Fleming Key Vacation Packages

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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
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,003 reviews)
The property was quaint and had a lot of character. Staff was nice enough and location was walking distance to most things.

Reviewed on Aug. 7, 2025

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
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
best hotel best location

Reviewed on Aug. 7, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
Beautiful location! Helpful and friendly staff! Restaurant food was amazing and we loved the ice cream!

Reviewed on Aug. 6, 2025

President Villa

President Villa

3.5 out of 5
South Beach
per person
Oct 25 - Oct 31
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Right on one of the main boulevards, convenient parking nearby, clean room and polite staff. Limited breakfast options, expensive resort fee for amenities offered, no housekeeping offered unless u requested and stayed over 3 days.

Reviewed on Jul. 7, 2025

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Fleming Key Hotel Deals

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 $184 per night from Aug 12 to Aug 13
CA $184
CA $277 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (1,426 reviews)
Sister Time
"Fantastic experience from check in-out. Lovely property and staff were polite and helpful. The hotels concierge, Susan-AMAZING. She made us feel at home. From the welcoming champagne toast to her knowledge of the island, its treasures and hotspots, she is a GEM! We will be back."

Reviewed on Aug. 5, 2025

Beachside Resort & Residences
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 $157 per night from Sep 7 to Sep 8
CA $157
CA $254 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (1,523 reviews)
"The staff and the manager are so nice I had a small issue with my room after the first night and the manager was so kind to move us to a new and gave us a 50.00 bar credit for the inconvenience he was very understanding about the issue and took care of it right away this property is family friendly ..."

Reviewed on Aug. 4, 2025

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is CA $243 per night from Aug 24 to Aug 25
CA $243
CA $366 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (2,658 reviews)
"Very nice e property! Quiet area, but very convenient to local bus stop to Duval Street and other attractions. We would definitely stay here again. Be sure to try Frenchie’s Cafe across the street. Great brunch!"

Reviewed on Aug. 5, 2025

Southernmost Beach Resort and Guesthouses
See all 2,786 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 $810. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.