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Discover Your Perfect Key West Rentals by Owner

Key West Rentals by Owner

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10.0 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
View Availability
More Top-Rated Rentals by Owner in Key West Area

Why Choose Rent By Owner for your 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 Key West Rentals by Owner

Where are the best neighborhoods to stay in Key West?

When planning your stay in Key West, Florida, choosing the right neighborhood can greatly enhance your vacation experience. From the lively streets near Duval Street to the more relaxed atmospheres of Old Town, each area offers its own unique charm and proximity to local attractions. Whether you prefer the vibrant energy of downtown or a tranquil retreat by the water, finding the perfect rental by owner through Rent By Owner ensures a seamless booking process. Discover the ideal neighborhood that suits your style and enjoy an authentic Key West adventure tailored just for you.

Key West Historic District

Stay in the heart of the region's most historic area, where charming architecture and vibrant cultural heritage create an authentic Floridian experience. Here, you’re perfectly positioned to explore the storied past and lively atmosphere that define this iconic part of town.

View 2856+ Rentals in Key West Historic District

Old Town

This neighborhood offers a blend of classic charm and modern appeal, making it an ideal choice for those seeking a walkable area filled with local character. Here, convenient access to popular attractions and waterfront views enhances your stay in this scenic destination.

View 2765+ Rentals in Old Town

Sunset Key

Relax on this tranquil island just off the coast, where upscale resorts and pristine beaches promise a peaceful retreat. Visitors favor its exclusivity and stunning sunsets, making it a perfect escape within the region.

View 3214+ Rentals in Sunset Key

Downtown

The bustling hub of activity, downtown offers an energetic vibe with diverse dining, shopping, and entertainment options. Staying here puts you close to the lively core of the city’s nightlife and cultural scene.

View 1213+ Rentals in Downtown

Uptown - Upper Duval

Located in a vibrant part of town, this neighborhood features a mix of local shops and casual eateries, ideal for experiencing authentic regional life. It's a great base for exploring the area's artistic and cultural offerings.

View 865+ Rentals in Uptown - Upper Duval

Bahama Village

Rich in Caribbean-inspired culture, this neighborhood offers colorful streets and lively festivals, providing a distinctive flavor to your stay. It’s perfect for travelers looking to immerse themselves in local traditions and unique community events.

View 105+ Rentals in Bahama Village

Historic Seaport

Set along the waterfront, this area offers scenic harbor views and maritime activities, making it an excellent choice for those interested in a nautical ambiance. The proximity to boat tours and seaside eateries enhances your experience here.

View 464+ Rentals in Historic Seaport

New Town

This growing neighborhood combines residential comfort with convenient access to key transportation routes, ideal for travelers who prefer a quieter, more relaxed environment while remaining connected to the region’s attractions.

View 123+ Rentals in New Town

Best Times to Visit Key West

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, as the best seasons often align with pleasant weather and fewer crowds, making it ideal for booking your rental by owner through Rent By Owner in this popular destination.

Peak Season Highlights

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February to April

During these months, you'll experience the most vibrant atmosphere in this destination, with pleasant weather ideal for exploring and enjoying outdoor activities.

Average Temperature Daytime: 75-82°F - Nighttime: 65-70°F
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December to January

This period offers a lively holiday season with warm winter temperatures, making it perfect for comfortable sightseeing and relaxing by the water.

Average Temperature Daytime: 72-78°F - Nighttime: 62-67°F

Off-Season Highlights

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May to August

As the region transitions into summer, you may find fewer crowds and more availability, while enjoying hot weather that’s great for water activities.

Average Temperature Daytime: 85-89°F - Nighttime: 77-81°F
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September to November

Autumn brings cooler temperatures and less tourist traffic, offering a peaceful escape for those seeking tranquility and lower prices.

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

Weekly Weather Forecast for Key West

How to Book Your 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 Key West

More Top-Rated Rentals by Owner in 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 after a day of exploring the region.
  • Take advantage of a shared or private pool to cool off in the warm Florida sun.
  • Benefit from lush, tropical landscaping that enhances your outdoor experience during your stay.
  • Make use of barbecue grills for convenient outdoor dining with friends and family.
  • Relax on furnished patios or balconies that provide picturesque views of the area's scenery.
  • Access outdoor showers to rinse off after a day at nearby beaches or water activities.
  • Utilize outdoor storage spaces to keep your beach gear and water sports equipment organized and accessible.

Top Attractions Around Key West

What attractions are nearby?

Nearby, you can explore a variety of activities such as relaxing on scenic beaches, engaging in vibrant water sports, or discovering local culture at nearby historic sites—all conveniently accessible from your rental by owner in this popular vacation destination.

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Family Activities

  • Key West Aquarium: Explore marine life through interactive exhibits and engaging displays suitable for families seeking educational fun in the area.
  • Fort Zachary Taylor Historic State Park: Enjoy a day of sun, sand, and swimming at this scenic park offering picnic areas and historic fort tours, perfect for family outings.
  • Conch Tour Train: Take a guided train tour around the region that provides entertaining insights into the area's history and highlights, ideal for family sightseeing adventures.
  • Smathers Beach: Relax and play on one of the most popular beaches here, with calm waters and plenty of space for building sandcastles and family fun in the sun.
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Adult Activities

  • Sunset Sail Cruises: Experience breathtaking views of the sunset while relaxing on a classic sailboat along the coast, immersing yourself in the beauty of this coastal destination.
  • Historic Old Town Tours: Explore the charming streets and architecture that tell the story of the area's rich history, offering a unique perspective of your vacation locale.
  • Scuba Diving and Snorkeling Adventures: Discover vibrant marine life and coral reefs just off the shores, providing an unforgettable underwater experience here in the region.
  • Fishing Excursions: Try your hand at deep-sea or flats fishing, a popular activity that allows you to enjoy the area's abundant aquatic resources.

Other Places to Stay in Key West, FL

Key West Historic District
Explore 2,856 Properties
Old Town
Explore 2,765 Properties
Duval Street
Explore 2,078 Properties
Downtown
Explore 1,213 Properties
Uptown - Upper Duval
Explore 865 Properties
Historic Seaport
Explore 464 Properties
Truman Annex
Explore 373 Properties
Midtown
Explore 364 Properties
New Town
Explore 123 Properties
The Meadows
Explore 117 Properties
Meadows
Explore 117 Properties
Bahama Village
Explore 105 Properties
More Places to Stay Near Key West

Key West Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Take advantage of the region's popular attractions by booking tours and experiences in advance through your rental host to ensure a smooth trip.
  • Explore Local Cuisine: Savor authentic flavors at nearby eateries and consider staying close to dining hotspots for convenient access to the area's culinary delights.
  • Use Water Transportation: Make the most of the area’s waterways by utilizing boats or ferries, which often provide unique perspectives of the region’s scenic coastline and islands.
  • Respect the Environment: Embrace eco-friendly practices during your stay, such as conserving water and disposing of waste responsibly, to help preserve this beautiful destination for future visitors.

Transportation Options

  • Rental Car Services: Explore the region at your own pace with convenient rental car options available here, offering flexibility to visit all the scenic spots and local attractions.
  • Public Transportation (Bus System): Utilize the reliable bus network that serves the area, providing an affordable and eco-friendly way to navigate through this popular destination.
  • Bicycle Rentals: Enjoy the picturesque surroundings on two wheels with bicycle rentals, a healthy and environmentally conscious way to experience the region’s charm.
  • Taxis and Rideshare Services: Get around easily with professional taxi operators and rideshare options that connect you quickly to key locations within the area.

Local Customs Options

  • Respect for Local Art and History: You’ll find that supporting local artists and heritage is a cherished custom here, so consider engaging with art galleries or historical sites during your stay.
  • Relaxed Dress Code: Casual, comfortable clothing is customary when exploring the region’s laid-back lifestyle, especially in outdoor dining and beach areas.
  • Celebration of Nautical Traditions: Embrace the area's maritime culture by participating in or observing local events that honor the region’s deep-seated connection to the sea.
  • Environmental Awareness: The community values eco-friendly practices, so practicing sustainable tourism helps preserve this destination’s natural beauty and charm.

Frequently Asked Questions About Key West Rentals by Owner

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

There are a lot of options in Key West. If you plan on staying in the 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 Key West:

2. How many Rentbyowner vacation rentals are available in Key West?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 3235 in the 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 Key West. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary depending on the individual listing. You should review the specific cancellation terms listed for each property or contact the owner directly to understand the options available.

4. How do I communicate with the property owner before booking?

You can reach out to the owner through the messaging feature on the booking platform. This allows you to ask questions about the rental, clarify details, and ensure it meets your needs.

5. Are there any additional fees beyond the nightly rate I should be aware of?

Additional fees such as cleaning charges, service fees, or local taxes are often listed in the property details. It's best to review these fees carefully or contact the owner for clarification before confirming your reservation.

6. What amenities are typically included in rentals by owner here?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, linens, and air conditioning. For specific amenities, consult the listing details or contact the owner directly.

7. Is there a minimum stay requirement when booking a rental by owner in this region?

Minimum stay requirements depend on the individual property and season. Check the listing details or contact the owner to confirm the minimum stay applicable for your desired dates.

More Rentals You May Like Near Key West

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10.0 (2 Reviews)
House
Duval Hideaway
  • Parking
  • Pet Friendly
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Key West Area