Monroe County vacation rentals

We found 7,707 vacation rentals — enter your dates for availability

Select from 5041 houses, 1448 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 cities in Monroe County

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Find out more about Monroe County

Find out more about Monroe County

Why visit Monroe County

  1. Idyllic beaches: Monroe County boasts stunning beaches and picturesque islands, perfect for sunbathing and relaxation.
  2. Outdoor adventures: Enjoy a range of activities like kayaking, snorkeling, and hiking in beautiful national parks.
  3. Charming Key West: Explore the vibrant culture, unique shops, and dining experiences in historic Key West.
  4. Diverse accommodations: Choose from private vacation homes, cozy cottages, and modern condos tailored to your needs.
  5. Rich cultural experiences: Immerse yourself in the local charm and history that Monroe County has to offer.

Popular types of accommodation in Monroe County

If you're planning a getaway to Monroe County, we've got the perfect accommodations for you. Our most sought-after options include houses, cozy cottages, and modern condos. Whether you're looking for a spacious holiday home or a special vacation rental for a romantic retreat, you'll find transparency, savings, and reassurance in our selection. Explore the charm of Monroe County with the ideal stay tailored just for you!

  • Houses: The most sought-after choice for visitors in Monroe County, these homes provide spacious accommodations for families and groups.
  • Condos: A popular second option, condos offer a blend of comfort and convenience, often with stunning views and amenities.
  • Cottages: These delightful, quaint spaces are perfect for a peaceful getaway, ideal for couples or small families.
  • Apartments: A practical option for solo travellers or couples, apartments grant a more urban experience.
  • Villas: Luxurious and spacious, villas are an excellent choice for those seeking a lavish stay.**

Top attractions in Monroe County

Monroe County is perfect for outdoor enthusiasts and beach lovers seeking adventure in the sun. Explore stunning beaches, picturesque islands, and national parks that offer a rich cultural experience. From sightseeing to various outdoor activities, this vibrant region promises an unforgettable vacation filled with natural beauty and local charm. Get ready to immerse yourself in the captivating landscapes and unique attractions that Monroe County has to offer!

  1. Duval Street: Experience the vibrant atmosphere of Duval Street, lined with eclectic shops, lively bars, and cafés. This bustling thoroughfare is the heart of Key West, perfect for people-watching and enjoying the nightlife.
  2. Mallory Square: Known for its stunning sunsets, Mallory Square offers a lively gathering spot with street performers, local artisans, and food vendors, creating a festive vibe with breathtaking views of the Gulf of Mexico.
  3. Southernmost Point: A must-visit symbolic landmark, the Southernmost Point buoy marks the southern tip of the continental U.S. This iconic spot is steeped in culture and offers a fantastic photo opportunity with its vibrant colours.

Things to do recommended for couples

Monroe County offers unforgettable experiences for couples. Dive into adventure at the Florida Keys Dive Center, indulge in luxury at the Florida Keys Country Club, or explore the stunning outdoor activities on Pigeon Key. Each destination promises romance and excitement in the beautiful Florida Keys.

Things to do recommended for families

Families visiting Monroe County, Florida, can enjoy a splashing good time at Jacob's Aquatic Center, relax at the MLK Community Pool, and explore the serene New Mahogany Hammock State Botanical Site for wellness and relaxation amidst nature's beauty.

Things to do recommended for groups

In Monroe County, gather your group for a lively evening at Jimmy Johnson's Big Chill, enjoy a round at the Key West Golf Club, or relax with craft brews at Florida Keys Brewing Co. Experience romance and entertainment amidst the stunning Florida Keys scenery.

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

No matter if you’re travelling with a group, enjoying a family getaway, bringing along your furry friends, or seeking extended stays, be sure to prioritise your preferences in the booking process. 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 gatherings. Luckily, you can easily apply filters for these options and more on Vrbo.
  • Traveling to Monroe County with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with amenities that cater to their age, 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 trip isn’t truly complete without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • 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 effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Monroe County

Monroe County, Florida, offers a tropical paradise perfect for outdoor adventures and beach holidays. Explore charming cities like Key West, where you can unwind in vacation rentals, enjoy family-friendly activities, or indulge in romantic excursions. Surrounded by stunning recreational areas, this destination promises a relaxing atmosphere and unforgettable experiences, ensuring your stay is filled with delightful memories in this beautiful coastal region.

  • Key West: Key West is a vibrant island city, renowned for its stunning sunsets and rich history. Located at the southernmost point of the continental United States, it offers a unique blend of cultural experiences and outdoor activities. Visitors can explore the charming Old Town, where historic architecture meets a lively arts scene. Key West is perfect for families looking to relax on beautiful beaches, shop in eclectic boutiques, or dine at waterfront restaurants. Popular attractions include the Ernest Hemingway Home and Museum and the iconic Mallory Square, where daily sunset celebrations take place.
  • Key Largo: As the first of the Florida Keys, Key Largo is celebrated for its outdoor adventures and natural beauty. This island city is a haven for families and beach enthusiasts seeking sun-soaked days and thrilling water activities. Visitors can snorkel or dive in the John Pennekamp Coral Reef State Park, the first underwater park in the U.S., or relax on the soft sands of its pristine beaches. Key Largo also boasts a variety of shopping areas and resorts, making it an ideal base for exploring the Florida Keys.
  • Marathon: Marathon is an inviting city nestled in the heart of the Florida Keys, known for its family-friendly atmosphere and stunning coastal views. This city offers a plethora of options for outdoor activities, including fishing, boating, and beach lounging. The famous Seven Mile Bridge connects Marathon to other keys, providing scenic drives and breathtaking ocean views. Families can enjoy attractions such as the Dolphin Research Center or the Turtle Hospital, where they can learn about marine conservation efforts while experiencing the charm of island life.

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can really pay off, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To help you discover the perfect Vrbo property that fits your budget, feel free to use our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient hub where you can plan new adventures, refine your existing itineraries, or manage your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: 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 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)
  • The Kite House (1.7 mi / 2.7 km)
  • MLK Community Pool & Community Center (2 mi / 3.2 km)
  • Blue Hole (26.7 mi / 42.9 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 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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