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
Top Monroe County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
South Beach
CA $856
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (506 reviews)
Resort Fee is something that we did not notice when we booked online through Expedia. We paid $45+tax extra per night.
Also, there is Service fee $3 per person for Breakfast that is included.
Reviewed on Sep 22, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $12,917
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip 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
EAST Miami
Brickell
CA $1,895
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (4,095 reviews)
EAST Miami is one of my favorite places to stay in Miami. The location in Brickell is hard to beat. You are right in Brickell City Centre with restaurants, shopping and everything else around you, but once you are inside the hotel it still feels like its own space.
The rooms are modern, spacious and have great views, especially with the floor to ceiling windows and balconies. The pool area is also really well done and feels more like a place you actually want to spend part of the day rather than just a hotel amenity.
One of the best parts is Sugar on the rooftop. The views from the 40th floor, especially around sunset and at night, are incredible and it is nice being able to have one of Miami’s better rooftop spots without even leaving the hotel.
The staff were great throughout the stay and everything felt easy. If you want to stay in Brickell and be walking distance from a lot of what Miami has to offer, while still having a hotel that feels stylish and comfortable enough to enjoy on its own, EAST is a great choice.
Reviewed on Sep 24, 2026
Shore View Hotel
Hollywood Beach
CA $1,427
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (49 reviews)
Room was not clean- kitchen sink in particular was filthy. Check in was terrible- no one at the office, stood outside for 45 mins waiting for someone to answer the phone. Would not stay here again.
Reviewed on Apr 27, 2026
The Penguin Hotel
South Beach
CA $987
per person
Dec 9 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very good! (1,963 reviews)
They let us check in a little early, and watched our bags all day after we checked out.
Reviewed on Sep 23, 2026
Monroe County Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
CA $181
CA $306 total
Oct 4 - Oct 5
includes taxes & fees
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $209
CA $314 total
Sep 29 - Sep 30
includes taxes & fees
9.2/10 Wonderful! (1,781 reviews)
"Very nice property even though they have some remodeling going on, the place is agreeable. The staff in general was amazing, at least my experience was great. I visited the place few days after an accident with some limitations and my mother, an elderly person, they went an extra step to assist us ..."
Reviewed on Sep 24, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $167
CA $267 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (2,681 reviews)
"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate ..."
Reviewed on Sep 23, 2026
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 $856, 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
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.
Florida Keys Beaches
8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
Southernmost Point
8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
Mallory Square
9.2/10 (15,939 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
Sombrero Beach
9.0/10 (2,464 reviews)
Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.
Smathers Beach
8.4/10 (8,320 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
Dry Tortugas National Park
8.8/10 (2,184 reviews)
Separated from the mainland and encased by golden beaches and colorful coral reefs, this is a national park of fascinating ocean scenery.
Ernest Hemingway Home and Museum
9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
What to do in Monroe County
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
CA $59
per adult
94% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
CA $109
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
