Discover Your Perfect Old Town Vacation Homes

Old Town Pet Friendly Vacation Rentals

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Old Town Large Vacation Homes

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6.8 (11 Reviews)
House
Tradewinds
  • Pet Friendly
  • View
  • Balcony/Terrace
View Availability
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Why Choose Rent By Owner for your Old Town 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 Old Town Vacation Rentals

Where are the best neighborhoods to stay in Old Town?

When exploring Old Town in Key West, Florida, you’ll find a variety of neighborhoods that perfectly suit different travel styles. Each area offers its own unique charm and easy access to the vibrant local culture, colorful architecture, and historic landmarks. Whether you prefer strolling through lively streets filled with boutique shops or relaxing in quiet, picturesque surroundings, choosing the right neighborhood can enhance your stay. With a wide selection of trustworthy vacation rentals, you'll discover comfortable and conveniently located options that make experiencing the best of Key West effortless and enjoyable.

Key West Historic District

In this area, you can enjoy charming streets filled with historic architecture and vibrant local culture, making it an ideal spot for exploring authentic Key West experiences.

View 2386+ Rentals in Key West Historic District

Downtown

Here, you'll find a lively atmosphere with easy access to shops, dining, and entertainment, offering a convenient base for discovering the region's top attractions.

View 1006+ Rentals in Downtown

Uptown - Upper Duval

This neighborhood offers a relaxed vibe with unique local spots, perfect for those seeking a quieter area while remaining close to the lively heart of the destination.

View 727+ Rentals in Uptown - Upper Duval

Bahama Village

Known for its colorful culture and welcoming community, staying in Bahama Village immerses you in a vibrant neighborhood rich in Caribbean influence.

View 93+ Rentals in Bahama Village

Historic Seaport

Staying near the harbor provides picturesque views and convenient access to waterfront activities, ideal for enjoying the area's maritime heritage.

View 382+ Rentals in Historic Seaport

Truman Annex

This exclusive enclave boasts historic charm and proximity to key sites, offering a peaceful retreat within the lively island environment.

View 330+ Rentals in Truman Annex

Midtown

Midtown presents a more residential setting with local eateries and parks, suited for travelers wanting an authentic experience away from tourists.

View 55+ Rentals in Midtown

Meadows

Set in a tranquil part of the region, Meadows provides a serene atmosphere while still being close to the area's popular attractions.

View 99+ Rentals in Meadows

Best Times to Visit Old Town

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, whether you're seeking lively festivals or peaceful beaches in this charming destination.

Peak Season Highlights

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Winter (December to February)

During the winter months, you can experience warm, pleasant weather perfect for exploring this tropical destination without the overwhelming heat.

Average Temperature Daytime: 75°F to 78°F - Nighttime: 65°F to 70°F
spring
Spring (March to May)

Springtime offers ideal conditions with lively atmosphere and plenty of sunshine, making it a popular period for visitors seeking vibrant local events and outdoor activities.

Average Temperature Daytime: 78°F to 82°F - Nighttime: 70°F to 74°F

Off-Season Highlights

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Summer (June to August)

In the summer, expect hotter and wetter weather, which can be a great time to find more affordable and less crowded vacation rentals here.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
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Fall (September to November)

Early fall features fewer tourists and cooler temperatures, providing a relaxed atmosphere for exploring this destination at your own pace.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 72°F to 76°F

Weekly Weather Forecast for Old Town

How to Book Your Old Town 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 Old Town

More Top-Rated Vacation Rentals in Old Town 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 unwind in the warm Floridian sun.
  • Take advantage of outdoor grilling areas for delicious meals in a scenic setting.
  • Relax by a sparkling shared or private pool, perfect for cooling off after exploring the area.
  • Make use of lush, landscaped gardens or courtyards that enhance your outdoor experience.
  • Stay active with access to tennis courts or other sports facilities on-site.
  • Benefit from convenient outdoor parking options close to your rental home.
  • Relish the tropical vibes with outdoor seating areas designed for social gatherings or quiet mornings.

Top Attractions Around Old Town

What attractions are nearby?

While staying here, you'll have the opportunity to explore a variety of nearby activities in the area, from vibrant dining and unique shopping experiences to scenic waterfront walks and cultural attractions that showcase the charm of this destination.

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Family Activities

  • Visit the Key West Aquarium: Discover marine life through interactive exhibits that are perfect for engaging children and adults alike in this family-friendly attraction.
  • Explore Mallory Square Sunset Celebration: Enjoy captivating street performers and a breathtaking sunset view, creating memorable moments for your family in this vibrant part of town.
  • Tour the Historic Lighthouse and Keeper's Quarters: Climb to the top for panoramic views and learn about the area's maritime history in this iconic landmark.
  • Relax at Fort Zachary Taylor Beach: Spend a fun-filled day swimming and picnicking at one of the region’s most scenic beaches, ideal for families seeking a relaxed outdoor experience.
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Adult Activities

  • Sipping cocktails on historic Duval Street: You can enjoy lively nightlife and unique local bars in the heart of Old Town, offering a true taste of the area's vibrant culture.
  • Exploring the Ernest Hemingway Home and Museum: Visiting this famous author’s residence gives you insight into the region's literary history and charming architecture.
  • Taking a sunset cruise from the nearby harbor: Experience breathtaking views of the coastline and the setting sun while relaxing aboard a boat in this seaside destination.
  • Strolling through the colorful streets of Old Town: Discover boutique shops, art galleries, and historic landmarks that showcase the region’s distinctive charm and character.

Other Places to Stay in Old Town, FL

Key West Wildlife Center
Key West Wildlife Center Vacation Rentals
Studios of Key West
Studios of Key West Vacation Rentals
Key West Burlesque Theater
Key West Burlesque Theater Vacation Rentals
Higgs Beach
Higgs Beach Vacation Rentals
Key West Garden Club
Key West Garden Club Vacation Rentals
Key West
Key West Vacation Rentals
Key West Historic District
Key West Historic District Vacation Rentals
Duval Street
Duval Street Vacation Rentals
Downtown
Downtown Vacation Rentals
Uptown - Upper Duval
Uptown - Upper Duval Vacation Rentals
Truman Annex
Truman Annex Vacation Rentals
Bahama Village
Bahama Village Vacation Rentals
More Places to Stay Near Old Town

Old Town Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Savor the authentic flavors by dining at local eateries to get a true taste of this destination's vibrant culinary scene.
  • Stroll Through Historic Districts: Take leisurely walks around the area’s historic streets to discover charming architecture and hidden gems unique to here.
  • Plan Water-Based Activities: Make the most of your stay by engaging in water sports or harbor cruises offered nearby, highlighting the region’s stunning coastline.
  • Visit Notable Landmarks: Allocate time to explore prominent sites that capture the essence of this destination’s rich history and culture.

Transportation Options

  • Walking: Exploring on foot allows you to fully immerse yourself in the charming streets and vibrant atmosphere of this destination's historic district.
  • Bicycle Rentals: Biking offers an eco-friendly and convenient way to navigate through the area while enjoying the scenic waterfront views and local attractions.
  • Taxi Services: Taxi options provide quick and comfortable transportation, giving you easy access to popular sites within the region.
  • Rental Cars: Renting a car grants flexibility for exploring beyond the immediate vicinity, perfect for those seeking to discover more of this destination at their own pace.

Local Customs Options

  • Conch Republic Independence Day: Celebrated on April 23rd, this unique local custom honors the area's history with vibrant parades and festivities that you can experience during your stay.
  • Fresh Seafood Dining Etiquette: Emphasizing the region's maritime roots, dining here often involves enjoying freshly caught seafood in a relaxed, informal setting that embodies the island's laid-back vibe.
  • Sunset Celebrations at Mallory Square: Every evening, locals and visitors gather to watch the sunset while enjoying street performers and local artisans, creating a lively atmosphere that captures the area's spirit.
  • Respect for Marine Environment: Preserving the region’s natural beauty is essential, so you'll find that eco-friendly practices and respectful interactions with marine life are deeply ingrained in local customs.

Frequently Asked Questions About Old Town?

1. What are the top vacation rentals in Old Town?

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

2. How many vacation rentals have private pools in Old Town?

There are 597 vacation rentals with private pools near Old Town. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Old Town are best for families?

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

4. How many Rentbyowner vacation rentals are available in Old Town?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 3444 in the Old Town 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 Old Town. 

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

Cancellation policies vary depending on the property owner. To understand the specific terms, please review the listing details or contact the property owner directly before booking.

6. How do I find out about the amenities included in a vacation rental in this area?

Details about amenities are listed on each property page. For any additional questions, reaching out to the owner will ensure you have all the necessary information before confirming your reservation.

7. Are there any house rules I should be aware of when staying here?

House rules are typically provided in the property listing. For clarification on specific policies, such as pet restrictions or smoking, it’s best to contact the owner directly.

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

Check-in and check-out procedures are detailed in each listing. Contact the property owner if you need further assistance or have special requests regarding your arrival or departure.

9. How can I ensure my reservation is secure when booking a vacation rental in this region?

Booking through a reputable platform provides secure payment options and verified listings. Always verify the property details and communicate with the owner through official channels to ensure a safe and smooth reservation process.

Old Town Top Rated Vacation Rentals

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