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

FlightsFlightsHotelsHotels

Key West

Key West

Top Monroe County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was CA $2,118, price is now CA $991 per person
CA $991
per person
Jun 27 - Jun 30
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
2/10 (2 reviews)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $2,847, price is now CA $1,053 per person
CA $1,053
per person
Jun 30 - Jul 5
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
6/10 (2 reviews)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was CA $3,398, price is now CA $1,329 per person
CA $1,329
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
No reviews
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Price was CA $2,188, price is now CA $1,010 per person
CA $1,010
per person
Jun 20 - Jun 24
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
No reviews
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $5,268, price is now CA $2,528 per person
CA $2,528
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (323 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Monroe County Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jun 3 to Jun 4
CA $208
CA $311 total
Jun 3 - Jun 4
includes taxes & fees
8.4/10 Very Good! (2,227 reviews)
The staff was amazing & so sweet. the rooms are adorable & clean! both hotels have pools and bars and food plus cabanas. will be coming back again!

Reviewed on May 12, 2026

Blue Flamingo Resort Key West
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is CA $354 per night from Jun 1 to Jun 2
CA $354
CA $453 total
Jun 1 - Jun 2
includes taxes & fees
9.4/10 Exceptional! (1,439 reviews)
Great room, food, staff! Whatever the highest rating is, that's what the Reefhouse deserves!

Reviewed on May 12, 2026

Reefhouse Resort & Marina
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Jun 8 to Jun 9
CA $248
CA $365 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,816 reviews)
Staff was okay. The best wait staff was Hemanth. 10 stars! Above and beyond in service! Said margarita would be waiting for us when we arrived and we had to ask for it. No one really went the extra mile except Hemanth!

Reviewed on May 11, 2026

Margaritaville Beach House Key West
See all 8,361 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Monroe County vacation package cost?
Our Monroe County vacation packages, which start at just CA $991, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.