Fleming Key Vacation Packages

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Top Fleming Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 8 - Jul. 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,017 reviews)
Beautiful property right on the beach.

Reviewed on May 31, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug. 17 - Aug. 23
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
Our experience here was excellent. Housekeeping was exceptionally great! The customer service and attention to detail was outstanding.

Reviewed on May 31, 2024

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Aug. 17 - Aug. 23
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (72 reviews)
Very nice place to stay near the beach l, very beautiful view of bay from room balcony

Reviewed on May 27, 2024

Amazing Apartments at H Beach House

Amazing Apartments at H Beach House

3.5 out of 5
Hollywood Beach
Save 100% on your flight
per person
Aug. 17 - Aug. 23
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (10 reviews)
We are very disappointed because the last 2 days of our stay a scaffolding was hunging for our full, out side balcony, to do maintenance of which we were not informed in any way, a jackhammer was drilled into the foundation, which greatly disturbed our peace and quiet due to the enormous noise and our privacy. We have a video recording of that and we believe we should receive compensation for this. We were literally chased out of our apartment.

Reviewed on May 3, 2024

Fleming Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from Jun. 4 to Jun. 5
CA $229
CA $337 total
includes taxes & fees
Jun 4 - Jun 5
8.8/10 Excellent! (1,519 reviews)
"The hotel was great!!! The staff was great. The property is on stock island and set back away from busy streets yet close to everything. Downtown key west was 5 minutes away. We rented a scooter and drove everywhere on that."

Reviewed on May 31, 2024

Oceans Edge Key West Resort, Hotel & Marina
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 $313 per night from Jun. 4 to Jun. 5
CA $313
CA $439 total
includes taxes & fees
Jun 4 - Jun 5
8.4/10 Very Good! (1,770 reviews)
"Can’t thank the front desk and shuttle service enough for their hospitality and amount of care they put into their work. Everyone was so accommodating and made sure we were taken care of. We will be back next time we return to Key West."

Reviewed on May 29, 2024

Margaritaville Beach House Key West
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $335 per night from Jun. 19 to Jun. 20
CA $335
CA $463 total
includes taxes & fees
Jun 19 - Jun 20
8.2/10 Very Good! (1,890 reviews)
"Friendly staff and beautiful location"

Reviewed on May 29, 2024

Southernmost Beach Resort
See all 2,678 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Fleming Key vacation package cost?
From as low as CA $822. 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.

Discover the most popular places to visit in Fleming Key

Image for Duval Street

Duval Street

4.5/5(161 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Image for Mallory Square

Mallory Square

4.5/5(148 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Image for Smathers Beach

Smathers Beach

4/5(56 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.