Fleming Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Fleming Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $23,537
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop 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
President Hotel Villa
South Beach
CA $2,133
per person
Dec 29 - Jan 5
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very good! (1,000 reviews)
Buen lugar excelente ubicación cerca de todo
El único detalle es que las instalaciones son un poco antiguas, adicional no nos hicieron limpieza un dia en la habitación
Reviewed on Oct 11, 2026
Icon Brickell Luxe Stays by IliosRentals
Brickell
CA $3,005
per person
Dec 31 - Jan 5
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
7.8/10 Good! (7 reviews)
no communication after i emailed them and messaged them on Expedia app, lot of thing broken in the unit. It was okay stay.
Reviewed on Oct 8, 2026
Ready to book your vacation to Fleming Key?
Fleming Key Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
CA $297
CA $424 total
Oct 15 - Oct 16
includes taxes & fees
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $178
CA $280 total
Oct 15 - Oct 16
includes taxes & fees
8.6/10 Excellent! (2,724 reviews)
"Grounds were kept clean, room was filthy. Never cleaned while we were there, and they left new towels in a bag attached to room door handle outside."
Reviewed on Oct 14, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $212
CA $329 total
Oct 15 - Oct 16
includes taxes & fees
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.
Frequently asked questions
How much does a Fleming Key vacation package cost?
From as low as CA $902. 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.
Explore a world of travel with Expedia
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- Simonton Court Historic Inn & Cottages
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights to Key West
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Halifax (YHZ) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Calgary (YYC) to Key West (EYW)
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights from Edmonton (YEG) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Boca Chica Nude Beach
- Visit White Street Gallery District
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Shipwreck Museum
- Visit Downtown Key West
- Crane Point Museum and Nature Center
- Sunset Park Beach
- Southernmost Point
- Curry Hammock State Park
- Calusa Beach
- Duval Street
- Fort East Martello Museum and Gallery
- Veterans Memorial Park & Beach
- Smathers Beach
- Marathon Vacations
- Mel Fisher Maritime Museum
- Sombrero Beach
- Mallory Square
- Visit Fleming Key
- Visit Key West Historic District
- Florida Keys Eco - Discovery Center
- Fort Zachary Taylor Historic State Park
- Harry S. Truman Little White House
- Visit Key West
- Seven Mile Bridge
- South Beach
- Key West Vacations
- All inclusive Vacation Packages Key West
- Visit Historic Seaport
- Clarence S. Higgs Memorial Beach Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
