Monroe County vacation rentals

We found 7,783 vacation rentals — enter your dates for availability

Select from 2467 houses, 943 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:Jun 12 - Jun 19

Find out more about Monroe County

Why visit Monroe County

  • Stunning Beaches: Relax on beautiful beaches and enjoy water activities in Monroe County's tropical paradise.
  • Outdoor Adventures: Explore expansive national parks offering hiking, kayaking, and wildlife viewing opportunities.
  • Charming Islands: Discover the unique charm of the Florida Keys, including Key West and its vibrant culture.
  • Vacation Rentals: Choose from a variety of vacation rentals, from cozy cottages to luxurious homes, catering to every traveler.
  • Exciting Excursions: Engage in thrilling excursions like snorkeling, fishing, and eco-tours to enhance your experience.

Popular types of accommodation in Monroe County

Monroe County offers a diverse selection of vacation rentals, perfect for every traveler. Whether you're seeking a spacious private vacation home, a cozy cottage, or a stylish condo, there's something for everyone. Enjoy the convenience of pet-friendly options, or find the best vacation homes to suit your needs. Long Key vacation rentals provide a unique escape, ensuring you have the ideal base for your adventures. Explore your options and make lasting memories in Monroe County.

  • Houses: The top choice for visitors to Monroe County, these homes offer spacious accommodations perfect for families or groups looking for privacy and comfort.
  • Condos: A popular option, condos provide modern amenities and often stunning views, ideal for those wanting a blend of social and private space.
  • Cottages: These quaint and charming retreats are perfect for a cozy getaway, ideal for couples or small families.
  • Apartments: Convenient and often centrally located, apartments are great for travelers seeking a home-like atmosphere during their stay.
  • Villas: Luxurious and spacious, villas offer upscale living with beautiful surroundings, perfect for a lavish vacation experience.**

Top attractions in Monroe County

Monroe County, Florida, is an ideal destination for outdoor enthusiasts and beach lovers seeking adventure and relaxation. With its stunning beaches, charming islands, and expansive national parks, there's no shortage of activities to explore. Whether you're interested in outdoor adventures or cultural experiences, Monroe County offers a diverse range of attractions that will make your vacation unforgettable.

  • Duval Street: Known for its vibrant atmosphere, Duval Street is the heartbeat of Key West, lined with lively bars, restaurants, and shops. Experience the eclectic mix of the city's culture while enjoying street performances and local art.
  • Southernmost Point: A must-visit landmark, the Southernmost Point buoy marks the southern tip of the continental U.S. Capture a photo with this iconic symbol while soaking in the local history and culture surrounding the area.
  • Mallory Square: Famous for its sunset celebrations, Mallory Square offers a lively gathering place featuring street performers, artisans, and food vendors. Enjoy the stunning views of the sunset over the Gulf of Mexico as you mingle with locals and fellow travelers.

Things to do recommended for couples

For a romantic getaway in Monroe County, explore the thrilling water sports at Pigeon Key, dive into adventure with Florida Keys Dive Center, or unwind in luxury at Florida Keys Country Club. Each experience is perfect for couples looking to create unforgettable memories together.

Things to do recommended for families

Your family vacation in Monroe County, Florida, promises fun at Jacob's Aquatic Center and the MLK Community Pool & Community Center, offering vibrant family atmospheres. For a serene experience, unwind at the New Mahogany Hammock State Botanical Site, perfect for relaxation and wellness.

Things to do recommended for groups

Experience the lively atmosphere at Jimmy Johnson's Big Chill, perfect for socializing. Tee off at the scenic Key West Golf Club for some outdoor fun, and unwind with craft brews at Florida Keys Brewing Co., where entertainment and romance blend seamlessly.

*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 a group, family, pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Monroe County with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Monroe County with young kids: Traveling with young kids can be quite a task. 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 family-friendly attractions.
  • Taking your pets with you to Monroe County: For many families, a vacation wouldn’t be the same without their furry companions. If you resonate with this, take a look at Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your pets feel just as comfortable as you do.
  • Planning for a long term stay visiting Monroe County: If you're searching for vacation rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can quickly discover and save on monthly rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Monroe County

Monroe County, Florida, offers a delightful blend of adventure and relaxation, making it an ideal vacation spot for families and couples alike. Explore the stunning beaches, embark on exciting excursions, and enjoy the tropical atmosphere of this coastal paradise. With charming neighborhoods and outdoor activities, you'll find the perfect getaway to unwind and create lasting memories in this beautiful region of the Sunshine State.

  • Key West: As the southernmost city in the continental United States, Key West is an island paradise known for its vibrant culture and stunning sunsets. This lively city offers a perfect mix of family-friendly attractions and city-themed experiences. Visitors can explore the famous Duval Street for shopping and dining, while the local beaches provide opportunities for relaxation and water sports. Notable landmarks include the Hemingway House and the picturesque Mallory Square, where you can witness breathtaking sunset celebrations.
  • Marathon: Located in the heart of the Florida Keys, Marathon is a city that promises outdoor adventures and family fun. Known for its beautiful beaches and a charming tourist precinct, it’s an ideal destination for those seeking sun-soaked relaxation or exciting water activities like snorkeling and fishing. The city boasts a variety of shopping areas and resorts, ensuring a comfortable stay for families. Don’t miss the opportunity to visit the Dolphin Research Center or take a scenic drive across the iconic Seven Mile Bridge.
  • Key Largo: Renowned for its stunning natural beauty, Key Largo is another gem in Monroe County, celebrated for outdoor and beach experiences. As the first of the Florida Keys, it is a gateway to the John Pennekamp Coral Reef State Park, where snorkeling and diving enthusiasts can explore vibrant coral reefs teeming with marine life. With family beaches and shopping areas, Key Largo offers a laid-back atmosphere perfect for relaxation. Visitors can also enjoy kayaking in the mangroves or take a boat tour to see the famous Christ of the Abyss statue submerged in the ocean.

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, opting for a longer stay often results in even greater savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner comes with its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board feature is designed to enhance your travel planning experience. It offers a dedicated space where you can create new trips, pick up from where you last stopped, and manage your travel plans effortlessly. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/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. 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)
  • Simonton Beach (1.7 mi / 2.7 km)
  • South Beach (1.8 mi / 2.9 km)
  • Key West Butterfly and Nature Conservatory (1.9 mi / 3 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.

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