Key West, Florida Vacation Rentals: Condos, Beach Houses, Classic Cottages, & More

Key West, Florida Vacation Rentals: Condos, Beach Houses, Classic Cottages, & More

Key West, Florida, is a tropical hideaway known for its vibrant culture, architecture, clear-blue waters, and historic charm. When it comes to lodging, the options are as diverse as the island itself. Key West vacation rentals offer a range of accommodations to suit every traveler's needs, from beachfront condos with breathtaking views to homey cottages in the heart of Old Town. Whether you're searching for elaborate homes for rent in Key West, Florida, or a simple condo, the choices are never-ending. Browse our wide variety of properties guaranteed to make your stay comfortable and memorable, all while experiencing the laid-back island life of Key West.

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Explore Vacation Rentals in Key West, Florida

Key West, Florida, is a picturesque island paradise in the Florida Keys, known for its historic charm, vibrant culture, stunning tropical landscapes, and unmatched romantic appeal. When you're planning a visit, our Key West rentals provide a variety of accommodation options to make your stay an unforgettable one. Experience the island's unique charm by checking in to one of the condos for rent in Key West in the heart of Old Town, where historic architecture and lively streets define the area, or stay close to Duval Street for bustling nightlife. Alternatively, enjoy the tranquility of true beachfront living, where you can wake up to the soothing sound of waves as they hit the white, sandy shore.

Your Guide to Key West

    What to do in Key West, Florida

  • Known for its laid-back atmosphere, stunning sunsets, and vibrant culture, Key West offers a wealth of activities, making it a well-sought-after destination for travelers. Start by exploring the fascinating history of the island at the Ernest Hemingway Home and Museum, then make your way through the vibrant arts scene at the Studios of Key West, which hosts seasonal exhibitions, workshops, and live performances, or dive into the island's diverse aquatic life and see how many species of fish and types of coral you can spot while snorkeling. With its mix of cultural attractions, natural beauty, and ocean adventures, Key West ensures a memorable vacation for all. If you need a few ideas to help you plan your itinerary, here are our top 3 things to do while you're there:

    Visit the Ernest Hemingway Home and Museum: One of Florida’s most famous historical attractions, explore the former residence of the iconic author and get a glimpse into his life. The property is not only historically significant but also home to the famous polydactyl cats, descendants of Hemingway's own feline companions.

    Enjoy a Sunset Celebration at Mallory Square: Join the nightly festivities at Mallory Square to witness one of the most breathtaking sunsets in the world. Street performers, local vendors, and live music create a festive atmosphere as the sun dips below the horizon.

    Fall in love with the Key West Butterfly and Nature Conservatory: Step into a tropical paradise and wander amidst thousands of exotic butterflies in a lush garden. It's a serene and enchanting experience for nature enthusiasts and families.

  • Best Time to Visit Key West, Florida

  • Key West is a destination that welcomes visitors year-round, so the best time to visit depends on your preferences for weather and crowds. A great time to visit Key West, Florida is during the Spring when the rush of the winter crowds start to taper off, and the weather becomes similar to winter's blissfully mild climate. Speaking of winter, December to February tends to be the busiest time of year, thanks to its day-long sunshine and exciting seasonal events like the Key West Food and Wine Festival. If you’re impartial to some crowds, Summer is also a busy time of year, and with hot and humid weather in the forecast, there’s no better way to cool off than the beach. Rental homes in Key West Florida are usually more affordable during the Fall due to the higher levels of rainfall; however, don’t let that deter you from this city's charm.

  • The Weather in Key West, Florida

  • Key West, Florida, has an enviable tropical climate with warm temperatures all year round –even in the Winter! So if you aren't a huge fan of colder climes, Key West is the place for you with warm Winters ranging from the mid-60s to 70°F (15 - 21°C). Fall temperatures between the mid-70s to low 90s °F (21 -32 °C) make it a great time to enjoy the great outdoors without having to layer up your wardrobe. Spring sees the dawn of the warmer months, and with highs in the 80s°F (26°C), we recommend packing some light, comfortable clothing along with your swimwear. As the Summer creeps in, expect temperatures to range from the mid-80s to the low 90s°F (29-35°C), with high humidity. While there may be the occasional afternoon thunderstorm, you will only need to pack some lightweight clothing, sunscreen, sunglasses, and all the little essentials for keeping cool in the Summer heat.

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Key West Florida Vacation Rental FAQs

  • What are the Different Types of Vacation Rentals in Key West, Florida?

    When planning your trip, explore the diverse rental options available, and choose the one that best matches your vacation style, whether it's a historic house, a modern condo, or a beachfront paradise. With a wide variety of homes for rent in Key West, you're sure to find the perfect property for your island escape.

    Condos are a great choice for families or couples seeking a more self-contained space and the comfort of resort-style amenities such as pools, fitness centers, and waterfront views.

    Key West house rentals offer a wide range of options to suit various preferences and group sizes. Renowned for charming and colorful historic homes, staying in a conch-style home is just one of many vintage Key West house rentals allowing you to experience the traditional architectural style unique to the area. These homes typically feature lush gardens, private pools, and a touch of island history.

    Rental homes in Key West, Florida, come in various sizes and styles, from cozy bungalows to spacious, luxurious estates. These vacation homes provide the comfort and privacy of a house while giving you easy access to some of Key West's main attractions. You can find homes with modern amenities, private pools, and beautiful outdoor spaces for relaxation and entertaining.

    Whatever style and size of vacation rental you select, expect the ultimate tropical getaway in the heart of this vibrant island community.

  • What type of amenities should I expect when booking a house or condo for rent in Key West, Florida?

    You can count on a number of creature comforts and amenities like private pools, outdoor living spaces, fully equipped kitchens, Wi-Fi, and air conditioning. Additionally, many properties provide essential beach gear, like chairs and umbrellas, for a seamless island getaway.

  • What is the best area to stay when traveling to Key West, Florida?

    You can count on a number of creature comforts and amenities like private pools, outdoor living spaces, fully equipped kitchens, Wi-Fi, and air conditioning. Additionally, many properties provide essential beach gear, like chairs and umbrellas, for a seamless island getaway.

  • What is the best area to stay when traveling to Key West, Florida?

    The Old Town area is the most popular and iconic choice for travelers due to its historic charm and proximity to Duval Street and attractions. However, there are many other viable options, including waterfront properties, beachfront condos, and quiet neighborhoods for those seeking a more tranquil escape.

  • How can I get to and around in Key West, Florida?

    You can fly into Key West International Airport (EYW), conveniently located near the city.  Fort Lauderdale–Hollywood International Airport (FLL) is also another option. Once in Key West, public transportation includes the City of Key West's bus system but many travelers prefer renting cars or scooters to give them the freedom to explore the island at a leisurely pace. Taxis and ride-sharing services like Uber and Lyft are also available. Keep in mind that the compact size of the city's Old Town makes it highly walkable, and many attractions are within strolling distance.

  • Are there pet-friendly homes for rental in Key West, Florida?

    Yes, there are many rental homes in Key West Florida that welcome your furry friends. However, some properties have certain restrictions or additional fees, so it’s best to check the details of your chosen property's pet policy before making your reservation.

  • Are there Key West house rentals suitable for groups?

    Yes, Key West offers various options for groups, from spacious rental homes with multiple bedrooms to large waterfront villas. Whether you're traveling with family or friends, you'll find a multitude of rental homes in Key West, Florida to suit your group's size and needs.

  • How much do Key West rentals cost?

    The cost of Key West, Florida vacation rentals varies widely. You can find quaint apartments with nightly prices starting at around $100-200. Luxury waterfront villas or large rental homes can cost $1,000 - $2,000 per night or more.

  • How many Key West rental homes are available?

    There are typically hundreds of Key West vacation rental options, including houses, condos, and quaint cottages, to choose from in this popular tourist destination.