Vacation Rentals in Old Town Key West Florida

BOOK DIRECT

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

OLD TOWN 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 Old Town Key West

The Vacation Rental Properties listed below are professionally managed by Vacation Rental Management Companies who know the Old Town Key West area.

Vacation Rental Management Companies provide local hospitality, professional rental services, and the very best in rates and availability while managing vacation rentals that are safe for you and your family. They will assist you in finding the perfect rental property for your vacation.


Old Town Key West Florida Vacation Rentals

Private Spa Patio
$520/night
Townhouse in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

Tranquility
$350/night
Cottage in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Coconut Cabana
$600/night
Home in Old Town Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Campbell Eyebrow House
$225/night
Home in Old Town Key West Florida
1 Bed • 2 Full Baths • Sleeps 2
Historic Hideaways

Truman House
$1,170/night
Home in Old Town Key West Florida
4 Beds • 3 Full Baths • Sleeps 10
Historic Hideaways

Ann Street Gardens
$384/night
Cottage in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Hideaways

Coral Condo
$390/night
Condo in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Hideaways

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

Poinciana House
$553/night
Home in Old Town Key West Florida
1 Bed • 2 Full Baths • Sleeps 4
Historic Hideaways

Bella Vita
$325/night
Condo in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

Campbell Suite
$514/night
Condo in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

La Hacienda
$200/night
Home in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Duval Street Suite
$520/night
Townhouse in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Hideaways

La Isla Vita
$144/night
Home in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Havana Lane
$1,000/night
Cottage in Old Town Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

AnnStreetCottage
$325/night
Cottage in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Kemp House
$1,040/night
Home in Old Town Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Hideaways

Paradise Grand
$400/night
Home in Old Town Key West Florida
5 Beds • 4 Full Baths • Sleeps 10
Historic Hideaways

Noah's Retreat
$1,157/night
Home in Old Town Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Hideaways

Living Area
$117/night
Home in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways

The Courtyard
$384/night
Condo in Old Town Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Historic Hideaways


Nestled within the historic streets of Old Town Key West, Florida, vacation rentals offer a unique glimpse into the rich culture and vibrant atmosphere of this charming locale. From quaint cottages to luxurious estates, the range of accommodations caters to every traveler's taste and budget. But what truly sets these rentals apart is the seamless blend of modern comfort with old-world charm. As guests step foot into these carefully curated spaces, they are met with a sense of belonging and an invitation to become part of the fabric of this historic district.

Vacation Rental Options in Old Town Key West

When seeking vacation rental options in Old Town Key West, visitors can choose from a selection of 21 unique and inviting properties to ensure a memorable stay in this historic and charming area. Some of these rental options include waterfront properties that offer breathtaking views of the ocean, providing a serene and picturesque setting for guests to relax and unwind. Additionally, for those traveling with pets, there are pet-friendly accommodations available to cater to all members of the family. These properties are designed to meet the diverse needs of guests, whether they seek a tranquil retreat by the water or a place where their furry companions are welcome. With a range of options to choose from, visitors can find the perfect vacation rental for an unforgettable stay in Old Town Key West.

Unique House Rentals for Memorable Stays

To enhance the experience of visitors seeking unique accommodations in Old Town Key West, a selection of distinctive house rentals awaits, promising unforgettable stays in this historic and charming area. Whether you're looking for a cozy retreat by the beach or a luxurious waterfront villa, the options are diverse and cater to various preferences. Explore the following unique house rentals for a truly memorable vacation:

  • Charming beachfront cottages with stunning ocean views
  • Spacious waterfront villas offering a blend of luxury and relaxation
  • Historic houses with traditional Key West architecture and modern amenities
  • Quaint bungalows nestled in lush tropical gardens
  • Elegant mansions with private pools and panoramic sunset vistas

Experience the magic of Old Town Key West in these exceptional and carefully curated accommodations.

Booking Direct Benefits With Management Companies

Engage in a seamless and cost-effective vacation rental experience by directly booking with reputable management companies in Old Town Key West. By choosing to book directly, you can enjoy various advantages, including avoiding costly fees typically charged by third-party booking platforms. Connecting directly with a vacation rental management company also allows you to experience personalized services tailored to your specific needs and preferences. Moreover, management companies offer perks such as local hospitality and professional assistance throughout your stay, ensuring a smooth and enjoyable vacation experience. Take advantage of the benefits of direct booking with management companies in Old Town Key West to make the most of your vacation rental experience.

Key West Area Vacation Destinations

Discover the diverse and enticing vacation destinations within the Key West area, offering a range of professionally managed vacation rental properties to enhance your stay. Whether you seek beachfront accommodations or thrilling outdoor adventures, Key West has something for everyone. Here are some top vacation destinations in the area:

  • Key West: Explore the vibrant streets, charming architecture, and lively atmosphere of this iconic island city.
  • Old Town Key West: Immerse yourself in history and culture while staying in the heart of Key West's historic district.
  • Truman Annex of Key West: Experience luxury and exclusivity in this prestigious neighborhood near the waterfront.
  • Sunset Key: Indulge in a secluded island getaway with stunning views and upscale amenities.
  • Stock Island: Enjoy a more laid-back atmosphere with fishing, dining, and waterfront activities just a short drive from Key West.

Travel Guides and News for Old Town Key West

Curious about the latest travel guides and news for Old Town Key West? When exploring this vibrant area, immerse yourself in the local cuisine known for its fresh seafood and Caribbean influences. Discover hidden gems off the beaten path, such as quaint cafes serving Key Lime pie, or boutique shops offering unique souvenirs. Stay updated on events, festivals, and must-visit attractions through travel guides that highlight the rich history and culture of Old Town Key West. Uncover the best-kept secrets of the area, from picturesque alleyways to historic landmarks. Whether you're a food enthusiast, history buff, or nature lover, Old Town Key West has something to offer every type of traveler seeking an authentic experience.

Local Hospitality Services in Key West

Amidst the vibrant backdrop of Key West's tropical charm, a myriad of local hospitality services awaits to cater to the diverse needs of visitors seeking a seamless and enriching experience. Key West offers an array of local experiences and concierge services to ensure visitors make the most of their stay:

  • Walking Tours: Explore the rich history and hidden gems of Key West with knowledgeable local guides.
  • Boat Charters: Set sail on crystal-clear waters for a day of adventure, diving, or sunset cruises.
  • Bike Rentals: Pedal through picturesque streets and discover quaint cafes and boutiques at your own pace.
  • Food Tours: Indulge in local cuisine through guided culinary tours showcasing Key West's gastronomic delights.
  • Event Planning: Let local experts organize special occasions, ensuring memorable experiences in this tropical paradise.

Fun Things to Do in Old Town Key West

Exploring Old Town Key West unveils a tapestry of vibrant attractions and activities that capture the essence of this historic district's charm and character. Indulge in the local cuisine, from fresh seafood shacks to cozy cafes offering Key Lime pie, a local favorite. For those seeking adventure on the water, snorkeling, sunset cruises, and paddleboarding are popular choices. Dive into the rich history of the area by visiting landmarks like the Ernest Hemingway Home and Museum, or wander through the picturesque streets lined with colorful Victorian homes. Don't miss out on the lively atmosphere of Mallory Square, where street performers entertain crowds as the sun sets over the Gulf of Mexico. Old Town Key West promises a memorable experience for all visitors.

Professional Vacation Rental Management Services

Professional vacation rental management services play a crucial role in ensuring a seamless and enjoyable experience for guests seeking accommodations in Old Town Key West, Florida. These services are designed to provide top-notch support and assistance to both guests and property owners. Here are some key aspects managed by vacation rental management companies:

  • Property Maintenance: Regular upkeep and maintenance of the property to ensure it meets high standards.
  • Guest Communication: Effective communication before, during, and after the stay to address any queries or concerns promptly.
  • Marketing and Listing Management: Promoting the property to attract more guests and managing online listings.
  • Cleaning Services: Arranging professional cleaning services between guest stays.
  • 24/7 **Guest Support:** Providing round-the-clock assistance for any emergencies or issues that may arise during the stay.

Frequently Asked Questions

What Are Some Popular Local Restaurants and Dining Options Near Vacation Rentals in Old Town Key West?

When seeking local cuisine and waterfront dining near vacation rentals in Old Town Key West, visitors can indulge in an array of popular dining options. Experience the vibrant flavors of the region at renowned restaurants offering fresh seafood and Caribbean-inspired dishes. These dining establishments boast picturesque waterfront locations, providing a delightful ambiance to accompany the delectable culinary offerings. Immerse yourself in the culinary delights of Old Town Key West, where every dining experience is a memorable journey.

Are There Any Special Events or Festivals That Take Place in Old Town Key West Throughout the Year?

Key West hosts a variety of festivals and events throughout the year, drawing in visitors from all over. From the world-renowned Fantasy Fest celebrating all things creative and colorful, to the Key West Food and Wine Festival showcasing culinary delights, there is always something happening in this vibrant island city. Other notable events include the Key West Songwriters Festival and the Key West Lobsterfest, offering unique experiences that cater to diverse interests.

What Are Some Recommended Outdoor Activities or Excursions That Guests Can Participate in While Staying in Old Town Key West?

For guests staying in Old Town Key West, a variety of outdoor activities and excursions await. From snorkeling excursions exploring the vibrant underwater world, to bike tours uncovering the charming streets, there is something for every adventurer. Witness breathtaking sunsets on sunset cruises or feel the thrill of jet ski rentals along the coast. These activities offer a mix of relaxation and adventure, providing a truly unforgettable experience in Old Town Key West.

Are There Any Historical Landmarks or Museums in Old Town Key West That Guests Can Visit During Their Stay?

Guests staying in Old Town Key West can explore various historical landmarks and local museums during their visit. Key attractions include the Ernest Hemingway Home and Museum, showcasing the iconic writer's former residence and polydactyl cats. The Key West Lighthouse and Keeper's Quarters Museum offers panoramic views and insights into maritime history. Additionally, guests can visit the Mel Fisher Maritime Museum to learn about shipwrecks and underwater treasures.

What Transportation Options Are Available for Getting Around Old Town Key West, and Are There Any Recommended Modes of Transportation for Guests Staying in Vacation Rentals?

In Old Town Key West, various transportation options cater to visitors. Public transportation, including the City of Key West's bus system, provides convenient and affordable ways to explore the area. For a more leisurely and scenic experience, bike rentals are a popular choice, offering guests the flexibility to navigate the charming streets and discover hidden gems at their own pace. These modes of transportation enhance the vacation experience for guests staying in vacation rentals.


IDEA DRIVEN VACATIONS

Where to stay around Old Town Key West Florida

Our April 2024 property listings offer a selection of 21 vacation rentals near Old Town 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 Old Town Key West for a holiday or a weekend are on Find Rentals.


Where are the best places to stay in Old Town 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 Old Town Key West:

  • South Gulf Coast: 1,870 vacation rentals
  • Emerald Coast and Destin Area: 2,044 vacation rentals
  • Florida Keys: 507 vacation rentals

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


What are some fun things to do in Old Town Key West?

Find Rentals offers a selection of vacation rentals near parks and other areas of interest in Old Town Key West. Some of the most popular places to visit while you're traveling in Old Town Key West while on vacation are The Key West Butterfly and Nature Conservatory, Danger Charters, Nelson English Park, Fort Zachary Taylor Historic State Park, Blue Sky Charter Company LLC. and a few more.

There are many other points of interest around Old Town 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 Old Town Key West Florida?

  • Florida Keys Vacation Rentals: 283 vacation rental properties
  • Rent Key West Vacations: 58 vacation rental properties
  • Historic Hideaways: 34 vacation rental properties

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


How can I find a vacation rental manager in Old Town 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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