Fleming Key Vacation Packages

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Top Fleming Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
Aug 6 - Aug 12
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
10/10 Exceptional! (3 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on May 31, 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
Aug 6 - Aug 12
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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
Save 100% on your flight
per person
Aug 6 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,100 reviews)
Not great standard for the price we paid. Pool and lazy river look much bigger on pictures than really are. The most of the staff were friendly. We requested two rooms next to each other and when we arrived one of the rooms was dirty, so they offered us room on different floor which was very inconvenient for us. Overall wasn’t bad experience but you can get the same stay in better price.

Reviewed on Jun. 25, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug 6 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (1,184 reviews)
Simply the best hotel in Miami!

Reviewed on Jun. 24, 2025

Pier Sixty-Six

Pier Sixty-Six

5 out of 5
East Fort Lauderdale
per person
Aug 6 - Aug 12
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (67 reviews)
This is amazing property with a wonderful staff!!

Reviewed on Jun. 23, 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 Jun 29 to Jun 30
CA $184
CA $277 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,243 reviews)
"Beautiful relaxing quiet place ocean view stay! We loved it!"

Reviewed on Jun. 24, 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 refundableReserve now, pay when you stay
The price is CA $314 per night from Jul 14 to Jul 15
CA $314
CA $446 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (2,549 reviews)
"Good accommodation cleanness variety of activities good location we had a great time"

Reviewed on Jun. 24, 2025

Southernmost Beach Resort and Guesthouses
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 $337 per night from Jul 13 to Jul 14
CA $337
CA $467 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,734 reviews)
June Trip
"It was a very pleasant stay, nice staff, close and clean beach."

Reviewed on Jun. 23, 2025

Margaritaville Beach House Key West
See all 2,805 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 $982. 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.