Monroe County Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
- Rest easyPlan, book, and manage your trip all in one place
Top destinations in Monroe County
Key West
Marathon
Key Largo
Islamorada
Tavernier
Big Pine Key
Long Key
Top Flight + Hotel Deals in Monroe County
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
€449
per person
14 Nov - 18 Nov
found 9 hours ago
Return flight included
Washington (WAS) to Miami (MIA)
8.6/10 Excellent! (1,008 reviews)
Very surprised how great this stay was for the price!
The front desk guy was friendly!
This boutique hotel was the cutest!
This stay included lounge chairs, towels,water,ice and they even had an extra beach umbrella for us to use.
Me and 10 other friends stayed for 3 nights and no complaints!
High recommend staying here, right across the street from south beach and food and drinks everywhere!
Reviewed on 4 Oct 2026
Fontainebleau Miami Beach
Mid Beach
€747
per person
14 Nov - 18 Nov
found 9 hours ago
Return flight included
Washington (WAS) to Miami (MIA)
8.4/10 Very good! (9,051 reviews)
The hotel and property were excellent. I highly recommend it if coming to south beach.
Reviewed on 4 Oct 2026
Top hotels in Monroe County
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
€254
8 Oct - 9 Oct
includes taxes & fees
9.2/10 Wonderful! (1,470 reviews)
"Take a large was more than we expected. It was beautiful. It was clean. The service was amazing. The hotel had the perfect keys vibe. The beach was exactly what we needed. Perfect for group of friends families overall great hotel great food. Great drinks great bar service the rooms for spacious clean ..."
Reviewed on 4 Oct 2026
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
€201
6 Oct - 7 Oct
includes taxes & fees
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€265
6 Oct - 7 Oct
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 Monroe County holiday package cost?
Our Monroe County holiday packages, which start at just €351, are an easy way to save big bucks. All you have to do is choose your preferred hotels, flights and rental car to create your perfect trip.
How do I get a cheap travel package to Monroe County?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Choose the combination that suits you and see your savings pile up. We know a travel package is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Monroe County adventure.
Where should I stay in Monroe County?
You can't go wrong in Key West. Famous attractions, such as Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens, will keep you on the go in this lively city.
What are the top hotels in Monroe County?
When it comes to properties in Key West, Margaritaville Beach House Key West and Southernmost Beach Resort are two popular options. If you're also spending time in Marathon, 24 North Hotel Key West and Faro Blanco Resort & Yacht Club are waiting to welcome you.
How far in advance should I book my Monroe County holiday?
It all depends on the air carrier, but it's usually possible to compare international fares on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally score a cheaper seat just weeks prior to their intended journey.
What does an Expedia Monroe County travel package include?
You can choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like tours and activities. Want to pick your fare class? That's easily done too. The choice is yours when it comes to putting together your ideal Monroe County trip.
What should I know before booking a Monroe County travel package?
Our prices are already low. However, you'll pick up an even better deal when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Monroe County Expedia holiday package?
With a holiday package, you're the boss. Whether you want to fly to Monroe County in coach or first class, simply select from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Monroe County holiday package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Booked your Monroe County holiday package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may incur a fee from your hotel, airline or car rental company. For further information, look up our Customer Service Portal. We're here to help you every step of the way.
Stay near popular Monroe County attractions
Duval Street
9.2/10 (20,928 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.
Florida Keys Beaches
8.4/10 (858 reviews)
Nothing says holiday like spending a care-free day in Florida Keys Beaches, a popular beach in Long Beach Estates.
Southernmost Point
8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
Mallory Square
9.2/10 (15,939 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.
Sombrero Beach
9.0/10 (2,464 reviews)
Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.
Smathers Beach
8.4/10 (8,320 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
Dry Tortugas National Park
8.8/10 (2,184 reviews)
Separated from the mainland and encased by golden beaches and colorful coral reefs, this is a national park of fascinating ocean scenery.
Ernest Hemingway Home and Museum
9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
