Fleming Key Vacation Packages

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Top Fleming Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (81 reviews)
First of all. DO NOT rent a car unless you plan on sight seeing. EVERYTHING you need is within a few blocks walk from this property. This property is a historic art deco building with a small courtyard leading you into the space. There is a small patio for use as well. Our room #10 ever had some beach chairs to use. We were three blocks from stepping on the sand. We were within 100 feet of Esplnana Way that was filled with restaurants. Just use Uber. But, If you do drive, there are 2-3 municipal parking garages a few blocks away to park for a reasonable rate. We left our rental there for over 36 hours and the fee was $40. I would recommend this quant property for a short stay. Oh, shopping at Lincoln was a short walk away as well.

Reviewed on Jul. 30, 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 16 - Sep 21
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
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
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Needs new sheets They felt like they had small balls from being super used Place need new bed with prosper new linen I stayed at a TownePlace for three nights that had better mattress and linen

Reviewed on Aug. 1, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 16 - Oct 20
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul. 26, 2025

Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on Jul. 30, 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 $186 per night from Aug 18 to Aug 19
CA $186
CA $280 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (1,399 reviews)
"Wow I would definitely be back What an amazing time Love the views the nicely kept property All round 5 stars"

Reviewed on Jul. 30, 2025

Beachside Resort & Residences
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 $256 per night from Aug 25 to Aug 26
CA $256
CA $381 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,665 reviews)
"We had an awesome girls trip here! The staff were accommodating in putting our two rooms next to each other. The 3 pools/pool bars are great and have fun activities daily! It’s so close to everything either a quick walk or Uber got us everywhere we needed to go. We will definitely be back!"

Reviewed on Jul. 30, 2025

Southernmost Beach Resort and Guesthouses
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 $169 per night from Sep 1 to Sep 2
CA $169
CA $268 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,490 reviews)
"Good value for your money, convenient location and a friendly, welcoming staff. As a pet friendly resort, perhaps in the future have a couple of dog friendly entertainment areas on the resort so owners and their fur babies can spend time together."

Reviewed on Jul. 29, 2025

Blue Flamingo Resort Key West
See all 2,784 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 $611. 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.