Monroe County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Monroe County

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

Key West

Key West

Top hotels in Monroe County

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is 3.822.780 ₫ per night from 25 Aug to 26 Aug
3.822.780 ₫
6.225.044 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (3,489 reviews)
"My overall stay at the hotel was good, except for one major issue. I arrived around 12:00 PM, but check-in time is typically at 4:00 PM. The hotel receptionist informed me that my room was available; however, I could only check in early if I paid a $50 fee. I asked for clarification on the fee and ..."

Reviewed on 27 Jul 2026

Southernmost Beach Resort and Guesthouses
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 3.076.487 ₫ per night from 18 Aug to 19 Aug
3.076.487 ₫
5.977.453 ₫ total
18 Aug - 19 Aug
includes taxes & fees
8.6/10 Excellent! (2,384 reviews)
"I was very disappointed with our stay. The elevator didn't work during our visit, which made carrying luggage a real hassle. We stayed for three nights and never received fresh towels. Housekeeping never cleaned our room the entire time, which is not what you expect when staying at a resort. The ..."

Reviewed on 27 Jul 2026

Beachside Resort & Residences
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 5.236.685 ₫ per night from 11 Aug to 12 Aug
5.236.685 ₫
7.815.687 ₫ total
11 Aug - 12 Aug
includes taxes & fees
Cheeca Lodge & Spa
See all 8,299 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 holiday package cost?
Our Monroe County holiday packages, which start at just , 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 1null000null000 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 holiday?
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 holiday package?
With a holiday 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 holiday package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Booked your Monroe County holiday 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 beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says holiday like spending a care-free day in Florida Keys Beaches, a popular beach in Long Beach Estates.
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