Discover Your Perfect Downtown Vacation Homes

Downtown Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Downtown 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 Downtown Vacation Rentals

Where are the best neighborhoods to stay in Downtown?

Staying in Downtown Key West puts you at the heart of this vibrant Florida neighborhood, where charming streets and lively establishments create an inviting atmosphere. Whether you're seeking a serene retreat or a dynamic nightlife scene, this area offers a diverse selection of vacation rentals that cater to your preferences. By choosing a property here, you'll enjoy easy access to the local culture and waterfront views, making your stay in this iconic destination both convenient and memorable. Experience the authentic essence of Key West by booking your ideal accommodation in the downtown area, where comfort and accessibility go hand in hand.

Key West Historic District

Staying in the Key West Historic District places you at the heart of the area's vibrant history and culture, offering easy access to charming architecture and local landmarks. This neighborhood provides an authentic experience for those seeking to explore the region's rich heritage through comfortable vacation rentals.

View 2909+ Rentals in Key West Historic District

Old Town

In Old Town, you'll find a lively atmosphere with colorful streets and historic sites, making it ideal for discovering the essence of the area. Here, well-appointed vacation rentals allow you to immerse yourself fully in the unique charm of this popular destination.

View 2827+ Rentals in Old Town

Uptown - Upper Duval

Opting for Uptown - Upper Duval means enjoying a lively neighborhood scene with a variety of dining and entertainment options close by. The area offers convenient vacation rental choices perfect for exploring everything this vibrant part of the city has to offer.

View 874+ Rentals in Uptown - Upper Duval

Bahama Village

Located in the region, Bahama Village is known for its colorful character and cultural richness, providing a cozy setting for your stay. Vacation rentals here give you the chance to experience the area's local flavor and welcoming community.

View 107+ Rentals in Bahama Village

Historic Seaport

The Historic Seaport is perfect for travelers wanting scenic waterfront views and maritime charm, with vacation rentals that place you close to boat tours and seaside activities. It’s an ideal choice for enjoying the region’s nautical atmosphere.

View 461+ Rentals in Historic Seaport

Truman Annex

Choosing Truman Annex means staying in a peaceful yet accessible neighborhood, featuring luxurious vacation rentals near scenic parks and historic sites. It’s a prime spot for experiencing the regional blend of tranquility and adventure.

View 379+ Rentals in Truman Annex

Best Times to Visit Downtown

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this vibrant area ensures you can fully enjoy the unique atmosphere and local charm of your vacation here, making it essential to consider seasonal trends and regional climate when planning your stay.

Peak Season Highlights

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Winter (December to April)

During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and sunny skies. Expect lively atmospheres and higher demand for vacation rentals in the area.

Average Temperature Daytime: 75°F - 80°F - Nighttime: 65°F - 70°F
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Summer (June to August)

The summer months bring the highest influx of travelers eager to enjoy the region's vibrant atmosphere and outdoor activities. Vacation rentals tend to book quickly during this bustling season.

Average Temperature Daytime: 85°F - 90°F - Nighttime: 75°F - 80°F

Off-Season Highlights

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Spring (April to June)

In spring, the area sees a slight dip in visitor numbers, offering more availability and relaxed ambiance for those looking to explore at a slower pace. It's an ideal time for affordable vacation rentals.

Average Temperature Daytime: 78°F - 85°F - Nighttime: 68°F - 75°F
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Fall (September to November)

Autumn offers a quieter experience with fewer crowds, making it perfect for discovering the region’s charms without the peak-season rush. Vacation rentals are often more accessible and budget-friendly.

Average Temperature Daytime: 80°F - 85°F - Nighttime: 70°F - 75°F

Weekly Weather Forecast for Downtown

How to Book Your Downtown 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 Downtown

More Top-Rated Vacation Rentals in Downtown 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 balcony to relax and soak up the sunny Florida weather.
  • Take advantage of lush garden spaces or landscaped courtyards that add to the tropical ambiance.
  • Make use of the swimming pool, often available in downtown accommodations for a refreshing escape.
  • Utilize outdoor dining areas perfect for al fresco meals in the warm climate.
  • Benefit from barbecue grills or outdoor kitchens to host gatherings under the sun or stars.
  • Relax on loungers or sun decks designed for soaking up the region’s vibrant sunshine.
  • Access nearby waterfront views or dock areas if your rental is close to the coast or harbor.

Top Attractions Around Downtown

What attractions are nearby?

Within this vibrant area, you can enjoy a variety of activities such as exploring historic sites, indulging in local cuisine, and taking scenic boat tours, all conveniently accessible from your downtown Key West vacation rentals.

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Family Activities

  • Beachfront Family Fun: Spend a day at the sandy shores of this coastal area, where you can enjoy swimming, building sandcastles, and relaxing by the water.
  • Historic Lighthouse Tour: Explore the iconic lighthouse, offering educational insights and stunning views that captivate visitors of all ages.
  • Conch Republic Marine Park: Discover underwater adventures with family-friendly snorkeling and paddleboarding experiences in the vibrant marine park nearby.
  • Old Town Key West Walking Tour: Take a guided stroll through the historic district, immersing your family in the colorful architecture and local stories that make this destination unique.
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Adult Activities

  • Sunset Sails: Embark on a scenic cruise to enjoy breathtaking sunsets over the Gulf of Mexico, a perfect way to unwind in this vibrant area.
  • Duval Street Nightlife: Experience the lively atmosphere and diverse entertainment options along Duval Street, a hub for adult nightlife and local culture.
  • Historic Seaport District: Explore the charming waterfront with its unique shops, dining establishments, and opportunities for boat tours that showcase the area's maritime history.
  • Conch Tour Train: Take a guided ride through the region’s historic streets and neighborhoods to discover the rich stories and architecture that define this destination.

Other Places to Stay in Downtown, FL

Key West
Key West Vacation Rentals
Tennessee Williams Key West Exhibit
Tennessee Williams Key West Exhibit Vacation Rentals
Reworx
Reworx Vacation Rentals
Ernest Hemingway Home and Museum
Ernest Hemingway Home and Museum Vacation Rentals
San Carlos Institute - Casa Cuba
San Carlos Institute - Casa Cuba Vacation Rentals
Jackson Square
Jackson Square Vacation Rentals
Duval Street
Duval Street Vacation Rentals
More Places to Stay Near Downtown

Downtown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining: Immerse yourself in the area's vibrant culinary scene by trying out popular local eateries and fresh seafood spots near your vacation rental.
  • Visit Historic Sites: Take time to discover the region’s rich history by visiting well-known landmarks and museums that capture the essence of this destination.
  • Enjoy Waterfront Activities: Make the most of the nearby waters by engaging in activities like boating, fishing, or simply relaxing along scenic waterfronts.
  • Experience Nightlife and Events: Dive into the lively atmosphere here by attending evening events or exploring bars and live music venues in the heart of downtown.

Transportation Options

  • Walking: Exploring the area on foot allows you to comfortably access many local attractions, shops, and restaurants from your vacation rental in Downtown, Key West.
  • Bicycle Rentals: You can rent a bike to enjoy an eco-friendly and flexible way to discover the vibrant streets and scenic waterfronts of this destination.
  • Scooter or Moped Rentals: Opt for a scooter or moped to easily navigate through busy streets and reach popular spots around the region with minimal effort.
  • Taxi and Rideshare Services: Conveniently get around in the area using reliable taxi or rideshare options that connect you directly to your preferred destinations within downtown Key West.

Local Customs Options

  • Conch Shell Blowing: Engaging in the local tradition of blowing conch shells is a respected custom here, often heard during celebrations and special events, adding to the island’s vibrant atmosphere.
  • Reef Preservation Etiquette: Respect for marine life is vital when visiting this destination, with locals practicing sustainable snorkeling and diving habits to preserve the region's stunning coral reefs.
  • Celebration of Pirates' Heritage: Participating in or observing pirate-themed festivities reflects the area's historical roots and lively culture that you can experience during your stay.
  • Supporting Local Artisans: Buying handcrafted goods from market stalls exemplifies the community’s appreciation for its artistic traditions and offers authentic souvenirs to remember your visit.

Frequently Asked Questions About Downtown?

1. What are the top vacation rentals in Downtown?

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

2. How many vacation rentals have private pools in Downtown?

There are 178 vacation rentals with private pools near Downtown. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Downtown are best for families?

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

4. How many Rentbyowner vacation rentals are available in Downtown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1380 in the Downtown 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 Downtown. 

5. What is the cancellation policy for vacation rentals in Downtown, Key West?

Cancellation policies vary depending on the specific listing you choose. It’s essential to review the individual rental's cancellation terms before booking or contact the property owner directly for detailed information.

6. Are there any specific check-in and check-out times I should know about for rentals in this area?

Check-in and check-out times are typically specified in each listing. To ensure a smooth arrival and departure, review these details carefully or reach out to the host for clarification.

7. How do I find the most suitable vacation rental in the region for my needs?

Use filters such as dates, amenities, and price range to narrow down your choices. You can also read property descriptions and reviews or contact hosts directly to confirm if the rental meets your requirements.

8. Is there a secure method to pay for my booking in this destination?

Payments are processed through secure channels provided by the booking platform. For added peace of mind, verify the payment options listed in your chosen rental's details and contact support if needed.

9. What should I do if I encounter an issue during my stay at a vacation rental here?

In case of problems, contact the property owner immediately using the contact information provided. If further assistance is needed, reach out to customer support through the platform for prompt resolution.

Downtown Top Rated Vacation Rentals

See More Downtown Vacation Rentals