Key West Vacation Rentals

Key West Winter Rentals: Best Vacation Homes 2023

Key West Winter Rentals

A Diverse Family Enjoys A Sunny Day On A Key West Beach Surrounded By Colorful Beach Houses.

Key West Winter Rentals: With its balmy weather and vibrant culture, Key West is a popular winter destination. Our article navigates you through monthly rentals in this tropical paradise, helping you find a home away from home.

Key Takeaways

  • Key West offers a variety of monthly vacation rentals, including villas, cottages, condos, and historic homes.
  • Popular rental platforms in Key West include VRBO and
  • Renting a monthly vacation home in Key West allows you to live like a local and enjoy more space and amenities than hotels.
  • You can save money and fully embrace the island lifestyle by choosing a monthly rental instead of a hotel for an extended stay in Key West.

Key West Monthly Vacation Rentals

A Colorful Beachfront Cottage With Palm Trees, Beach Chairs, And A Bustling Atmosphere.

Key West offers a variety of rental options for those looking for monthly vacation rentals, ranging from condos to private homes.

Variety of rental options

Key West Monthly Vacation Rentals opens a world of options for winter visitors. They can pick from different kinds of homes.

  1. Villas: These offer more space and luxury for groups or large families.
  2. Cottages: A cozy option for smaller families or couples who want a private haven.
  3. Condos: These are a good choice for those who seek modern comforts in compact spaces.
  4. Historic homes: These historic old houses are just right for those who love charm and character.
  5. Pet-friendly properties: Animal lovers won’t have to leave their furry friends behind with these pet-friendly options.
  6. Homes with private docks: Waterfront homes such as this one are Ideal for boating enthusiasts or anglers.

Key West Snowbird Rentals

A Picturesque Beach Cottage With A Hammock And Palm Trees, Featuring Various People And Their Different Styles And Outfits.Snowbird rentals in Key West are the perfect option for those seeking long-term stays and the chance to embrace the island lifestyle fully.

Ideal for long-term stays

A Vibrant Street In Key West With Colorful Houses, Lush Vegetation, And Diverse People In Different Styles, Showcasing A Bustling Atmosphere.

Key West Snowbird Rentals are fit for long stays. You can rent a home for at least a month or up to six months. This is great if you want to live on the island and feel it’s best for over a few days.

The longer stay lets you sink into Key West’s vibrant culture truly. Take your time, and enjoy the sun, palms, and ocean – they have no rush!

Enjoying the island lifestyle

A Photograph Of A Hammock Between Two Palm Trees On A White Sandy Beach, Featuring Diverse People Enjoying Themselves.

Key West offers a unique, laid-back island lifestyle perfect for winter vacationers. With its warm weatherstunning beaches, and vibrant culture, Key West allows you to escape the cold and fully immerse yourself in a tropical paradise.

From sipping cocktails at beachside bars to exploring coral reefs through water sports activities, there are plenty of opportunities to relax and have fun. Whether enjoying the beautiful scenery or indulging in delicious seafood cuisine, Key West embodies the essence of an island getaway.

So why not embrace the island lifestyle during your winter vacation?

Benefits of Key West Monthly Rentals

A Stylish Living Room With A View Of The Ocean, Showcasing Different People, Hairstyles, And Outfits.

Key West monthly rentals offer the opportunity to live like a local, with more space and amenities than hotels and cost savings for extended stays.

Living like a local

Why not live like a local when staying in Key West for the winter? Vacation rentals provide the perfect opportunity to immerse yourself in the local culture and lifestyle. Instead of being confined to a hotel room, you’ll have your own space with all the amenities of your home.

You can shop at local markets, cook meals in your well-equipped kitchen, and explore the neighborhood just like a resident. With Key West monthly rentals, you can truly experience what it’s like to be part of this vibrant community.

More space and amenities compared to hotels

A Luxurious Vacation Rental With A Spacious Living Room, Well-Equipped Kitchen, Private Pool, And Stylish Interior Design.

Key West vacation rentals offer more space and amenities compared to hotels. Instead of a small hotel room, you can have an entire house or condo to yourself! Imagine having a spacious living room, a well-equipped kitchen, and even your private pool or hot tub.

Vacation rentals allow you to spread out and make yourself home while on vacation. Plus, many rentals come with added extras like high-speed internet, air conditioning, and beautiful views of the ocean or tropical gardens.

You’ll have all the comforts of home in your private paradise. So why settle for a cramped hotel room when you can have so much more space and amenities with a Key West vacation rental?

Cost savings for extended stays

If you plan to stay in Key West for an extended period during the winter, opting for a monthly vacation rental can help you save money. Accommodations in Key West cost around $172 per night, but if you rent a house, the average price goes down to about $949 per night.

This means that you can significantly reduce your overall costs by choosing a monthly rental instead of staying at a hotel. Plus, many rental property owners are flexible with pricing, especially during the off-season.

So if you want to enjoy an extended winter getaway in Key West while saving some cash, consider booking a monthly vacation rental.

Finding the Perfect Key West Monthly Rental

A Photo Of A Beach Cottage With Different People, Hairstyles, And Outfits, Surrounded By Palm Trees And A Bustling Atmosphere.

When searching for the perfect Key West monthly rental, consider using online platforms or working with a rental agency to find a property that meets your needs and preferences.

Online rental platforms

A Diverse Family Enjoying Their Time Together In A Spacious Vacation Rental Living Room.

Are you looking for a Key West monthly rental? You can find the perfect place to stay by using online rental platforms. Here are some options to consider:

  1. Vacation Homes of Key West: They offer a wide selection of monthly vacation rental homes, villas, cottages, and condos in Key West.
  2. Vacasa: This platform manages vacation rentals across the United States, including Key West. You can find a variety of options to suit your needs.
  3. Cozycozy: A website that allows you to search for vacation rentals, Airbnb listings, bed and breakfasts, and hotels. They have a large selection of accommodations available.
  4. AvantStay: If you’re looking for a tropical living experience, their Key West homes provide just that. They offer vacation rentals, beach houses, and ski resorts.
  5. Key West Monthly Rentals: This specific rental platform specializes in long-term stays in Key West. They have options tailored specifically for extended vacations.

Working with a rental agency

Are you planning a winter vacation in Key West? If so, working with a rental agency is the way to go. Vacation Homes of Key West offers a variety of monthly vacation rentals, including cottages, villas, condos, and estates.

They allow you to live like a local during your stay. Whether you’re looking for a cozy cottage or a luxurious estate, they have options that cater to different preferences and budgets.

Vacasa is another reputable rental management company that professionally manages vacation rentals across the United States. So when it comes to finding the perfect place for your winter getaway in Key West, working with a rental agency will make your search easier and ensure you find the ideal home away from home.

Considerations when choosing a rental property

  1. Location: Choose a rental property that is conveniently located close to attractions and activities in Key West, such as the beach, Duval Street, or Mallory Square.
  2. Amenities: Check what amenities are included in the rental, such as a pool, private dock, or pet-friendly options if necessary.
  3. Size and Space: Consider the size of the rental property to ensure it can comfortably accommodate your group or family.
  4. Budget: Set a budget for your winter vacation rental and find options within your price range.
  5. Reviews: Read reviews from previous guests to get an idea of the quality and experience provided by the rental property.
  6. Rental Policies: Familiarize yourself with the terms of service and any restrictions or regulations set by the rental property owner or management company.
  7. Security: Ensure the rental property has proper security measures for peace of mind during your stay.
  8. Communication: Look for responsive and helpful rental managers or agencies who can assist you during your stay if any issues arise.

Consider all these factors when choosing a winter vacation rental in Key West to make the most of your stay on this tropical paradise island!

Exploring Key West During the Winter

A Vibrant Sunset Over A Beach With Palm Trees, Featuring Diverse People And A Bustling Atmosphere.

Key West is the perfect destination for a winter getaway with its mild winter weather, festive events, and endless outdoor activities. Discover the tropical paradise waiting to be explored!

Mild winter weather

A Vibrant Sunset Over A Serene Beach In Key West Featuring Diverse People And Stunning Photography.

Key West is famous for its mild winter weather, making it the perfect destination for your winter vacation. During this time, temperatures reach the upper 70s during the day and drop to the upper 60s at night.

With dry and sunny days and refreshing ocean breezes, you can enjoy outdoor activities and explore everything Key West has to offer comfortably. Whether it’s strolling along sandy beaches or indulging in water sports, you’ll find that Key West’s mild winter weather creates an enjoyable experience for your vacation.

Festivals and events

Key West is known for its parties and festivals during the winter season. Here are some of the exciting events you can experience in Key West:

  1. Fantasy Fest: This popular festival features costumes, body painting, music, parades, and various activities. It’s a vibrant and colorful celebration that brings together locals and visitors.
  2. Holiday Fest: Key West hosts this festival, offering a magical Christmas experience. You can enjoy festive decorations, live performances, and even meet Santa Claus himself.
  3. Lighted Boat Parade: Witness the annual Lighted Boat Parade, where boat owners decorate their vessels with sparkling lights and festive decorations. It’s a unique sight to behold as the boats cruise through the waters of Key West.

Outdoor activities and attractions

Key West offers a variety of outdoor activities and attractions during the winter months.

  • Visitors can enjoy snorkeling in the coral reefs off the coast of Key West.
  • You are exploring Fort Zachary Taylor Historic State Park, where you can hike, swim, and relax on the beach.
  • We were taking a guided tour on the Conch Train to learn about the history and culture of Key West.
  • Walking or taking a trolley tour is a great way to experience the local culture and sights.
  • The Key West Butterfly and Nature Conservatory is a must-visit for nature lovers, with hundreds of colorful butterflies.
  • The Audubon House and Tropical Gardens offer a peaceful escape with beautiful gardens and historic architecture.
  • For garden enthusiasts, don’t miss the Key West Garden Club, located in a former military fort.
  • There are 17 things to know before visiting Key West to help you plan your trip better.
  • You can find a list of the best things to do in Key West in winter for more ideas on how to spend your time.
  • Outdoor activities such as kayaking, stand-up paddleboarding, fishing charters, and diving on the reefs are readily available in the Keys.


A Stunning Photo Of A Luxurious Beachfront Villa With Palm Trees And Crystal Blue Waters, Featuring People Of Different Ethnicities And Outfits.

In conclusion, Key West is a fantastic destination for winter rentals. With various options available, including monthly vacation and snowbird rentals, visitors can enjoy the island lifestyle and all Key West offers. Key Largo is another great option for a quieter winter vacation. Key Largo is home to one of our favorite winter vacation hotels, Bakers Cay.

Whether it’s the mild winter weatherfestivals and events, or outdoor activities and attractions, there’s something for everyone in this tropical paradise. So why wait? Start planning your winter getaway to Key West today!


1. How much does renting a winter vacation home in Key West cost to rent?

The cost of renting a winter vacation home in Key West is influenced by various factors such as the location, whether it has an ocean view or a beautiful condo, size, and amenities such as private pools and high-speed internet. Checking with local property management companies or websites like VRBO or Airbnb for specific pricing is a wise choice.

2. Are utilities included in the rental price for Key West winter rentals?

Usually, utilities such as electricity and water are covered in the rental price for Key West winter rentals. However, connecting with the property manager to confirm this is recommended.

3. Can I bring my pet to a Key West winter rental?

Pet-friendly rentals exist in Key West. Some allow pets, while others may impose restrictions. Before planning a stay, always ask about the pet policy.

4. How do I book a Key West winter rental?

Book a Key West winter rental can be done directly through the property owner or online platforms specializing in vacation rentals. Key West rentals are abundant, and these platforms offer easy access to options.

5. What are some popular options for Key West winter rentals?

Private Homes and Condos

Private homes and beautiful condo options offer a quiet neighborhood setting and may come with private pools or ocean views. Historic Key West Vacation Rentals is an excellent source.

Location Benefits

Rentals in Old Town Key West, Truman Annex, and Duval Square are within walking distance of great places and good food. Ocean views, palm trees, and boat docks enhance these locations.

Amenities and Extras

Look for rentals with a swimming pool, tennis court, or golf course near Key West Golf Club. Weekend getaway spots might include front porch settings, gorgeous home designs, and full kitchens.

Special Locations

Consider staying near the Southernmost Point, Smathers Beach, or South Beach. Rentals close to the Dolphin Research Center, Hemingway Home, or the Studios of Key West add a unique touch.

Additional Considerations

Strict city regulations in Key West might affect rental terms of use. Rentals in gated communities like the Key West Golf Club or those with easy access to overseas highways provide additional benefits. Don’t forget to savor some key lime pie!

6. Are there any unique rentals in Key West?

Yes, there are! From historic home options to French doors and large group accommodations, Key West vacations are filled with a wide range of beautiful Florida Keys vacation rentals, including mobile homes and condo units. Some might even offer keyboard shortcuts for convenience.


  • What is the best time to book a rental? The best vacation rentals might be available during specific seasons. Contact a local property management company to inquire.
  • Are there options for a short drive to popular spots? Rentals near the Lower Keys or the heart of Key West offer short drives to popular spots, including Higgs Beach Dog Park.

Key West provides an ideal vacation spot with many options for every traveler. Whether seeking a great location near natural habitat centers or a perfect home with luxurious amenities, your winter vacation in Key West is an unforgettable experience!

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