 19 hours ago
Roundtrip flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (1,267 reviews)
The layout of the property allowed for privacy and relaxation while still having areas to gather. The breakfast was outstanding and the staff were lovely. And the pools……I can’t say enough, they were stunning.

Reviewed on May 15, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $2,909, price is now CA $1,996 per person
CA $1,996
per person
Jun 15 - Jun 20
found 19 hours ago
Roundtrip flight included
Montreal (YMQ) to Key West (EYW)
9.2/10 Wonderful! (552 reviews)
The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $3,586, price is now CA $2,472 per person
CA $2,472
per person
Jul 3 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The property staff wasn’t as attentive as I would have hoped at a resort like this. The rooms were spacious and clean.

Reviewed on May 12, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $2,667, price is now CA $1,904 per person
CA $1,904
per person
Jul 23 - Jul 27
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
Large, clean room. Excellent staff. In suite laundry. Screened in balcony. Lovely property with a lovely pool and beach. Would absolutely stay here again

Reviewed on May 16, 2026

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $3,022, price is now CA $2,246 per person
CA $2,246
per person
Jul 6 - Jul 13
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,001 reviews)
I have rarely been so positively surprised by a hotel. The outdoor areas (pool, gardens, bar) were more spacious than I expected, and impeccably maintained. It is so tranquil and peaceful, yet so close to the action. The Master Suite was super nice - large balcony, private sauna, and 2 bathrooms. Would definitely come back.

Reviewed on May 14, 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 $197 per night from Jun 1 to Jun 2
CA $197
CA $299 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (2,231 reviews)
Great place to take your kids. They have a lot of games on the outside by the pool, which they have two pools . 4ft and 5ft deep . When we got here, we got upgraded to a king size room for $30 a night.. There was a weird smell all week in our a lot of noise clanking around not sure what it was. only ...

Reviewed on May 16, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
The price is CA $293 per night from Jun 10 to Jun 11
CA $293
CA $416 total
Jun 10 - Jun 11
includes taxes & fees
8.8/10 Excellent! (1,794 reviews)
Pool tiny and they let allow daily passes allowing a million little kids on weekends. The beach across the street was a cesspool.

Reviewed on May 15, 2026

Margaritaville Beach House Key West
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 $280 per night from Jun 11 to Jun 12
CA $280
CA $416 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (3,320 reviews)
Clean comfortable exquisite location--pricey

Reviewed on May 15, 2026

Southernmost Beach Resort and Guesthouses
See all 3,138 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

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.