Monroe County vacation rentals

We found 7,799 vacation rentals — enter your dates for availability

Select from 2522 houses, 883 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.

Vacation rentals with weekly discounts - Monroe County

Showing deals for:Jul 17 - Jul 24

Find out more about Monroe County

Why visit Monroe County

  • Stunning Beaches: Monroe County boasts beautiful beaches, perfect for sunbathing and relaxing.
  • Outdoor Adventures: The area offers various activities like hiking and water sports, appealing to adventure seekers.
  • Florida Keys Scenery: Explore the breathtaking landscapes and unique charm of the Florida Keys.
  • Diverse Accommodations: Choose from spacious vacation homes, inviting condos, and cozy cottages for a perfect stay.
  • Cultural Experiences: Immerse yourself in the local culture with unique events and attractions throughout the region.

Popular types of accommodation in Monroe County

If you're exploring vacation rentals in Monroe County, you're in for a treat. Our diverse offerings include spacious houses, inviting condos, and cozy cottages that cater to all your needs. Whether you're seeking the best vacation rentals for a family getaway or a romantic retreat, we have the perfect accommodations for you. Enjoy transparency and savings while finding your ideal home away from home in this beautiful region.

  • Houses: The top choice for travelers in Monroe County, these homes offer spacious and comfortable stays for families or groups.
  • Condos: A close second, condos provide a blend of convenience and amenities, perfect for couples or small families.
  • Cottages: Ideal for those seeking a quaint and charming retreat, these cottages add a touch of coziness to your getaway.
  • Apartments: A practical option for visitors, apartments offer flexibility and ease during your stay.
  • Villas: For a luxurious experience, villas present upscale accommodations with stunning views.**

Top attractions in Monroe County

Monroe County, Florida, is perfect for outdoor enthusiasts and beach lovers seeking adventure. With stunning beaches, beautiful islands, and national parks, there’s much to explore. Visitors can enjoy a variety of cultural experiences while sightseeing around the area, making it an ideal destination for those looking to immerse themselves in nature and local culture. Whether lounging on the beach or hiking through parks, Monroe County offers something for everyone.

  • Duval Street: A vibrant thoroughfare filled with shops, restaurants, and nightlife, Duval Street embodies the lively spirit of Key West. Explore its eclectic mix of local artists, street performers, and enticing eateries that create a bustling atmosphere.
  • Southernmost Point: This iconic landmark marks the southernmost point in the continental U.S. Take a photo with the famous buoy and soak in the rich history and culture of the area, surrounded by stunning ocean views.
  • Mallory Square: Known for its nightly sunset celebration, Mallory Square is a lively gathering spot where locals and tourists enjoy street performers, artisans, and breathtaking sunset views over the Gulf of Mexico.

Things to do recommended for couples

For a romantic getaway in Monroe County, explore Pigeon Key's adventurous watersports, dive into the vibrant underwater world at Florida Keys Dive Center, or indulge in luxury at the Florida Keys Country Club. Each activity promises memorable moments together in this tropical paradise.

Things to do recommended for families

Your family will have a blast at Jacob's Aquatic Center, enjoy fun at MLK Community Pool & Community Center, and unwind at the New Mahogany Hammock State Botanical Site, perfect for relaxation and wellness amidst the beautiful scenery of Monroe County.

Things to do recommended for groups

In Monroe County, your group can unwind at Jimmy Johnson's Big Chill for a lively atmosphere, enjoy a round at Key West Golf Club amidst beautiful outdoor settings, and taste local brews at Florida Keys Brewing Co., perfect for a fun-filled, memorable experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Monroe County

If you're planning a trip with friends, family, pets, or looking for extended stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Monroe County with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Monroe County with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Monroe County: For many, a family vacation wouldn’t be the same without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Monroe County: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Monroe County

Monroe County, Florida, offers a delightful blend of outdoor adventures and beach vacations, perfect for families and couples alike. Explore the stunning Florida Keys scenery while soaking up the sun on Key Colony Beach. With a variety of vacation rentals available, you can find the ideal spot to unwind and create lasting memories in this tropical paradise. Whether you're seeking relaxation or thrilling excursions, Monroe County has something for everyone to enjoy.

  • Key West: Key West is a vibrant city located at the southernmost point of the continental United States, surrounded by the turquoise waters of the Gulf of Mexico. Known for its lively atmosphere, this tropical paradise offers a unique blend of cultural experiences, including historic sites like the Ernest Hemingway Home and Museum. Travelers can indulge in shopping at local boutiques or relax at family-friendly beaches. Key West's bustling nightlife and delicious seafood restaurants ensure a memorable visit for all ages, making it an ideal destination for family, business, or leisure travellers.
  • Marathon: Marathon is a charming city in the heart of the Florida Keys, known for its beautiful beaches and outdoor recreational opportunities. This family-oriented destination is perfect for those seeking adventure and relaxation, with an array of water sports such as fishing, kayaking, and snorkeling. Visitors can explore the stunning Seven Mile Bridge or enjoy a day at the beach with the family. Marathon also boasts excellent dining and shopping options, making it a fantastic base for exploring the surrounding Keys while experiencing the warm hospitality of this close-knit community.
  • Key Largo: Key Largo, the first of the Florida Keys, is renowned for its exceptional outdoor experiences and stunning natural beauty. This island city is a haven for families and beach enthusiasts, offering access to world-class diving and snorkeling at John Pennekamp Coral Reef State Park. Explore the lush landscapes, relax on pristine beaches, or visit the local shops and restaurants for a taste of island life. Key Largo's welcoming atmosphere and diverse activities make it the perfect spot for an unforgettable vacation immersed in nature and family fun.

Booking with Vrbo is a breeze

Are you hoping to save some money on your upcoming adventure? Being open to flexible travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. Happy travels.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform to plan new adventures, keep track of your arrangements, or assess and manage your bookings. The properties you’ve saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, simply head over to: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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 Florida Keys Beaches 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:

  • Florida Keys Beaches (14.1 mi / 22.7 km)
  • 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)
  • Simonton Beach (1.7 mi / 2.7 km)
  • South Beach (1.8 mi / 2.9 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 heading to Monroe County, Key West is among the most desired locations to stay. While you're here, explore leading sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.
What is the most popular type of vacation rental accommodation in Monroe County?
The most sought-after types of vacation rentals in Monroe County are houses. After something a little different? Vrbo has a variety of options to match the needs of our guests, so you'll see properties in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Monroe County?
Length of stay, property type and season are some of the conditions that can affect the price of a vacation home. Simply enter your dates of travel to find your perfect escape. From quaint country cottages to expansive luxury villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Monroe County?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Put in your Monroe County travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use the filters to select the features and amenities you want in your vacation home.
What are popular rental amenities in Monroe County?
When it comes to rental amenities that people search for in Monroe County, a microwave oven, a fridge and off-street parking options are the most popular. With Vrbo vacation rentals, there are choices to match your taste and style, whether you're traveling with your partner, your family or even pets.
Are there large group vacation rentals in Monroe County?
With 718 properties that can host 10 people or more in Monroe County, you don't have to cross anyone off the invite list. From family get-togethers to events like birthday and Christmas parties, Vrbo can help you find a large group rental that fits the occasion.
What are the top attractions for families in Monroe County?
Keeping the kiddos entertained during your Monroe County vacation is child's play with these cool family-friendly attractions:

  • Smathers Beach
  • Mallory Square
  • Duval Street

Can I find two-bedroom vacation rentals in Monroe County?
Take off with your besties and enjoy total privacy and comfort in one of the 2,281 two-bedroom vacation properties Monroe County has to offer.
Are there vacation rentals with WiFi in Monroe County?
You'll have a choice of 2,152 vacation rentals with WiFi in Monroe County. If you want to disconnect from the world while on vacation, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Monroe County?
We advise checking with the Monroe County vacation property you want on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Monroe County for?
How long you can rent a vacation rental in Monroe County varies according to the property. Just enter your preferred dates to display a list of options offering extended stays. With a range of amenities such as washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Monroe County.

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