Discover Your Perfect The Oldest House - Key West Rentals by Owner

The Oldest House - Key West Rentals by Owner

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10.0 (4 Reviews)
House
Mar Y Sol Ocean Front
  • Parking
  • Accessibility
  • Security/Safety
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10.0 (3 Reviews)
House
Somewhere on the beach
  • Pool
  • Accessibility
  • Security/Safety
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10.0 (3 Reviews)
Apartment
The Perch on Duval
  • Security/Safety
  • Child Friendly
  • Internet
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10.0 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
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More Top-Rated Rentals by Owner in The Oldest House - Key West Area

Why Choose Rent By Owner for your The Oldest House - Key West vacation rental?

What makes our Rentals by Owner 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 The Oldest House - Key West Rentals by Owner

Where are the best neighborhoods to stay in The Oldest House - Key West?

When choosing a neighborhood to stay in The Oldest House - Key West, you’ll find yourself immersed in a charming and historic part of Key West, Florida. This area offers a unique blend of rich history and vibrant local culture, making it an ideal spot for travelers seeking an authentic experience. As you explore the neighborhood, you’ll enjoy easy access to beautiful streets and quaint surroundings that capture the essence of Key West. Booking a rental by owner here ensures a trustworthy and seamless stay in one of the most picturesque parts of the city, perfect for discovering all that this iconic destination has to offer.

Key West Historic District

Within the historic district, you can immerse yourself in the area's rich cultural heritage while enjoying convenient access to local attractions. Staying here offers a perfect blend of history and proximity, making it an ideal choice for those seeking authentic experiences.

View 2949+ Rentals in Key West Historic District

Old Town

This vibrant neighborhood provides charming streets and a lively atmosphere, putting you close to Key West’s renowned sites. Choose here to enjoy the authentic vibe of the region while having easy access to nearby amenities and entertainment.

View 2864+ Rentals in Old Town

Sunset Key

For a tranquil retreat, Sunset Key offers serene surroundings with stunning views, just a short boat ride from the main area. It’s an excellent spot for those seeking relaxation while still being within reach of the region’s attractions.

View 3214+ Rentals in Sunset Key

Downtown

The downtown area is perfect if you want to stay in the heart of the action, with easy access to shopping, dining, and nightlife. Here, you’ll be at the center of the region’s lively scene, ideal for exploring everything here has to offer.

View 1282+ Rentals in Downtown

Uptown - Upper Duval

Uptown offers a more relaxed ambiance while still being close to the bustling Duval Street. It’s a great choice for visitors wanting a quieter stay without sacrificing convenience or access to local hotspots.

View 890+ Rentals in Uptown - Upper Duval

Bahama Village

Known for its colorful culture and friendly atmosphere, Bahama Village invites you to experience a unique side of this destination. Staying here means enjoying a vibrant community while remaining near the region’s key attractions.

View 107+ Rentals in Bahama Village

Historic Seaport

Situated along the waterfront, the historic seaport provides scenic views and easy access to boating activities. It’s an ideal location for those interested in experiencing the region’s maritime heritage.

View 463+ Rentals in Historic Seaport

New Town

Offering a more residential feel, New Town combines comfort with convenience, making it suitable for travelers seeking a peaceful stay close to local services and transportation options.

View 126+ Rentals in New Town

Best Times to Visit The Oldest House - Key West

When should you plan your Rentals by Owner stay?

Choosing the ideal time to visit ensures you can enjoy the charm and comfort of your rental here in this destination’s unique climate, helping you make the most of your experience in this historic area.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak season with warm, inviting weather that attracts visitors seeking a tropical escape. Booking early ensures you secure a comfortable rental by owner in this popular period.

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

Springtime marks another high travel period when many travelers flock here to enjoy pleasant temperatures and vibrant local events. It’s an ideal time to find a rental by owner for a memorable stay in the region.

Average Temperature Daytime: 80°F - Nighttime: 70°F

Off-Season Highlights

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Summer (June to August)

While summer is considered off-peak, it offers quieter surroundings with lower accommodation prices. You can still enjoy warm weather and less crowded attractions when booking your rental by owner now.

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

The fall months tend to see fewer visitors, making it a peaceful time to explore while securing a rental by owner at favorable rates. The weather remains warm, perfect for relaxing here during the shoulder season.

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

Weekly Weather Forecast for The Oldest House - Key West

How to Book Your The Oldest House - Key West vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 The Oldest House - Key West

More Top-Rated Rentals by Owner in The Oldest House - Key West Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 private outdoor seating areas perfect for relaxing or dining al fresco.
  • Take advantage of lush gardens or landscaped yards that enhance the outdoor ambiance.
  • Make the most of a refreshing private swimming pool to cool off under the warm Florida sun.
  • Utilize an outdoor grill or barbecue for preparing delicious meals in the open air.
  • Benefit from shaded patios or verandas offering comfortable spaces to unwind after exploring the area.
  • Discover convenient parking options within the property's outdoor space to simplify your stay.
  • Experience the charm of a private balcony or terrace that provides picturesque views of the surroundings.

Top Attractions Around The Oldest House - Key West

What attractions are nearby?

Immerse yourself in the vibrant local culture with a variety of nearby activities to enjoy, from exploring historic sites to relaxing on scenic beaches just moments from this prime location in Key West.

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Family Activities

  • Visit the Key West Shipwreck Museum: Dive into the area's maritime history and explore interactive exhibits that captivate the whole family.
  • Relax at Fort Zachary Taylor Beach: Enjoy a day of sun and sand at this popular beach, perfect for picnics and swimming just a short drive from here.
  • Explore the Mel Fisher Maritime Museum: Discover fascinating artifacts from shipwrecks that highlight the region's rich seafaring heritage.
  • Take a Conch Tour Train Ride: Experience an engaging and informative tour around the area, ideal for families eager to learn about local culture and history.
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Adult Activities

  • Historical Tours: Immerse yourself in the area's rich history by taking guided walking tours that highlight its unique past and cultural heritage.
  • Architectural Exploration: Discover the region's distinctive architecture by visiting historic homes and landmarks, offering a glimpse into the area's storied past.
  • Art and Cultural Events: Attend local art exhibits and cultural festivals to experience the vibrant community spirit here and engage with regional talent.
  • Relaxing Waterfront Activities: Enjoy leisurely strolls along the waterfront or indulge in sunset cruises that showcase the scenic beauty of this destination.

The Oldest House - Key West Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area's renowned seafood and Caribbean-inspired dishes by visiting local eateries to enrich your cultural experience.
  • Plan Your Transportation: Consider renting a bike or scooter to easily navigate the historic streets and uncover hidden gems around this charming destination.
  • Discover Unique Attractions: Make time to visit nearby landmarks and museums that highlight the rich history of the region, adding depth to your stay.
  • Engage with the Community: Attend local events or markets to connect with residents and gain authentic insights into the area's vibrant culture.

Transportation Options

  • Walking: You can comfortably explore the historic district on foot, immersing yourself in the area's charming streets and local sights.
  • Bicycle Rentals: Renting a bicycle is an eco-friendly way to navigate this destination, offering flexibility and a closer connection to the surrounding scenery.
  • Taxi Services: Taxis provide convenient door-to-door transportation around here, ideal for quick trips or when carrying luggage.
  • Public Transportation: Local buses serve the region efficiently, allowing you to easily access key attractions without hassle.

Local Customs Options

  • Respect for Historic Preservation: You will find that maintaining the charm of this destination involves honoring its historic architecture and local landmarks, which are cherished by residents and visitors alike.
  • Emphasis on Relaxed Social Norms: The area embraces a laid-back attitude, encouraging you to enjoy the easygoing vibe while engaging with friendly locals who value a casual and welcoming environment.
  • Environmental Awareness: Respect for the natural surroundings is key here, with many local customs promoting eco-friendly practices and conservation efforts during your stay.
  • Celebration of Local Art and Culture: Participating in community events and supporting local artisans is a common custom that enriches your experience of this region’s vibrant cultural scene.

Frequently Asked Questions About The Oldest House - Key West Rentals by Owner

1. What are the top vacation rentals in The Oldest House - Key West?

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

2. How many Rentbyowner vacation rentals are available in The Oldest House - Key West?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 2464 in the The Oldest House - Key West 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 The Oldest House - Key West. 

3. What is the cancellation policy for booking a rental by owner in this historic district?

The cancellation policy varies depending on the specific owner’s terms listed on the property page. It is recommended that you review these details carefully before confirming your reservation, or contact the owner directly for clarification.

4. How do I confirm the availability of a rental by owner during my travel dates?

Availability is updated regularly on the listing. You can check real-time availability by entering your desired dates, but for further confirmation or special requests, reaching out to the owner through the platform will ensure accurate information.

5. Are there any specific house rules or amenities I should know about before booking?

Each rental by owner has its own set of house rules and amenities, which are detailed in the listing description. Reading these thoroughly will help you prepare for your stay and ensure it meets your expectations.

6. What is the process for checking in and out at the property?

Check-in and check-out procedures are typically outlined in the listing details or communicated directly by the owner. Contact the owner prior to your arrival to coordinate key exchange or access instructions for a smooth experience.

7. Who should I contact if I encounter issues during my stay or have questions about the property?

For any concerns or questions during your visit, you should contact the property owner or the local support team provided through the booking platform. They are available to assist and ensure your stay is comfortable.

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