Monroe County Holidays 2026

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Top destinations in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.

A sunset over a beach with a wooden pier and a small structure on it.

A calm river with boats, lush greenery, and a clear blue sky.

Top hotels in Monroe County

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

Rp2.659.203

Rp4.296.754 total

24 Sept - 25 Sept

includes taxes & fees

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

Rp2.682.346

Rp4.016.528 total

23 Sept - 24 Sept

includes taxes & fees

9.2/10 Wonderful! (1,783 reviews)

"Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel."

Reviewed on 22 Sept 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

Rp2.853.200

Rp4.515.000 total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (3,607 reviews)

"Todo estaba perfecto menos la playa estaba extremadamente sucia"

Reviewed on 22 Sept 2026

See all 8,248 properties in Monroe County

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 , 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

A street with a pharmacy, a theater, and a yellow building.

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.

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