Monroe County Vacation Packages

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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 sign for the Key West Museum of Art & History at the Custom House.
FlightsFlightsHotelsHotels

Key West

Key West

Top Monroe County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Club - Pool - Gym - Parking - Heart of Brickell

The Club - Pool - Gym - Parking - Heart of Brickell

4 out of 5
Brickell
Price was CA $3,742, price is now CA $1,862 per person
CA $1,862
per person
Jan 18 - Jan 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
No reviews

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $4,711, price is now CA $2,249 per person
CA $2,249
per person
Dec 29 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)

Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

5 out of 5
Downtown Miami
Price was CA $5,475, price is now CA $2,821 per person
CA $2,821
per person
Jan 30 - Feb 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (111 reviews)
Remote control on tv was bit confusing to use they were not synched despite following the instructions from the host, I was able to get 1 out of the three TVs working. However, there was much to do in the area and watching TV was not a priority. Parking was a bit complicated at first.

Reviewed on Nov 13, 2026

Glam Miami Nightlife - Resort Pool - Downtown

Glam Miami Nightlife - Resort Pool - Downtown

4 out of 5
Downtown Miami
Price was CA $6,528, price is now CA $3,376 per person
CA $3,376
per person
Dec 29 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
10/10 Exceptional! (1 review)
Loved this stay! The place was PERFECT. Could not ask for more!! Will definitely staying here again next time I’m in Miami.

Reviewed on Oct 20, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $30,017, price is now CA $15,853 per person
CA $15,853
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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

Monroe County Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $259 per night from Nov 18 to Nov 19
CA $259
CA $395 total
Nov 18 - Nov 19
includes taxes & fees
Cheeca Lodge & Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $327 per night from Nov 29 to Nov 30
CA $327
CA $458 total
Nov 29 - Nov 30
includes taxes & fees
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Nov 29 to Nov 30
CA $171
CA $283 total
Nov 29 - Nov 30
includes taxes & fees
Havana Cabana at Key West
See all 8,262 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.
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Frequently asked questions

How much does a Monroe County vacation package cost?
Our Monroe County vacation packages, which start at just CA $1,862, 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

What to do in Monroe County

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Monroe County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.