Monroe County Vacations & Trips 2026 from CA $1,305

Your Monroe County Vacation

Choose a vacation package to Monroe County and make travel planning easy. With the logistics organized before you depart, you can focus on enjoying every moment in this wonderful destination. Begin your trip to Monroe County with some time exploring Key West visiting popular sights like Smathers Beach and Mallory Square. Key Largo is another city that draws travellers from far and wide. John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill are two of the top places to see in this destination. When it's time to stop daydreaming and start doing, Expedia will help turn your Monroe County vacation into reality.

Top vacation destinations in Monroe County

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

Top Monroe County Vacation Deals

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

Clinton Hotel South Beach

South Beach

CA $1,305

per person

Jul 29 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.4/10 Very good! (1,725 reviews)

very nice，but hard to find a parking

Reviewed on Jun 19, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $15,626

per person

Jul 27 - Aug 1

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very good! (1 review)

Ibis Bay Beach Resort

Northside Resort

CA $1,338

per person

Aug 10 - Aug 17

found 23 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Key West (EYW)

8/10 Very good! (2,313 reviews)

Breakfast needs improvement because it lacks variety.

Reviewed on Jun 24, 2026

Pantera Rosa

South Beach

CA $1,365

per person

Sep 3 - Sep 9

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Miami (MIA)

8.8/10 Excellent! (72 reviews)

The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

President Hotel Villa

South Beach

CA $1,343

per person

Jul 29 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.2/10 Very good! (1,001 reviews)

Clean rooms and very friendly and he’ll staffs

Reviewed on Jun 17, 2026

Monroe County Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

CA $178

CA $280 total

Jun 28 - Jun 29

includes taxes & fees

8.4/10 Very good! (2,450 reviews)

"Great"

Reviewed on Jun 26, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

CA $268

CA $406 total

Jul 7 - Jul 8

includes taxes & fees

8.8/10 Excellent! (3,401 reviews)

"Disappointing that the breakfasts were not included as per their website. Found upon arrival that you had to be staying in the "Guest House" to get the free breakfast. $65.00 per day resort fees seems exorbitant as did the $50.00 per night to park our golf cart. Had a ceiling fan malfunction that ..."

Reviewed on Jun 25, 2026

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

CA $185

CA $249 total

Jun 29 - Jun 30

includes taxes & fees

8/10 Very good! (1,249 reviews)

"This property is write down and was traditionally over priced for the stay. The gives run down Dexter vibes and was less than fabulous in its remodeling. One sad elevator and just a general sad run down hotel that might have been nice several decades ago even with the location. Parking was 100% full ..."

Reviewed on Jun 26, 2026

See all 8,321 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 vacation package cost?

Our Monroe County vacation packages, which start at just CA $1,305, 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 vacation?

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 vacation package?

With a vacation 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 vacation package?

Whether it's your flight or hotel, yes, you can amend or cancel it. Booked your Monroe County vacation 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.