Vacation Rentals in Key West Florida

KEY WEST

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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

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

Pool & Jacuzzi Area Vista Fresco at 1800 Atlantic Key West
$230/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Quilted Giraffe
$650/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Paradise Grand
$300/night
Home in Key West Florida
5 Beds • 4 Full Baths • Sleeps 10
Historic Hideaways

Island Time
$130/night
Condo in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Hideaways

Reynold's Retreat Key West Private Pool
$232/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Private Parking at Villa de Palmas Key West
$199/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Banana Key
$364/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Escape on Fleming Key West Monthly Rental
$110/night
Apartment in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Rent Key West Vacations

Casa de Cuba Key West
$850/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

La Brisa Key West #303 W Dining Area
$128/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

The Courtyard
$260/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

livingroom-todoor
$777/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 8
Rent Key West Vacations

Poolside Palms
$293/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

pp_1
$190/night
Studio in Key West Florida
• 1 Full Bath • Sleeps 2
Rent Key West Vacations

Private Pool Southernmost Kentucky Home Key West
$284/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Townhomes on Windsor #3
$750/night
Townhouse in Key West Florida
3 Beds • 3 Full Baths • Sleeps 1
Rent Key West Vacations

La Isla Vita
$130/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

DSC_10-0485
$225/night
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 6
Rent Key West Vacations

Balcony View Casa Atlantica One Bedroom Key West
$246/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Paradise Place #5 @ Duval Square Key West Entryway Looking In
$286/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Stairs to Second Level Courtyard Condo @ Duval Square Key West
$486/night
Condo in Key West Florida
3 Beds • 2 Full Baths • Sleeps 8
Rent Key West Vacations

Royal Palm
$312/night
Townhouse in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Colony Key West Conch Casa Front Porch
$187/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
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.





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