Discover Your Perfect Key West Historic District Vacation Homes

Key West Historic District Luxury Rentals

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Why Choose Rent By Owner for your Key West Historic District Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Key West Historic District Vacation Rentals

Where are the best neighborhoods to stay in Key West Historic District?

Exploring the neighborhoods in the Key West Historic District offers you a unique opportunity to immerse yourself in the charm and rich heritage of this vibrant area. Whether you prefer staying close to lively streets filled with local history or seeking a tranquil retreat within historic surroundings, you'll find a variety of vacation rentals that perfectly match your preferences. This central location provides easy access to the district’s renowned architecture, colorful streets, and cultural landmarks, making it an ideal choice for a memorable getaway. With trustworthy and reliable vacation rentals available, your stay in the Key West Historic District promises both comfort and convenience, ensuring a seamless experience from start to finish.

Old Town

In the heart of the historic region, Old Town offers charming streets and preserved architecture that make your stay in Key West truly authentic. This area is perfect for travelers seeking a blend of history and vibrant local culture.

View 2348+ Rentals in Old Town

Downtown

Centering around lively streets and cultural attractions, Downtown provides convenient access to the best dining, shopping, and entertainment options here in the region. It’s an ideal choice for those wanting an energetic atmosphere right outside their vacation rentals.

View 1020+ Rentals in Downtown

Uptown - Upper Duval

Uptown – Upper Duval features quieter streets and scenic views, offering a relaxed setting for your stay in this destination. It’s suited for visitors looking for tranquility while still being close to key attractions.

View 723+ Rentals in Uptown - Upper Duval

Bahama Village

Rich in history and Caribbean influence, Bahama Village delivers a colorful experience just moments from your vacation rentals. Here, you can enjoy a lively neighborhood full of local charm and unique cultural flavor.

View 94+ Rentals in Bahama Village

Historic Seaport

Situated along the waterfront, the Historic Seaport offers picturesque views and easy access to boating activities near your vacation accommodations. It’s perfect for travelers eager to explore maritime history and indulge in waterside leisure.

View 395+ Rentals in Historic Seaport

Truman Annex

Known for its historic significance and charming ambiance, Truman Annex provides an exclusive retreat with stylish vacation rentals and close proximity to the area’s attractions. It’s ideal for those seeking privacy and elegance.

View 333+ Rentals in Truman Annex

The Meadows

This peaceful neighborhood offers lush greenery and a tranquil environment, making it a great choice for relaxation during your stay here. It’s well-suited for visitors looking for a quiet escape within the region.

View 99+ Rentals in The Meadows

White St. Gallery

Located near the artistic hub of the destination, White St. Gallery showcases local creativity, providing a culturally rich backdrop for your vacation rentals. It’s perfect for art lovers wanting to immerse themselves in the local scene.

View 29+ Rentals in White St. Gallery

Best Times to Visit Key West Historic District

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here depends on your preferences for weather, special events, and avoiding peak crowds, ensuring you make the most of your stay in this charming destination.

Peak Season Highlights

winter
Winter (December to April)

During the winter months, this destination experiences its peak tourist season, drawing visitors who seek warm weather and vibrant local events. Booking your vacation rentals early ensures you secure the best options in the area.

Average Temperature Daytime: 75°F - Nighttime: 65°F
spring
Spring Break (March to April)

Spring Break attracts a lively crowd to this region, making it an ideal time for enjoying the vibrant atmosphere and bustling activities. Securing your vacation rentals well in advance is recommended for this popular period.

Average Temperature Daytime: 78°F - Nighttime: 67°F

Off-Season Highlights

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Summer (June to August)

Summertime sees fewer visitors here, offering a more relaxed environment and often better availability for booking vacation rentals. Take advantage of this quieter season to explore at your own pace.

Average Temperature Daytime: 85°F - Nighttime: 77°F
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Fall (September to November)

During fall, the area experiences lower tourism levels, making it a great time to enjoy more affordable vacation rentals and less crowded attractions. It’s an excellent choice for a peaceful getaway.

Average Temperature Daytime: 82°F - Nighttime: 72°F

Weekly Weather Forecast for Key West Historic District

How to Book Your Key West Historic District Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Key West Historic District

More Top-Rated Vacation Rentals in Key West Historic District Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or garden area to relax after exploring the vibrant streets of the district.
  • Take advantage of communal swimming pools available at some properties, perfect for cooling off in the warm Floridian climate.
  • Utilize outdoor grilling stations to prepare fresh seafood and local delicacies in your own backyard setting.
  • Benefit from bike storage or rental options, making it easy to explore the charming surroundings on two wheels.
  • Relax on sun loungers or hammocks set up in outdoor living spaces, ideal for soaking up the sunny weather here.
  • Access lush courtyards or landscaped gardens that highlight the tropical ambiance of this historic region.
  • Make use of outdoor dining areas to enjoy meals with friends or family while taking in the lively atmosphere nearby.

Top Attractions Around Key West Historic District

What attractions are nearby?

In this vibrant region, you can explore a variety of nearby activities including historic tours, waterfront dining, and lively art galleries, all conveniently accessible from your choice of vacation rentals in the area.

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Family Activities

  • Key West Historic District Trolley Tour: Embark on a family-friendly trolley tour to explore the area's rich history and colorful architecture at your own pace.
  • Visit the Ernest Hemingway Home and Museum: Discover the legendary author's residence, where kids can learn about literary history and see the famous six-toed cats.
  • Explore Mallory Square Sunset Celebration: Enjoy an evening of street performers, local artisans, and breathtaking sunsets that captivate visitors of all ages.
  • Discover the Key West Shipwreck Treasure Museum: Engage your family with interactive exhibits that reveal the region's shipwrecking history and maritime adventures.
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Adult Activities

  • Sunset Celebration at Mallory Square: Experience the vibrant evening festivities with street performers and breathtaking sunsets right in the heart of the historic district.
  • Historic Seaport Tours: Embark on a boat tour from the vicinity to explore the region's maritime history and enjoy scenic views of the coastline.
  • Duval Street Nightlife: Immerse yourself in the lively nightlife with eclectic bars, live music venues, and charming cafés along this iconic street.
  • Key West Lighthouse and Keeper's Quarters Museum: Discover local history by visiting this historic landmark, offering panoramic views and insightful exhibits about the area's maritime past.

Other Places to Stay in Key West Historic District, FL

Studios of Key West
Studios of Key West Vacation Rentals
Key West Burlesque Theater
Key West Burlesque Theater Vacation Rentals
Key West Firehouse Museum
Key West Firehouse Museum Vacation Rentals
Key West Cemetery
Key West Cemetery Vacation Rentals
Saint Mary Star of the Sea
Saint Mary Star of the Sea Vacation Rentals
The Kite House
The Kite House Vacation Rentals
Key West
Key West Vacation Rentals
Old Town
Old Town Vacation Rentals
Duval Street
Duval Street Vacation Rentals
Downtown
Downtown Vacation Rentals
Uptown - Upper Duval
Uptown - Upper Duval Vacation Rentals
Historic Seaport
Historic Seaport Vacation Rentals
More Places to Stay Near Key West Historic District

Key West Historic District Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Historic District on Foot: Walking through the area allows you to fully appreciate its charming architecture and hidden courtyards at your own pace.
  • Visit Local Shops and Eateries: Take advantage of nearby boutiques and waterfront restaurants to immerse yourself in the local culture and flavors.
  • Plan Your Activities Wisely: Schedule visits to popular sites early in the morning or later in the evening to avoid crowds and enjoy a more relaxed experience.
  • Choose a Central Vacation Rental: Booking a property within the district ensures easy access to the area's best attractions and vibrant nightlife, enhancing your stay here.

Transportation Options

  • Walking: Exploring on foot allows you to immerse yourself in the charming streets and historic sites of the area, making it ideal for discovering nearby vacation rentals.
  • Biking: Renting a bike offers a convenient and eco-friendly way to navigate through the region’s scenic routes and vibrant neighborhoods.
  • Public Transportation: The local trolley and bus services provide affordable and accessible options for reaching various attractions from your vacation rental here.
  • Taxi and Rideshare Services: Convenient for quick trips or traveling longer distances within this destination, ensuring you arrive comfortably at your rental and explore the region effortlessly.

Local Customs Options

  • Conch Republic Independence Day: Celebrated every April, this local custom honors the area's unique history with festive parades and patriotic displays that you can experience firsthand during your stay.
  • Lower Keys Customs of Fishing and Boating: Embraced as a way of life here, fishing and boating are integral to the region’s culture, offering many opportunities for you to enjoy these traditional activities.
  • Respect for Eco-Friendly Practices: Sustainability is highly valued, with residents and visitors alike participating in eco-conscious efforts to preserve the natural beauty of this destination.
  • Historic Preservation Traditions: Maintaining the historic charm of the area is a community priority, so you'll notice a strong emphasis on preserving architecture and cultural landmarks during your visit.

Frequently Asked Questions About Key West Historic District?

1. What are the top vacation rentals in Key West Historic District?

There are a lot of options in Key West Historic District. If you plan on staying in the Key West Historic District area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Key West Historic District:

2. How many vacation rentals have private pools in Key West Historic District?

There are 610 vacation rentals with private pools near Key West Historic District. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Key West Historic District are best for families?

If you are looking for a family-friendly vacation home in Key West Historic District, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Key West Historic District:

4. How many Rentbyowner vacation rentals are available in Key West Historic District?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 3576 in the Key West Historic District area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Key West Historic District. 

5. What is the cancellation policy for bookings in this historic district?

Cancellation policies vary depending on the individual property listing. You should review the specific policy on the rental's page or contact the property owner directly for detailed information regarding cancellations and any applicable fees.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning charges, service taxes, or security deposits are often listed on the property details page. It's recommended to read the full listing description carefully or reach out to the owner to clarify any extra costs before completing your reservation.

7. Is it possible to customize my stay or request special amenities at these rentals?

Many hosts are willing to accommodate special requests or provide personalized amenities. To ensure your needs can be met, contact the property owner directly before booking to discuss any specific requirements you may have.

8. What is the check-in and check-out process for vacation rentals in this area?

Check-in and check-out procedures are usually outlined in the property listing. For a smooth experience, communicate with the host beforehand to confirm arrival times and any necessary access instructions.

9. How do I ensure my reservation is secure and reliable?

Booking through a reputable platform that offers verified listings and secure payment options helps ensure your reservation is trustworthy. Always review the property's reviews and contact the owner if you have any concerns before confirming your stay.

Key West Historic District Top Rated Vacation Rentals

See More Key West Historic District Vacation Rentals