Monroe County Vacation Rentals, Florida: house rentals & more

Select from 4885 houses, 1441 condos, and other vacation rentals to find the perfect place for your stay in Monroe County. Vacation homes provide the best amenities for your family, friends, or furry companion, such as a fireplace and garden. At the end of the day, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Popular Monroe County destinations on Vrbo

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Condo/Apartment

Find the best place to stay - Monroe County

Skipjack Resort & Marina

Sleeps 8 · 1 bedroom

Perfect Choice! With Stunning Views of the Island, Private Beach, Pet-Friendly

Sleeps 2 · 1 bedroom · 1 bathroom

Top rated rentals - Monroe County

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Find the perfect vacation rental for your Monroe County getaway

Learn about the unique charm of Monroe County with a stay in a private vacation home. This city has something for everyone. Duval Street and Everglades National Park are just a couple of the must-sees. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Monroe County

Do you want to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Monroe County a fun spot to vacation. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Key West Golf Club (2.1 mi / 3.4 km)
Blue Hole (26.7 mi / 42.9 km)
The Kite House (1.7 mi / 2.7 km)
MLK Community Pool & Community Center (2 mi / 3.2 km)

Exploring the natural features in Monroe County

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Monroe County. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

Smathers Beach (0.8 mi / 1.4 km)
Clarence S. Higgs Memorial Beach Park (1.3 mi / 2.1 km)
Key West Tropical Forest and Botanical Garden (1.6 mi / 2.7 km)
South Beach (1.8 mi / 2.9 km)
Key West Butterfly and Nature Conservatory (1.9 mi / 3 km)
Southernmost Point (1.9 mi / 3.1 km)

Traveling to and around Monroe County

The nearest airport is in Key West Intl. Airport (EYW), located 1.3 mi (2 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 46.6 mi (75 km) away.

Frequently asked questions

What is the best area to stay in Monroe County when booking a vacation rental?

If you’re visiting Monroe County, Key Largo is among the more desired locations to spend a vacation. While here, pay a visit to leading sights like John Pennekamp Coral Reef State Park and Jimmy Johnson’s Big Chill.

What is the most popular type of vacation rental accommodation in Monroe County?

Condos are the most popular kind of vacation rental in Monroe County, according to our data. Even if you’ve got something different in mind, Vrbo has vacation homes in loads of sizes and shapes. Browse our options to find your perfect Monroe County pad.

How much does it cost to rent a vacation rental in Monroe County?

The average price for a vacation home in Monroe County can vary based on factors like time of year, length of stay and property type. Whether you’re dreaming about a sprawling villa with a pool or a cozy cottage for just you and your sweetheart, just enter your dates of travel to find stays with amazing value.

How much does it cost to rent a beach house in Monroe County?

The average price for a vacation rental near the beach in Monroe County depends on when you’re traveling and the type and size of property you’re searching for. You can find prices easily and quickly on Vrbo by entering the dates you’ll be traveling. Then use our filter tool to select the number of bedrooms and amenities essential to you, like WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Monroe County?

Pack a travel bag and a bone for the pooch in your life because Monroe County has 737 properties that welcome pets with open arms. Let your furriest friend join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check our “Pets allowed” filter box.

Are there large group vacation rentals in Monroe County?

Monroe County has 924 vacation homes that can host 10 or more guests. These properties come with enough space to enjoy good times with family and friends.

Are there one-bedroom vacation rentals in Monroe County?

Monroe County has 883 one-bedroom rentals available. Usually located in well-regarded areas because of their smaller size, a one-bedroom vacation rental is perfect if you’re traveling with a friend or your partner. And with plenty of home comforts like WiFi and more privacy, you’ll be able to chill out while enjoying this top destination.

Can I find two-bedroom vacation rentals in Monroe County?

Gather your family and enjoy a relaxing escape in one of the 2,396 two-bedroom vacation properties Monroe County has to offer.

Are there vacation rentals with WiFi in Monroe County?

Whether you want to keep up with the headlines, send a few emails or post a pic to social media, there are 2,770 vacation homes with WiFi in Monroe County. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.

How can I find vacation rentals with air conditioning in Monroe County?

Decide on your travel dates and then use our filter tool to find vacation rentals with air conditioning in Monroe County on Vrbo. With 5,879 air-conditioned properties available, you can look forward to a comfy and cool stay.

How old do you have to be to rent a vacation rental in Monroe County?

We recommend you check with the Monroe County vacation rental you’re looking at on Vrbo as the minimum age varies. However, typically it’s 16, 18 or 21.

How long can I rent a vacation rental in Monroe County for?

The length of time you can rent a vacation rental in Monroe County varies according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With plenty of features like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you’re sure to find a perfect place to call your home away from home in Monroe County.

Does Vrbo offer discounts for vacation homes in Monroe County?

Short break or extended escape, Vrbo has some excellent value options in Monroe County to match your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the ideal place to stay — without spending a fortune.