Fleming Key Vacation Packages

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

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Top Fleming Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $2,655, price is now CA $1,319 per person
CA $1,319
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I loved that it was an unique property & easily accessible to everything.

Reviewed on Nov 5, 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 $15,066, price is now CA $7,188 per person
CA $7,188
per person
Feb 1 - Feb 4
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Marlin Hotel

The Marlin Hotel

4 out of 5
South Beach
Price was CA $2,561, price is now CA $1,373 per person
CA $1,373
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
Nice hotel. Room was clean. Bed and pillows very comfortable. Bathroom was tight but shower was nice. There was some light that shown in from the back alley. We didn’t like the fact that there was a mandatory $32.00 fee per person for a beach chair and towel. The weather was rainy but you still had to pay for it. Nice location a block to the beach. Lots of restaurants nearby.

Reviewed on Nov 4, 2026

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Price was CA $3,879, price is now CA $2,135 per person
CA $2,135
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,779 reviews)

YotelPad Miami

YotelPad Miami

4 out of 5
Downtown Miami
Price was CA $2,719, price is now CA $1,520 per person
CA $1,520
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very good! (543 reviews)
Hotel is in a good location if you are looking for one near the cruise port

Reviewed on Nov 2, 2026

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Fleming Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $320 per night from Nov 30 to Dec 1
CA $320
CA $448 total
Nov 30 - Dec 1
includes taxes & fees
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Nov 30 to Dec 1
CA $201
CA $315 total
Nov 30 - Dec 1
includes taxes & fees
Havana Cabana at Key West
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 $175 per night from Nov 17 to Nov 18
CA $175
CA $275 total
Nov 17 - Nov 18
includes taxes & fees
Blue Flamingo Resort Key West
See all 2,692 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

How much does a Fleming Key vacation package cost?
From as low as CA $1,319. Yes, you read that correctly. Our Fleming Key vacation packages are the easiest way to make your budget last longer. Combine your favorite flights, hotels and rental car and explore this top destination.
How do I get a cheap travel package to Fleming Key?
Lock in flights that suit your schedule, add a hotel room to your booking and watch how much you save with a Fleming Key vacation package. It's as easy as that! From hotels and flights to rental cars and activities, Expedia makes traveling cheap and easy. And with over 550 airlines and 1,000,000 hotels globally to pick from, you'll never be short of choice.
Where should I stay in Fleming Key?
Vacationers come from all corners of the globe to experience Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens in Fleming Key. Book yourself a room close to these wonderful attractions and visit them at your leisure.
How far in advance should I book my Fleming Key vacation?
It's difficult to pick the best time for airfares, but we normally say the earlier, the better. Many international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, fear not. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Fleming Key travel package include?
It all boils down to what sort of getaway you're thinking about. Fleming Key vacation deals can include flights, hotels and car rentals. You can mix and match to create the bundle that suits your budget and style. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Fleming Key travel package?
Discover deals to suit your budget with an Expedia package. Hotels, flights, rental cars — we're a one-stop shop for all of them. You'll save precious cash just for combining your bookings. Whether you're embarking on a ski trip or sipping cocktails on a beach, your perfect vacation is just clicks away.
Can I choose my airline with a Fleming Key Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in control. We have access to more than 550 partner airlines around the world, so you have options galore when planning your Fleming Key getaway.
If I'm not able to travel, can I cancel my Fleming Key vacation package?
Whether it's your flight or hotel, you can cancel or alter it. Locked in your Fleming Key vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We'll help you every step of the way.

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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.