Discover Your Perfect Key West Vacation Homes

Why Choose Rent By Owner for your 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.

Best Times to Visit Key West

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this charming destination can enhance your experience, as the best seasons for enjoying the area’s pleasant climate and local events typically fall during specific months of the year.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities and exploring this destination at your own pace.

Average Temperature Daytime: 85°F - Nighttime: 70°F
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Fall (September to November)

Early fall offers pleasant temperatures and fewer crowds, providing a peaceful environment to fully enjoy the region's natural beauty and local events.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Off-Season Highlights

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Winter (December to February)

During this period, temperatures are cooler, and the area tends to be less busy, offering a more relaxed stay for those seeking tranquility and lower rates.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Spring (March to May)

Springtime welcomes milder weather and blossoming scenery, but shoulder season travelers can often take advantage of better deals and fewer visitors here.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Weekly Weather Forecast for Key West

How to Book Your 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 Key West

More Top-Rated Vacation Rentals in 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 deck for relaxing and dining al fresco amidst the region’s scenic views.
  • Take advantage of an outdoor swimming pool to cool off during warm summer days in this welcoming destination.
  • Benefit from a well-equipped grilling area perfect for hosting cookouts with friends and family.
  • Explore the surrounding nature with access to nearby hiking trails, ideal for outdoor enthusiasts visiting here.
  • Make use of spacious yards or gardens to enjoy outdoor games and activities with your loved ones.
  • Secure convenient parking spaces within the property for easy transportation around the area.
  • Relax in an inviting outdoor lounge area designed for socializing and unwinding in the fresh air.

Top Attractions Around Key West

What attractions are nearby?

While staying here, you can explore a variety of outdoor activities and local attractions that showcase the charm of this destination in Iowa, ensuring your visit is both enjoyable and memorable.

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Family Activities

  • Key West, Iowa, USA Family Farm Tour: Discover the charming family farm experiences where you can learn about local agriculture and enjoy interactive activities suitable for all ages.
  • Historic District Exploration: Take a walk through the area’s historic sites, offering educational insights and family-friendly sightseeing opportunities that highlight the region's proud heritage.
  • Local Nature Trails: Explore scenic routes perfect for hiking or biking, providing a great way for your family to connect with the natural beauty surrounding this destination.
  • Community Events and Festivals: Participate in seasonal festivals and community gatherings that foster memorable family fun and allow you to mingle with locals in Iowa’s welcoming atmosphere.
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Adult Activities

  • Exploring the local art scene: You can enjoy discovering vibrant galleries and art installations that showcase the region's creative spirit, all easily accessible from your vacation rental.
  • Fishing at the regional lakes: Spend a relaxing day casting lines in nearby lakes renowned for their abundant fish populations, perfect for unwinding here.
  • Hiking through scenic trails: Experience the natural beauty of this destination by taking hikes along well-maintained trails that wind through picturesque landscapes close to your lodging.
  • Sampling regional cuisine: Delight in experiencing authentic local flavors at popular eateries and cafes, conveniently located within the area for your convenience.

Key West Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Discover the area’s hidden gems and popular spots to enrich your stay in this charming destination.
  • Plan Water Activities: Take advantage of the region’s waterways by engaging in boating, fishing, or kayaking for an authentic experience.
  • Visit Seasonal Events: Check out local events and festivals happening during your visit to immerse yourself in the community’s culture.
  • Book Early for Popular Properties: Secure your preferred vacation rentals early to ensure a seamless and stress-free getaway experience here.

Transportation Options

  • Car Rentals: Exploring the area is most convenient with car rentals, giving you flexibility to visit nearby attractions and enjoy your stay comfortably.
  • Public Transit: Public transportation options provide an affordable and eco-friendly way to navigate here without needing a personal vehicle.
  • Taxis and Rideshare Services: Taxis and rideshare apps offer quick, reliable transportation for getting around without the hassle of parking or driving yourself.
  • Biking and Walking: This destination's scenic routes are perfect for biking or walking, allowing you to explore at your own pace while soaking in the local atmosphere.

Local Customs Options

  • Local Seafood Cuisine: You’ll find that enjoying fresh, locally caught seafood is a cherished tradition among residents here, often featured in community gatherings and local eateries.
  • Community Festivals: Participating in seasonal festivals and parades gives you a taste of the region’s vibrant community spirit and rich cultural heritage.
  • Respect for Nature: It’s customary to practice environmental mindfulness, especially when exploring outdoor areas or water activities in this destination.
  • Traditional Music and Dance: Embracing local musical styles and dance forms at community events offers an authentic way to connect with the area’s cultural roots.

Frequently Asked Questions About Key West?

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. Which vacation homes in Key West are best for families?

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

3. 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 26 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. 

4. What is the cancellation policy for vacation rentals in Key West, Iowa?

Cancellation policies vary depending on the property listing. You should review the specific terms outlined on the listing page or contact the property owner directly to understand the cancellation and refund procedures for your stay.

5. How do I inquire about amenities and house rules before booking?

Details about available amenities and house rules are typically provided within the listing description. If you have further questions, reaching out directly to the property owner can ensure you get all the necessary information before confirming your reservation.

6. Are there any restrictions on the length of stay at vacation rentals in this area?

Stay duration requirements can differ by property. Some listings may require minimum night stays, especially during peak seasons. It's best to check the specific listing details or ask the owner for clarification.

7. What measures are in place for guest safety and cleanliness?

Safety and cleanliness standards are maintained according to local regulations and property-specific practices. For detailed information about cleaning protocols and safety measures, contact the owner or review the listing details.

8. How do I handle payment and deposits when booking a vacation rental here?

Payment methods and deposit requirements are specified in each listing. Typically, a secure online payment system is used, and deposits may be required to confirm your reservation. Details will be provided during the booking process or upon contacting the owner.

Key West Top Rated Vacation Rentals

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