Fleming Key Vacation Packages

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Top Fleming 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 21 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

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $12,126, price is now CA $5,774 per person
CA $5,774
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $28,467, price is now CA $15,626 per person
CA $15,626
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $3,193, price is now CA $1,955 per person
CA $1,955
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1,162 reviews)
I like that the ocean was a 2 min walk, and that party side of Miami was a short drive away.

Reviewed on Jun 25, 2026

Pantera Rosa

Pantera Rosa

4 out of 5
South Beach
Price was CA $2,257, price is now CA $1,420 per person
CA $1,420
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (72 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

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Fleming 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 Jun 28 to Jun 29
CA $178
CA $280 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very good! (2,449 reviews)
"Great"

Reviewed on Jun 26, 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! (3,401 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 $185 per night from Jun 29 to Jun 30
CA $185
CA $249 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very good! (1,249 reviews)
"This property is write down and was traditionally over priced for the stay. The gives run down Dexter vibes and was less than fabulous in its remodeling. One sad elevator and just a general sad run down hotel that might have been nice several decades ago even with the location. Parking was 100% full ..."

Reviewed on Jun 26, 2026

Hilton Garden Inn Key West / The Keys Collection
See all 2,702 properties in Fleming 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 Fleming Key due to COVID-19?
Our handy Customer Service Portal has useful information about canceling or changing your flight due to COVID-19. Before booking your tickets, it's smart to look over the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to Fleming Key that have flexible change policies?
Search for your affordable flights to Fleming Key, then tick the "No change fee" box directly below the "Flexible change policies" filter. It really is that simple. We know that travel plans change and flexibility is essential, so book with confidence with Expedia.
What are some of the general tips for travelers to Fleming Key during the COVID-19 outbreak?
In the era of COVID-19, traveling today comes with more challenges than usual. Cast your eye over these helpful tips before hopping on your plane to Fleming Key:
  • Find out if any travel restrictions apply to your origin and destination before locking in your flight. Also check if there are any special conditions you'll need to follow on arrival, such as installing a contact tracing app.
  • When you go through airport checkpoints, do not remove your face mask. You will be required to lower it briefly for identification purposes. Anyone refusing to wear a mask may face civil penalties and may also be escorted from the building.
  • To minimize the risk of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your pass directly to a TSA employee.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. You'll have to remove it for X-ray screening.
  • Empty your personal items from your pockets, like your wallet and phone, and place them in your carry-on rather than the bins. This will minimize handling during screening.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA employee will need to open and touch your bag for inspection.

Which airlines fly to Fleming Key?
Let Delta get you there. This top carrier offers 191 services per month to Key West Intl. Airport (EYW), a Fleming Key gateway.
How can I find cheap tickets to Fleming Key?
Book in advance, fly in or out of nearby airports, avoid school vacation time — there are plenty of ways! Another one is to take advantage of Expedia's "flexible dates" feature. Find a Fleming Key flight, then check out the prices for nearby dates. In the last seven days, the best price for a flight to Fleming Key was .
How much is a flight to Fleming Key?
In the last seven days, round-trip tickets to Fleming Key sold for as little as and reached a maximum price of . For one-way fares departing from (), the cheapest seat during this same period was only .
What are the most popular airports to fly into in Fleming Key?
Fleming Key's main airport is Key West Intl. Airport (EYW). Get your next awesome adventure underway by reserving an airfare on one of the 1119 flights per month to this destination.
When is the cheapest time to fly to Fleming Key?
Try to jet off early on in the week to nab the best airfare to Fleming Key. Tuesday is commonly the most economical day to take off, followed by Monday. Saturday typically has the highest fares. This is because lots of people prefer to begin their break on a weekend.
How much is a plane ticket to Fleming Key?
In the last seven days, flights to Fleming Key cost between and . Prices depend on multiple things, particularly the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Fleming Key employ COVID-19 cleanliness policies?
In response to the ongoing pandemic, the majority of airlines have adopted additional steps and actions to help their passengers and crew fly with peace of mind. These carriers include:
  • 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.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

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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.