Fleming Key Vacation Packages

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Top Fleming Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $1,716, price is now CA $989 per person
CA $989
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
Hotel is 2 separate buildings, one down the street which we were in but not notified about prior. This building appears to be under renovation without a pool or water view. All rooms are along busy, loud A1A. AC barely work and water pressure is minimal.

Reviewed on Mar 25, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $10,482, price is now CA $4,328 per person
CA $4,328
per person
May 5 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (321 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

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,026, price is now CA $1,612 per person
CA $1,612
per person
May 4 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
Everything was perfect . I would stay there again

Reviewed on Mar 16, 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 $359 per night from Apr 19 to Apr 20
CA $359
CA $482 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (1,999 reviews)
The staff were great and helped me with all my questions about Key West. They helped organize shuttles to a from Downtown and recommended some amazing restaurants!!

Reviewed on Mar 25, 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 $468 per night from Apr 20 to Apr 21
CA $468
CA $616 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
Aside from a couple front desk staff that were fairly snippy, almost like asking a question was a burden— everything else was great!

Reviewed on Mar 25, 2026

Margaritaville Beach House Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $385 per night from Apr 13 to Apr 14
CA $385
CA $566 total
Apr 13 - Apr 14
includes taxes & fees
8.6/10 Excellent! (2,087 reviews)
Shuttle times are extremely accurate. Beautfil place with friendly staff. Only wish checkout time was a bit later. Elevators were out our entire stay. We were on third floor. The staff did offer to help carry our luggage up.

Reviewed on Mar 22, 2026

Beachside Resort & Residences
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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.