Vacation Rentals in Key West Florida

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Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

KEY WEST

BOOK DIRECT

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

KEY WEST AREA DESTINATIONS

Map of Key West

Why is Key West Florida such a Special Place?

Key West is a unique island and has its own atmosphere separate from any other place in the world. It is the southernmost city in the continental United States. The Old Town Architecture, Duvall Street Bars and Shops, Bahama Village, Fantasy Fest, Banyan Trees, Sunsets, Hemingway House, and Rodriguez Cigar Store are not to be missed. The geograhy of Key West make fishing, snorkeling, and kayaking in the mangroves a unique experience. The lively nightlife, beaches, historic sites, pirate history, iconic Key Lime Pie, pink shrimp, eclectic culture, vibe, and energy make Key West one of our favorite places to vacation.

The Vacation Rental Properties listed below are professionally managed by Vacation Rental Management Companies who know Key West Florida.


Key West Florida Vacation Rentals

Beach Club Seabreeze #103
$375/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Rent Key West Vacations

Covered Patio and Pool Tucked Away Key West
$250/night
Home in Key West Florida
2 Beds • 4 Full Baths • Sleeps 6
Rent Key West Vacations

Paradise Place #5 @ Duval Square Key West Entryway Looking In
$340/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Key West Beach Club 206 Private Balcony 3
$665/night
Condo in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Key West Beach Club Paradise Penthouse #401 Private Balcony
$400/night
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Matisse's Studio @ the Galleria Key West - Common Area Pool
$139/night
Studio in Key West Florida
• 1 Full Bath • Sleeps 2
Rent Key West Vacations

Tiki Beach Too Back Deck
$302/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Living Room Colony Calypso Key West
$219/night
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Townhomes On Windsor #4
$750/night
Townhouse in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Dining Area
$100/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

Open Concept Living and Dining CasaBella @ Duval Square Key West
$325/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Living room and dining area Artist's House @ Duval Square Key West
$300/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Balcony
$263/night
Condo in Key West Florida
• 1 Full Bath • Sleeps 2
Rent Key West Vacations

Balcony View
$300/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Living Area Key West's Crown Jewel
$400/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Pool & Jacuzzi Area Vista Fresco Key West
$390/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Private Pool
$200/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Shared Pool
$150/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Ashe Splashe
$180/night
Home in Key West Florida
2 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Front Porch
$181/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Living Room Colony Poolside Key West
$278/night
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Living Room Colony Sunset Suite Key West
$278/night
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 4
Rent Key West Vacations

Private Pool and Patio
$220/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Entrance
$400/night
Home in Key West Florida
4 Beds • 6 Full Baths • Sleeps 9
Rent Key West Vacations


As you consider your next escape to the sun-soaked paradise of Key West, Florida, the assortment of vacation rentals available beckons exploration. With a myriad of options nestled in this vibrant island city, each promising its own unique charm and proximity to the area's renowned attractions, the decision of where to stay becomes a tantalizing choice. From quaint cottages to luxurious beachfront villas, the offerings cater to every preference and budget, ensuring a memorable stay amidst the laid-back ambiance and captivating allure of Key West.

Key West Vacation Rental Overview

Key West's vacation rental scene offers a myriad of accommodation options to suit diverse preferences and needs, providing visitors with a personalized and comfortable stay in this vibrant island city. Rental amenities in Key West range from cozy cottages with private pools to luxurious condos overlooking the ocean, ensuring a delightful stay for every traveler. Moreover, guests can savor the flavors of local cuisine by exploring the numerous seafood restaurants, Cuban eateries, and charming cafes scattered throughout the area. Whether seeking a relaxing retreat or an adventure-filled vacation, Key West's vacation rentals cater to all, promising a memorable experience immersed in the island's rich culture and culinary delights.

Key West Area Highlights

Amidst Key West's vibrant vacation rental scene, the area's highlights beckon with a tapestry of unique attractions and experiences that encapsulate the essence of this southernmost city in the continental U.S. Key West offers a myriad of experiences that cater to diverse interests, including:

  • Beachfront resorts: Enjoy the luxury and convenience of staying right by the beautiful beaches of Key West.
  • Local cuisine: Delight your taste buds with the tantalizing flavors of Key West's local cuisine, from fresh seafood to authentic Cuban dishes.
  • Sunset celebrations: Witness breathtaking sunsets at Mallory Square, where locals and tourists gather for the lively sunset celebration each evening.

Key West Attractions and Features

Nestled within the vibrant tapestry of the southernmost city in the continental U.S., Key West's attractions and features offer a captivating blend of history, culture, and natural beauty. The island's allure is enriched by the legendary Hemingway House, where the iconic writer once lived, providing a glimpse into his life and works. Key West's pirate lore adds a touch of mystery and adventure, with tales of swashbuckling buccaneers and hidden treasures echoing through the streets. Beyond these historical gems, the island boasts a plethora of activities such as fishing and snorkeling, inviting visitors to immerse themselves in the abundant marine life and turquoise waters. Key West is a destination where every corner holds a story waiting to be discovered.

Key West Travel Guides

Enhancing your Key West adventure with comprehensive and detailed travel guides ensures a seamless and enriching experience on this unique island destination. Key West offers a plethora of resources to help you navigate the area and make the most of your stay. Here are some key elements to look out for in the travel guides:

  • Insider Tips: Discover hidden gems and off-the-beaten-path spots recommended by locals.
  • Local Cuisine: Delve into the vibrant food scene of Key West, from fresh seafood shacks to upscale dining options.
  • Upcoming Events: Stay informed about festivals, concerts, and cultural events happening during your visit.

Key West Accommodation Options

Key West offers a diverse selection of accommodation options, with 94 vacation rentals available including homes, condos, and cottages managed by three different vacation rental managers. These rental properties come with a variety of amenities to cater to different preferences, ranging from fully equipped kitchens and private pools to waterfront views and outdoor grilling areas. Booking options are flexible, allowing visitors to secure their desired accommodations through direct booking for cost savings and improved services. Whether you're looking for a cozy cottage in Old Town Key West or a luxurious condo in Truman Annex, Key West's accommodation options provide a comfortable and convenient stay for travelers seeking the perfect vacation rental experience.

Frequently Asked Questions

What Are Some Recommended Local Restaurants and Bars Near the Vacation Rentals in Key West?

When seeking local cuisine, happy hours, live music, or beachfront dining near vacation rentals in Key West, consider exploring the vibrant dining and entertainment scene. Key West boasts an array of restaurants and bars that cater to diverse tastes and preferences. From beachfront eateries offering fresh seafood to lively bars with live music, visitors can indulge in an authentic Key West experience while enjoying delicious meals and refreshing drinks.

Are There Any Restrictions or Guidelines for Renting Vacation Properties in Key West?

Key West vacation rental regulations play a crucial role in maintaining standards and ensuring a positive experience for both guests and property owners. These guidelines often cover aspects such as occupancy limits, noise restrictions, and rental permit requirements. Keeping abreast of Key West vacation rental trends is essential to stay competitive in the market and cater to evolving guest preferences. Adhering to regulations and staying informed about trends can help maximize the success of vacation rental properties.

What Is the Best Mode of Transportation for Getting Around Key West From the Vacation Rentals?

For navigating Key West from vacation rentals, the best modes of transportation are bike rentals and public transportation. Renting a bike allows for flexibility, easy parking, and a chance to explore the island at a leisurely pace. Public transportation, such as buses or trolleys, offers convenience and cost-effective options for reaching various attractions and destinations. Both options provide unique ways to experience the charm and beauty of Key West while getting around efficiently.

Are There Any Hidden Gems or Lesser-Known Attractions Near the Vacation Rentals in Key West?

Exploring Key West's lesser-known attractions reveals hidden gems such as secluded beaches perfect for a peaceful retreat. Local art galleries showcase the vibrant creativity of the area. Secret gardens offer tranquil escapes from the hustle and bustle. Offbeat attractions like quirky museums and historic sites provide unique experiences. Delve into these overlooked treasures near Key West vacation rentals to discover the island's diverse and eclectic charm.

How Can Guests Make the Most Out of Their Stay in Key West, Beyond the Typical Tourist Activities?

To make the most of their stay in Key West beyond typical tourist activities, guests can explore a plethora of outdoor adventures like kayaking through mangroves or paddleboarding along the crystal-clear waters. Delve into cultural experiences by visiting local artisans' studios, discovering unique handmade crafts, or partaking in eco-friendly activities such as snorkeling in coral reefs or visiting wildlife sanctuaries. Engage with the island's natural beauty and vibrant community for an unforgettable Key West experience.

Trending in Key West

Key West Songwriters Festival

Key West Songwriters Festival
by Anthony Vaarwerk

Key West Brewfest

Key West Brewfest
by Anthony Vaarwerk


IDEA DRIVEN VACATIONS

Where to stay around Key West Florida

Our March 2024 property listings offer a selection of 95 vacation rentals near Key West. Find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Key West for a holiday or a weekend are on Find Rentals.


Where are the best places to stay in Key West?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Key West:

  • South Gulf Coast: 1,824 vacation rentals
  • Emerald Coast and Destin Area: 2,092 vacation rentals
  • Florida Keys: 509 vacation rentals

For nearby neighborhoods, please use our search to access the selection of vacation rentals available in and around Key West.


What are some fun things to do in Key West?

Find Rentals offers a selection of vacation rentals near parks and other areas of interest in Key West. Some of the most popular places to visit while you're traveling in Key West while on vacation are The Key West Butterfly and Nature Conservatory, Higgs Beach Dog Park, Indigenous Park, Blue Sky Charter Company LLC., Fran Ford White-crowned Pigeon Preserve and a few more.

There are many other points of interest around Key West listed on Find Rentals where you can find a great place to stay. Try out the search to find a large selection of vacation rentals available near the city or region you're traveling to.


Which vacation rental managers have properties for rent in Key West Florida?

  • Florida Keys Vacation Rentals: 286 vacation rental properties
  • Rent Key West Vacations: 58 vacation rental properties
  • Historic Hideaways: 33 vacation rental properties

Can I rent homes in Key West?

Yes. Find Rentals has 42 homes available for rent in Key West. Our other popular types of vacation rentals in Key West include:

  • Condos : 29 rentals available
  • Cottages : 14 rentals available
  • Townhouses : 6 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including apartments and more.


Can I rent fishing rentals in Key West?

Absolutely, Find Rentals has 79 fishing rentals in Key West. You have also many other possibilities in Key West area, including:

Please use our search bar to access the selection of vacation rentals.


How can I find a vacation rental manager in Key West?

Find Rentals is the premiere guide for Vacation Rental Managers. We work with management companies from all over the world to provide you with the most robust selection of professionally managed rentals. Use the search to access the selection of management companies and rentals available.





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