Florida Keys Vacation Rentals

North Key Largo to Key West

Florida Keys Vacation Rentals By Owner

Escape to the tropical paradise of the Florida Keys with our exclusive vacation rentals by owner. From waterfront villas to island retreats, explore our curated selection and secure your ideal accommodation in this sun-soaked archipelago, where turquoise waters and swaying palms set the stage for an unforgettable getaway. Start searching below.

Summerland Breeze: 28 NIGHT MINIMUM! CHECK OUT OUR JUNE SPECIAL! A three-house resort style getaway in the Florida Keys

Summerland Key Vacation Rentals


Islamorada Vacation Rentals
6/BR 6.5/BA SLEEPS 14

Luxury High End Islamorada Private Sandy Beach Access Hammocks, Kayaks, & More!

Islamorada Vacation Rentals

Gorgeous Updated Condo in Oceanfront Building

Islamorada Vacation Rentals

Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft

Islamorada Vacation Rentals

Key Largo Condo with Spectacular Sunset Views

Key Largo Vacation Rentals

Recently upgraded Key Largo Oceanfront Condo with all the toys included

Key Largo Vacation Rentals

Key Largo Ocean Front Villa on the Beach with Incredible views

Key Largo Vacation Rentals

CASA CAYO BY THE SEA ~ Waterfront Paradise

Key Largo Vacation Rentals

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo Vacation Rentals

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo Vacation Rentals

New and first time offered private beach home on the Atlantic Ocean -

Key Largo Vacation Rentals
4/BR 4.5/BA SLEEPS 12

Bahia Azul - Private Sandy Beach - Florida Keys Monthly Vacation Rental

Ramrod Key Vacation Rentals

Gated Ocean front condo with protected boat dock. Immediate access.

Long Key Vacation Rentals

Blue Palms Retreat Vacation Rental

Cudjoe Key Vacation Rentals

Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.

Islamorada Vacation Rentals

Oasis -Oceanfront tropical home with pool and dock

Summerland Key Vacation Rentals

Family Retreat Florida Keys - Perfect for Large Groups - Private Beach and Pool!

Cudjoe Key Vacation Rentals

Florida Keys Vacation Rentals

The Florida Keys are the southernmost point in the USA stretching from Key Largo to Key West it's a scuba diver's, boating and fisherman's dream. Here you can find the sport fishing capital of the world and an abundance of marine life and lively entertainment.

Come and experience the beautiful Florida Keys in your own private rental! From luxurious houses with ocean views to cozy cottages with private pools, you'll find the perfect place to relax and explore the area. Whether you are looking for a one-night stay or a week-long vacation, there are plenty of rentals to choose from.

The selection of vacation rentals offers a variety of sleeping options, from queen beds to bunk beds to pull out couches. You can sleep anywhere from one to nine or more people, making it a great option for large groups or families. Some rentals even have multiple bedrooms and bathrooms, providing extra privacy and comfort.

Take a dip in your own private pool and enjoy the Florida sunshine. Many rentals have outdoor grills and seating areas, perfect for a family cookout. If you're looking for a great view, there are also plenty of beachfront rentals with stunning views of the ocean.

No matter what you're looking for, you'll find the perfect vacation rental in the Florida Keys. With comfortable beds, private pools, ocean views, and more, you'll have everything you need for a relaxing and memorable getaway.

Are the Florida Keys a good place to rent a Vacation Rental?

Yes, the Florida Keys are a fantastic place to rent a vacation rental. This unique archipelago offers a tropical paradise experience with its stunning natural beauty, vibrant marine life, and laid-back island atmosphere. Here are some reasons why the Florida Keys make an excellent choice for a vacation rental and the perfect spot book a Florida Keys rental by owner:

1. Beautiful Beaches and Crystal Clear Waters: The Florida Keys are renowned for their picturesque beaches and crystal-clear turquoise waters. From the white sands of Key West to the secluded coves of Islamorada and Marathon, you'll find a variety of beachfront locations to choose from for your vacation rental.

2. Water Activities and Outdoor Adventures: The Keys are a haven for water enthusiasts and outdoor adventurers. You can enjoy snorkeling, scuba diving, kayaking, paddleboarding, fishing, and boating in the pristine waters surrounding the islands. The abundant marine life and coral reefs make it an ideal destination for underwater exploration.

3. Unique Island Culture and Charm: Each island in the Florida Keys has its own distinct character and charm. From the lively and colorful streets of Key West to the relaxed and laid-back vibes of Islamorada and Marathon, you'll find a diverse mix of art, culture, music, and cuisine throughout the Keys.

4. Key West's Historic and Cultural Attractions: Key West, the southernmost city in the United States, is famous for its historic landmarks, lively nightlife, and artistic heritage. You can visit the Ernest Hemingway Home and Museum, explore the charming Old Town, witness the nightly Sunset Celebration at Mallory Square, and indulge in the vibrant dining and entertainment scene.

5. Island-Hopping and Road Trips: The Florida Keys are connected by the scenic Overseas Highway, allowing for memorable road trips and island-hopping adventures. You can explore the unique landscapes and communities of each island, from Key Largo in the north to Key West in the south, discovering hidden gems along the way.

When choosing a vacation rental in the Florida Keys, consider factors such as the specific island, proximity to attractions and activities, amenities offered, and the type of experience you desire. Whether you prefer a beachfront cottage, a waterfront villa, or a charming bungalow, the Florida Keys provide a captivating backdrop for a memorable vacation rental experience.

What cities are popular to rent a vacation rental in the Florida Keys?

When it comes to renting a vacation rental in the Florida Keys, there are several popular cities and islands that offer desirable options for visitors. Here are a few cities in the Florida Keys that are renowned for their vacation rental opportunities:

Islamorada: Located in the Upper Keys, Islamorada is often referred to as the "Sport Fishing Capital of the World." This picturesque island chain is famous for its world-class fishing, pristine beaches, and relaxed island vibes. In Islamorada, you can find vacation rentals that range from cozy waterfront cottages to spacious beachfront homes with private docks.

Key West: Key West is the southernmost city in the continental United States and a top destination for vacation rentals. Known for its vibrant nightlife, historic attractions, and lively atmosphere, Key West offers a wide range of vacation rental options, from charming cottages and historic homes in Old Town to waterfront condos and luxurious villas.

Marathon: Marathon is a centrally located island in the Florida Keys and offers a more tranquil and family-friendly atmosphere. It's known for its beautiful beaches, excellent fishing spots, and the stunning Seven Mile Bridge. Vacation rental options in Marathon include waterfront properties, canal-front homes, and condos with access to resort-style amenities.

Key Largo: As the northernmost and largest island in the Florida Keys, Key Largo provides a captivating blend of natural beauty and outdoor activities. It's known for its incredible diving and snorkeling opportunities, as well as its proximity to the Everglades. Key Largo offers vacation rentals that range from waterfront condos and villas to spacious homes with private pools.

These are just a few examples of popular cities and islands in the Florida Keys for vacation rentals. Other notable destinations include Big Pine Key, Tavernier, and Key Colony Beach, each offering their own unique charm and vacation rental options. Whether you're seeking a lively and bustling atmosphere or a more secluded and tranquil retreat, the Florida Keys have a variety of cities and islands to choose from to suit your preferences.

What do I need to know to rent a vacation home in the Florida Keys?

Renting a vacation home in the Florida Keys offers a wonderful opportunity to experience the beauty and charm of this unique destination. Here are some key things to know before renting a vacation home in the Florida Keys:

1. Research the Islands: The Florida Keys is a chain of islands, each with its own distinct character and offerings. Research the different islands, such as Key West, Islamorada, Marathon, Key Largo, and others, to determine which one aligns with your preferences in terms of atmosphere, activities, and amenities.

2. Booking in Advance: The Florida Keys are a popular vacation destination, especially during peak seasons. It's advisable to book your vacation rental well in advance to secure the best property that meets your needs. Consider booking several months ahead, especially if you have specific requirements or if you plan to visit during busy periods.

3. Rental Regulations and Licenses: Familiarize yourself with the vacation rental regulations and licensing requirements in the Florida Keys. Some islands may have specific rules and guidelines for vacation rentals, including occupancy limits, minimum rental periods, and permit requirements. Ensure that the property you choose complies with all applicable regulations.

4. Amenities and Features: Consider your desired amenities and features in a vacation rental. Do you prefer a beachfront property, a private pool, a dock for boating, or proximity to specific attractions? Determine your must-haves and use them as criteria when searching for vacation rentals.

5. Budget and Rates: Set a budget for your vacation rental and consider additional costs such as taxes, cleaning fees, and security deposits. Rates can vary depending on the island, location, property size, amenities, and the time of year you plan to visit. Be sure to factor in any additional expenses associated with your stay.

6. Read Reviews and Communication: Before finalizing your booking, read reviews and ratings from previous guests to gain insights into the property and the rental experience. Additionally, communicate directly with the property owner or rental agency to clarify any questions, discuss specific requirements, and ensure that the property meets your expectations.

7. Travel Insurance: Consider purchasing travel insurance to protect your investment in case of unforeseen circumstances or trip interruptions. Travel insurance can provide coverage for trip cancellations, delays, medical emergencies, and other unforeseen events.

By considering these factors and doing thorough research, you can find the perfect vacation home in the Florida Keys that aligns with your preferences, provides a comfortable stay, and allows you to fully enjoy the beauty and tranquility of this remarkable destination.

What popular islands to visit are found in the Florida Keys?

The Florida Keys offer a collection of popular and captivating islands to explore. Some of the well-known islands in the Florida Keys include:

1. Key West: The southernmost island is famous for its vibrant culture, historical sites, and lively nightlife. It's also a gateway to the beautiful Dry Tortugas National Park.

2. Islamorada: Often referred to as the "Sportfishing Capital of the World," Islamorada offers excellent fishing, water sports, and a laid-back atmosphere.

3. Key Largo: Known for its fantastic diving and snorkeling opportunities, Key Largo features the stunning John Pennekamp Coral Reef State Park.

4. Marathon: Positioned in the middle of the Keys, Marathon boasts picturesque beaches, water activities, and the popular Turtle Hospital.

5. Big Pine Key: This island is home to the Key Deer Refuge, where you can see the adorable and rare Key deer species.

6. Little Torch Key: Known for its tranquility, Little Torch Key offers a serene escape and beautiful sunsets.

7. Sugarloaf Key: A peaceful island with a relaxing atmosphere, perfect for those seeking a quiet retreat.

These are just a few examples of the diverse and captivating islands that make up the Florida Keys. Each island has its own unique charm, attractions, and opportunities for memorable experiences.

What is the Minimum Stay for a vacation rental in the Florida Keys?

Although there are a selection of licensed homes that may have been grandfathered in and available for shorter rentals here are the general minimum night stays in the Florida Keys;

  • Marathon has a minimum stay requirement of 7 days
  • Key Colony Beach has a minimum stay requirement of 7 days
  • Duck Key has a minimum stay requirement of 7 days
  • Key West requires a minimum stay of 28 days
  • Islamorada has a minimum stay requirement of 28 days
  • Key Largo has a minimum stay requirement of 28 days
  • Big Pine Key has a minimum stay requirement of 28 days
  • Little Torch Key has a minimum stay requirement of 28 days
  • Sugarloaf Key has a minimum stay requirement of 28 days
  • Summerland Key has a minimum stay requirement of 28 days
  • Ramrod Key has a minimum stay requirement of 28 days

What is the Typical Turnover Day for a Florida Keys rental?

Depending on the location of the rental by owner most hosts that rent for 7 days or weekly often have a Saturday turnover date during high season. Hosts that have to adhere to a 28 night minimum may choose to have different turnover days or start on the first of the calendar month. Although turnover days may vary by host.

  • Saturday for weekly stays
  • first calendar day of the month for min 28 night stays

Florida Keys Vacation Rental Price Information

Low range from $94 per night - $658 per week - $2,632 per month

High range from $2,006 per night - $14,042 per week - $56,168 per month

How early should I book a Florida Keys vacation rental?

Booking a Florida Keys vacation rental early is advisable, especially if you're planning to visit during the peak seasons or popular holidays. To secure your preferred property and dates, it's recommended to start looking and booking your vacation rental around 6 to 12 months ahead of your desired travel dates. This is particularly true if you have specific preferences for the type of property, location, or amenities you want.

Peak seasons in the Florida Keys, such as the winter months and holidays, tend to attract a high volume of visitors, and accommodations can fill up quickly. By booking well in advance, you'll have a wider selection of options and a better chance of securing the rental that meets your needs.

If you're planning to visit during the off-peak months, such as the warmer summer months, you might have more flexibility in terms of booking closer to your travel dates, as demand is generally lower during these times.

In either case, it's always a good idea to book your vacation rental as soon as you've finalized your travel plans to ensure you have the best choices available to you.

  • 6 to 12 months in advance to stay during high season

When is high season in the Florida Keys?

High season in the Florida Keys typically occurs during the winter months, from December to April. This period is characterized by pleasant weather, lower humidity, and a surge in tourism. The Florida Keys are particularly popular as a winter escape for travelers seeking warmth and outdoor activities during the colder months in other parts of the country.

Key factors that contribute to the high season include school holidays, snowbird migration, and the desire to enjoy the region's beaches, water sports, and cultural attractions in comfortable temperatures. It's important to note that within this high season, the peak months are often January, February, and March, when visitor numbers are at their highest.

Because of the increased demand during the high season, accommodations and activities tend to fill up quickly. To secure your preferred vacation rental and enjoy a smooth and memorable Florida Keys experience, it's recommended to book well in advance, especially if you're planning to visit during the peak months.

  • High season December to April

When is low season in the Florida Keys?

Low season in the Florida Keys typically occurs during the warmer and more humid months from May to November. This period is characterized by fewer tourists and a quieter atmosphere compared to the peak winter months. Low season is influenced by factors such as higher temperatures, increased chances of rainfall, and the avoidance of hurricane season.

While the low season might not be as popular as the high season due to the weather conditions, it does offer advantages such as more affordable accommodations, fewer crowds, and the opportunity to experience the Florida Keys in a more relaxed setting. Travelers who are looking for budget-friendly options and a more laid-back vacation experience may find the low season to be an ideal time to visit.

It's important to note that while the weather may be warmer and more humid, the Florida Keys still offer plenty of activities and attractions to enjoy, including water sports, fishing, wildlife viewing, and cultural experiences. Keep in mind that some businesses might have adjusted hours or limited operations during this time, so it's a good idea to plan accordingly.

  • Low season May to November

Are the Florida Keys a good spot to visit for a digital nomad or snowbird monthly stay?

Yes, the Florida Keys can be an excellent destination for both digital nomads and snowbirds looking for a monthly stay. Here's why:

Digital Nomads:

Scenic Workspaces: The stunning natural beauty of the Florida Keys provides an inspiring backdrop for remote work. Many accommodations offer ocean or waterfront views, creating a serene and motivating environment.

Reliable Connectivity: Most areas in the Florida Keys have reliable internet connectivity, essential for digital nomads to work effectively online.

Outdoor Activities: During breaks from work, you can enjoy outdoor activities like snorkeling, kayaking, and exploring the unique flora and fauna of the Keys.

Community: The Florida Keys have a warm and welcoming community. Engaging with locals and other digital nomads can provide opportunities for networking and socializing.


Winter Escape: The mild winter climate of the Florida Keys is a major draw for snowbirds looking to escape colder northern regions.

Monthly Rentals: Many vacation rentals in the Florida Keys offer monthly rates, allowing snowbirds to settle in comfortably for an extended stay.

Cultural Offerings: Snowbirds can enjoy the cultural attractions, events, and festivals that take place throughout the year in the Keys.

Leisure and Relaxation: The laid-back atmosphere and beautiful beaches make the Florida Keys a perfect place to relax and unwind during an extended stay.

Whether you're a digital nomad seeking a unique remote work experience or a snowbird looking for a warm and welcoming winter retreat, the Florida Keys offer a diverse range of options and activities to make your stay enjoyable and memorable.

There are currently Florida Keys monthly rentals on FLARBO

Sign In

Not registered yet?
Click here for traveler sign up
Click here for host sign up
Select your Account Type :
You will receive an email containing a link allowing you to reset your password to a new preferred one.


Already have an account?