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.
Plunge Beach Resort

Plunge Beach Resort

3.5 out of 5
Price was CA $1,841, price is now CA $1,017 per person
CA $1,017
per person
Oct 25 - Nov 2
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (1,188 reviews)
Overall, the resort was decent but had some drawbacks. The staff was friendly and accommodating, but the cleanliness of the property and rooms was just alright—not as great as expected. Unfortunately, our original room had no hot water, and we weren’t made aware of this until the next day, after we had already gone through cold showers. Once the issue was acknowledged, we were moved to another building where hot water was available, but the new room did not have the same pool access as our original booking, which was a bit disappointing. The room itself was fine, but nothing particularly special. With a little more attention to communication and upkeep, the experience could have been much smoother.

Reviewed on Aug. 16, 2025

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 $23,847, price is now CA $11,049 per person
CA $11,049
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $2,847, price is now CA $1,362 per person
CA $1,362
per person
Oct 25 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
Really nice location and staff. Valet service sucked.

Reviewed on Aug. 22, 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was CA $2,945, price is now CA $1,466 per person
CA $1,466
per person
Oct 25 - Nov 2
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2,500 reviews)
First time there. Definitely will return.

Reviewed on Aug. 19, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $7,954, price is now CA $4,253 per person
CA $4,253
per person
Nov 1 - Nov 8
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,265 reviews)
Incredible service and friendly staff. Will definitely be back!

Reviewed on Aug. 21, 2025

Monroe County Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 25 to Aug 26
CA $173
CA $265 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,474 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on Aug. 20, 2025

Beachside Resort & Residences
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Sep 2 to Sep 3
CA $232
CA $341 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,716 reviews)
"I loved everything about this resort. So clean and easy to navigate our way around. Transportation offered worked well for us."

Reviewed on Aug. 18, 2025

Oceans Edge Key West Resort, Hotel & Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Sep 23 to Sep 24
CA $159
CA $257 total
Sep 23 - Sep 24
includes taxes & fees
9/10 Wonderful! (1,493 reviews)
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled."

Reviewed on Aug. 21, 2025

Chesapeake Beach Resort
See all 8,318 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 $1,017, 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.