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.
Broadway Suites Downtown by RocketStay

Broadway Suites Downtown by RocketStay

3.5 out of 5
Coral Way
Price was CA $1,976, price is now CA $1,054 per person
CA $1,054
per person
Jan 23 - Jan 30
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.6/10 Excellent! (230 reviews)
Affordable hotel near downtown Miami. Convenient check-in and quick communication with the host!

Reviewed on Nov 4, 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 $31,504, price is now CA $14,782 per person
CA $14,782
per person
Jan 24 - Jan 29
found 21 hours ago
Roundtrip flight included
Toronto (YTO) 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

Miami Vacation Rentals - District 225

Miami Vacation Rentals - District 225

3.5 out of 5
Downtown Miami
Price was CA $3,595, price is now CA $1,938 per person
CA $1,938
per person
Jan 23 - Jan 30
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (6 reviews)
The apartment had not been cleaned thoroughly. The bed sheets were not clean and the floor was dirty. I would appreciate it if the cleaning could be done more carefully in the future.

Reviewed on Sep 7, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $2,916, price is now CA $1,589 per person
CA $1,589
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

Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

5 out of 5
Downtown Miami
Price was CA $2,176, price is now CA $1,240 per person
CA $1,240
per person
Jan 24 - Jan 29
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (111 reviews)

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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 $324 per night from Nov 18 to Nov 19
CA $324
CA $453 total
Nov 18 - Nov 19
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 $203 per night from Nov 29 to Nov 30
CA $203
CA $319 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (1,906 reviews)
"We had a great stay at the Havana Cabana. Love the pool! Clean room & very friendly staff."

Reviewed on Nov 9, 2026

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 $177 per night from Nov 15 to Nov 16
CA $177
CA $278 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (2,784 reviews)
"The ocean view was across a busy highway with other guests walking past the window. The tv volume would not go lower than 14. The staff was friendly. The plugs were very difficult to use. Cleaning staff tidied up but did not clean up. The lighting in the rooms is very dim. Overall a nice hotel. Just ..."

Reviewed on Nov 9, 2026

Blue Flamingo Resort Key West
See all 2,679 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 $1,054. 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.