Raccoon Key Vacation Packages

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Top Raccoon Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $2,391, price is now CA $1,678 per person
CA $1,678
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,066 reviews)
The property is beautiful! It was lovely sitting on the balcony overlooking the pool and ocean. The pool was nice and warm which was terrific. It was perfect to have two bedrooms and two bathrooms. There is a restaurant on site, though I preferred taking an Uber to many fabulous restaurants near Duval Street. My favorite ice cream spot was Wicked Licks!

Reviewed on May 11, 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 $3,619, price is now CA $2,458 per person
CA $2,458
per person
Jun 26 - Jul 3
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
9.4/10 Exceptional! (1,034 reviews)
The 2 bedroom suite was space clean and every comfortable for our group of 5. When we needed more towels they came very fast with them. Will stay here again.

Reviewed on May 10, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $3,835, price is now CA $2,621 per person
CA $2,621
per person
Jun 26 - Jul 3
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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

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 $2,966, price is now CA $2,090 per person
CA $2,090
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,261 reviews)
Luved the location, quality of rooms, friendly staff, swimming pools, buffet breakfast & lunch.

Reviewed on May 9, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Old Town Key West
Price was CA $8,718, price is now CA $6,276 per person
CA $6,276
per person
Jul 1 - Jul 8
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (3 reviews)
The house was amazing, much more than we expected. We loved the pool area and the landscaping, both were maintained beautifully. The whole place was clean as a whistle!

Reviewed on Oct 7, 2023

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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 $220 per night from May 25 to May 26
CA $220
CA $325 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (2,224 reviews)
The only thing missing was a balcony

Reviewed on May 11, 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
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jun 8 to Jun 9
CA $253
CA $371 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,814 reviews)
We had not been there before, would have liked to have been on a higher floor. The staff offered to move us the next day but it wasn't worth doing all that. The breakfast was good, needs more options but everything tasted great. The room was clean, a/c didn't always keep up for some reason, so it ...

Reviewed on May 11, 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 $299 per night from May 25 to May 26
CA $299
CA $436 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,301 reviews)
Ants in the bathroom. They came to spray the first day but they returned hours later because there were cracks all over the bathroom. The shower didn’t properly seal so the bathroom floor was soaked after our showers. It needs some serious upkeep. Also informed them it was our honeymoon and that ...

Reviewed on May 11, 2026

Southernmost Beach Resort and Guesthouses
See all 3,145 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.