Monroe County Vacations & Trips 2026 from CA $1,136

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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.

A beachside restaurant with white tables and chairs, palm trees, and a view of the sea.

A beach with clear water, palm trees, and people relaxing on the sand.

A beach with palm trees and white lounge chairs under a clear blue sky.

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

Top Monroe County Vacation Deals

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

Private Oasis at Arya

Coconut Grove

Save 100% on your flight

CA $1,136

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.6/10 Excellent! (1,034 reviews)

Beautiful apt at the Arya. The unit is nicely designed and has nice furnishings, washer dryer and an amazing balcony with full frontal view of Biscayne bay and Dinner Key. Parking included. The building in general is a bit older, is a condo type hotel, and units are individually owned or ownership groups likeMiami vacation rentals, This unit seems to be managed by MVR. Outdoor pool is a bit run down but it has a great setting over the grove. Fitness center also a bit run down but gets the job done and is above the penthouse - roof level. Can’t beat the location or price for the Grove.

Reviewed on Sep 16, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $17,208

per person

Oct 30 - Nov 6

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Andaz Miami Beach Resort & Spa

Mid Beach

Save 100% on your flight

CA $1,657

per person

Nov 22 - Nov 27

found 23 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Miami (MIA)

9.2/10 Wonderful! (390 reviews)

great!

Reviewed on Sep 20, 2026

1 Hotel South Beach

South Beach

Save 100% on your flight

CA $2,725

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

I’ve stayed here before and this time just felt different. I was placed in an outdated room without a standalone shower. the room view was a roof. the hotel smelled like sewer water. I wasn’t happy with my stay. I wont be staying here again. It def does not give 5 star anymore.

Reviewed on Sep 20, 2026

Soleado Hotel

East Fort Lauderdale

Save 100% on your flight

CA $1,291

per person

Nov 21 - Nov 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

9/10 Wonderful! (710 reviews)

Monroe County Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

CA $183

CA $309 total

Sep 23 - Sep 24

includes taxes & fees

9.2/10 Wonderful! (1,440 reviews)

"The best"

Reviewed on Sep 20, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

CA $196

CA $299 total

Oct 21 - Oct 22

includes taxes & fees

9.2/10 Wonderful! (1,778 reviews)

"Nice pool, great breakfast with seating outside with nice views"

Reviewed on Sep 19, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

CA $224

CA $354 total

Sep 28 - Sep 29

includes taxes & fees

8.6/10 Excellent! (3,602 reviews)

"There is a lot of hidden fees. There’s a $65/day fee for some dumb reason. There’s a $58/day car fee if you have a car. The beach was unusable and smelled god awful. We were lucky to have breakfast included but everything was an extra charge."

Reviewed on Sep 20, 2026

See all 8,302 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 $1,136, 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.

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.

See properties