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

Key West

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

Key Largo

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

Marathon

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

Islamorada

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

Big Pine Key

Big Pine Key

Top Monroe County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Private Oasis at Arya

Private Oasis at Arya

Coconut Grove
Save 100% on your flight
CA $1,665
per person
Nov 11 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,044 reviews)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $17,541
per person
Dec 20 - Dec 25
found 17 hours ago
Roundtrip non-stop 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

Miami Vacation Rentals - Brickell

Miami Vacation Rentals - Brickell

Brickell
Save 100% on your flight
CA $3,742
per person
Dec 23 - Jan 1
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (570 reviews)
Brickell Arch Apartment City Views & Free Parking by Palermo Home Miami

Brickell Arch Apartment City Views & Free Parking by Palermo Home Miami

Brickell
Save 100% on your flight
CA $2,448
per person
Dec 23 - Jan 1
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
10/10 Exceptional! (4 reviews)
The room was very clean and organized with a wonderful city view. The building was relatively quiet. We especially loved how spacious the bathroom area is. Valet and concierge services are exceptional, the restaurant on the 25th floor is great, and it's in a great location in Miami. However, we did encounter one issue that did cost us a decent amount of money. The water connection for the washer was not hooked up and no dryer was available. This meant instead of being able to do our laundry, we had to buy new clothing items. There was also a feminine hygiene wrapper under the bed upon arrival. These things made me question if the bed sheets or towels were properly laundered. Overall, we enjoyed the experience. We typically stay at the Icon, but due to the construction on that building we chose to try the Arch and will probably do that again.

Reviewed on Jul 6, 2026

Modern Condo Brickell by Palermo Home

Modern Condo Brickell by Palermo Home

Brickell
Save 100% on your flight
CA $1,998
per person
Dec 23 - Jan 1
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7/10 Good! (2 reviews)
The location is in a very ideal place, only a 10 min walk into Brickell City Centre. However, the property was not the best and we had a few issues such as the toilet not working which was fixed. There was also a leak from the sink and we couldn’t find amenities such as the hairdryer and the host stopped replying which has lowered our scoring as that for us is a pretty essential item. There is also building works opposite the property which start around 7/8am each day. Also, when you check out, they charge you $5 per bag to leave your items and also $60 to use the pool which feels very unfair.

Reviewed on Apr 1, 2026

Monroe County Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
CA $241
CA $375 total
Oct 20 - Oct 21
includes taxes & fees
9.2/10 Wonderful! (1,470 reviews)
"Take a large was more than we expected. It was beautiful. It was clean. The service was amazing. The hotel had the perfect keys vibe. The beach was exactly what we needed. Perfect for group of friends families overall great hotel great food. Great drinks great bar service the rooms for spacious clean ..."

Reviewed on Oct 4, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $198
CA $303 total
Oct 18 - Oct 19
includes taxes & fees
Chesapeake Beach Resort
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $298
CA $425 total
Oct 6 - Oct 7
includes taxes & fees
Margaritaville Beach House Key West
See all 8,265 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 $1,665, 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.
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A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.

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.
See properties
A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

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.
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A beach with clear turquoise water, white sand, and palm trees.

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.
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A beach with white sand, palm trees, and a building in the background.

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.
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Fort Jefferson, a brick fort with arched windows and a flagpole.

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.
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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

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.
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What to do in Monroe County

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
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 $78
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 $82
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.