Discover Your Perfect The Oldest House - Key West Vacation Homes

Best Vacation Homes in The Oldest House - Key West

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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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Why Choose Rent By Owner for your The Oldest House - Key West 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 The Oldest House - Key West Vacation Rentals

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

Staying in The Oldest House neighborhood of Key West offers a unique glimpse into the rich history and vibrant culture of this historic area. As you explore your surroundings, you'll find that this charming neighborhood is perfect for immersing yourself in the local atmosphere while enjoying the convenience of nearby attractions. Whether you’re seeking a peaceful retreat or an active adventure, booking a vacation rental here provides easy access to the best experiences in Key West. Discover the character and charm of this iconic location, making your stay both memorable and comfortable.

Key West Historic District

Located centrally in the region, the historic district offers a rich blend of cultural heritage and classic architecture, making it an ideal area to find charming vacation rentals close to local attractions.

View 2530+ Rentals in Key West Historic District

Old Town

This vibrant neighborhood provides a picturesque setting for your stay, with colorful streets and historic sites that make for a memorable experience in the region.

View 2470+ Rentals in Old Town

Sunset Key

For those seeking tranquility, Sunset Key offers secluded beaches and luxurious accommodations just a short ferry ride from here, perfect for unwinding in paradise.

View 3214+ Rentals in Sunset Key

Downtown

The bustling downtown area is filled with unique shops, lively eateries, and vibrant nightlife, making it a convenient choice for travelers looking to immerse themselves in the energy of the region.

View 1094+ Rentals in Downtown

Uptown - Upper Duval

Uptown's Upper Duval Street features a relaxed atmosphere with local cafes and art galleries, offering a laid-back environment for your stay within the city.

View 756+ Rentals in Uptown - Upper Duval

Bahama Village

Rich in Caribbean influence, this neighborhood provides a unique cultural experience with authentic cuisine and colorful architecture, ideal for exploring the diverse spirit of the destination.

View 97+ Rentals in Bahama Village

Historic Seaport

Situated along the waterfront, the historic seaport is perfect for those who want easy access to boating excursions and waterfront dining while staying within the heart of the area.

View 413+ Rentals in Historic Seaport

New Town

Offering a quieter alternative, New Town features residential-style vacation rentals and modern conveniences, ideal for a relaxing escape in the region.

View 118+ Rentals in New Town

Best Times to Visit The Oldest House - Key West

When should you plan your Vacation Rentals stay?

Timing your visit to this charming destination can enhance your experience, so consider planning during the shoulder seasons when the area offers pleasant weather and fewer crowds for a more relaxed getaway.

Peak Season Highlights

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Winter (December to February)

This is when you can enjoy the warm weather and lively atmosphere, making it ideal for exploring the area’s outdoor attractions and vibrant local events.

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

During spring, the region comes alive with blooming landscapes and pleasant temperatures, perfect for outdoor activities and cultural festivals.

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

Off-Season Highlights

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Summer (June to August)

While summer can be hot and humid, this period offers fewer crowds and more availability for those looking to enjoy a quieter stay in this destination.

Average Temperature Daytime: 88°F - Nighttime: 78°F
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Fall (September to November)

Autumn provides milder weather and lower rates, making it a good time to visit if you prefer a more relaxed experience without the peak season crowds.

Average Temperature Daytime: 85°F - Nighttime: 72°F

Weekly Weather Forecast for The Oldest House - Key West

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

More Top-Rated Vacation Rentals in The Oldest House - Key West 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 in the sunshine.
  • Take advantage of a shared or private swimming pool for refreshing dips after exploring the region.
  • Benefit from outdoor dining spaces perfect for alfresco meals in the warm climate.
  • Make use of outdoor grills for convenient barbecues with family and friends.
  • Relax on a spacious balcony or porch with views of the charming neighborhood.
  • Access lush landscaped gardens that add beauty and tranquility to your stay.
  • Utilize dedicated outdoor storage for bikes, surfboards, or other outdoor equipment.

Top Attractions Around The Oldest House - Key West

What attractions are nearby?

In this charming area, you can enjoy a variety of nearby activities such as exploring historic landmarks, strolling along scenic waterfronts, or indulging in local dining experiences, making your stay here truly memorable.

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Family Activities

  • Visit the Key West Shipwreck & Treasure Museum: Engage the family with interactive exhibits and learn about the region’s maritime history in this educational attraction.
  • Explore Fort Zachary Taylor Historic State Park: Enjoy a day of picnicking, swimming, and exploring one of the most historic landmarks on the island, perfect for outdoor family fun.
  • Discover the Mel Fisher Maritime Museum: Dive into fascinating stories of shipwrecks and treasure hunting, inspiring curiosity among children and adults alike.
  • Stroll through the Historic Seaport District: Take a leisurely walk along the waterfront, watching boats and enjoying family-friendly restaurants in this lively area.
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Adult Activities

  • Historical House Tour: Explore the oldest surviving structure in the area to immerse yourself in the region's rich history and architectural heritage.
  • Art Gallery Visits: Discover local artistry at renowned galleries within the historic district, offering a unique glimpse into the area's vibrant creative scene.
  • Sunset Pier Walks: Enjoy tranquil evenings strolling along the waterfront to witness breathtaking sunsets that highlight the region’s natural beauty.
  • Fine Dining Experiences: Savor exceptional seafood and regional cuisine at acclaimed restaurants nearby, perfect for appreciating the local flavor.

The Oldest House - Key West Travel Tips

How Can You Make the Most of Your Stay?

  • Embrace local culture: Take time to explore the area's historical sites and vibrant neighborhoods to truly experience the charm of this destination.
  • Plan outdoor activities early: Make the most of sunny days by scheduling your outdoor adventures during the cooler morning hours.
  • Discover nearby dining options: Sample local cuisine at popular eateries close to your vacation rental for authentic regional flavors.
  • Utilize the area’s transport options: Consider renting a bike or scooter to conveniently explore the historic streets and scenic spots around here.

Transportation Options

  • Walking: Exploring the area on foot allows you to enjoy the historic charm and vibrant streets of this destination, with many vacation rentals conveniently located within walking distance to local attractions.
  • Bike Rentals: Renting a bike offers an eco-friendly and flexible way to navigate here at your own pace, showcasing the scenic beauty of the region while reaching nearby points of interest easily.
  • Public Transportation: Utilizing local bus services provides a budget-friendly and convenient transportation option for discovering the region without the hassle of parking or driving.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services offer quick and reliable transportation, perfect for getting around here when visiting popular destinations or traveling late at night.

Local Customs Options

  • Respect for Historic Preservation: You should honor the area's commitment to maintaining its historic architecture and landmarks, which are integral to its unique charm.
  • Greeting with Warmth: It’s customary here to greet neighbors and visitors alike with a friendly smile and politeness, reflecting the region's welcoming spirit.
  • Celebrating Local Festivals: Participating in or observing local festivals and community events allows you to experience the rich cultural traditions unique to this destination.
  • Environmental Responsibility: You are encouraged to practice eco-friendly habits to preserve the natural beauty and vibrant marine life surrounding the area.

Frequently Asked Questions About The Oldest House - Key West?

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 3530 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 vacation rental in this historic area?

The cancellation policy varies depending on the specific property owner. You should review the listing details carefully or contact the host directly to understand the policy before finalizing your reservation.

4. How do I ensure my booking is secure and what payment options are available?

Bookings are processed through a secure platform that supports multiple payment methods. For peace of mind, verify the listing's security features and reach out to the host if you have any concerns about the payment process.

5. Are there any specific check-in and check-out times I should be aware of during my stay?

Check-in and check-out times are set by each host and detailed in the listing. It's recommended to communicate with the host beforehand to confirm your arrival time and ensure a smooth check-in process.

6. What amenities are typically included in these historical properties?

Amenities vary by listing but generally include essentials like Wi-Fi, kitchen facilities, and air conditioning. Review each property's amenities section thoroughly or contact the host for specific features tailored to your needs.

7. Is there a minimum stay requirement for booking here?

Minimum stay requirements depend on the individual property. Check the listing details or ask the host directly to confirm the length of stay required during your planned visit.

Best Vacation Homes in The Oldest House - Key West

10.0 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
View Availability