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  3. Key West
  4. The Meadows
  5. Rentals by Owner

Discover Your Perfect The Meadows Rentals by Owner

The Meadows Rentals by Owner

More Top-Rated Rentals by Owner in The Meadows Area

Why Choose Rent By Owner for your The Meadows 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 The Meadows Rentals by Owner

Where are the best neighborhoods to stay in The Meadows?

Choosing the right neighborhood in The Meadows, Key West, Florida, can greatly enhance your vacation experience. This peaceful and inviting area offers convenient access to local attractions while providing a tranquil atmosphere for relaxation. Whether you're seeking a quiet retreat or a vibrant community feel, staying in The Meadows allows you to enjoy the authentic charm of Key West. When booking through Rent By Owner, you’ll find a variety of rental options from trusted owners that suit your needs perfectly, ensuring a seamless and dependable stay in this desirable part of the island.

Key West Historic District

Living in this area places you at the heart of Key West's vibrant history, offering easy access to iconic architecture and cultural landmarks while enjoying the welcoming atmosphere. It's an ideal choice for travelers seeking authentic experiences with convenient locations for exploring the region.

View 2527+ Rentals in Key West Historic District

Old Town

Staying here means immersing yourself in the charming streets filled with colorful homes and lively local shops, perfect for those wanting to experience the true essence of the destination. This neighborhood provides a central hub that combines history, art, and relaxed island living.

View 2462+ Rentals in Old Town

Midtown

The region offers a quieter, more residential setting while still being close to key attractions, making it suitable for visitors looking for a peaceful retreat near the area's vibrant core. It’s an excellent base for exploring the diverse sights and sounds of the destination.

View 52+ Rentals in Midtown

Meadows

Here, you’ll find a serene environment that balances comfort and convenience, ideal for those wanting a relaxing stay within easy reach of Key West’s popular sites. This neighborhood provides a peaceful backdrop for your vacation with accessible amenities.

View 97+ Rentals in Meadows

White Street Gallery District

This lively district offers an eclectic mix of art, shops, and cafes, creating a dynamic setting for your stay. It provides a fantastic opportunity to explore local culture while enjoying comfortable rental options in the area.

View 24+ Rentals in White Street Gallery District

Best Times to Visit The Meadows

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider visiting during the region's shoulder seasons when the weather is pleasant and rental rates are often more favorable, ensuring a comfortable and cost-effective vacation here in The Meadows, Key West.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and sunshine. You can enjoy pleasant daytime temperatures and vibrant local activities.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
spring
Spring (March to May)

Springtime draws travelers looking for ideal weather before the summer rush. The region offers comfortable temperatures perfect for outdoor exploration and relaxing stays.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 68°F to 72°F

Off-Season Highlights

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Summer (June to August)

While summer is warmer, it’s considered off-peak, making it an excellent time for budget-conscious travelers. Expect higher humidity but fewer crowds during your stay here.

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

Fall sees a slight dip in visitor numbers, offering a quieter experience for those who prefer less crowded accommodations while enjoying mild weather.

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

Weekly Weather Forecast for The Meadows

How to Book Your The Meadows 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 The Meadows

More Top-Rated Rentals by Owner in The Meadows 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 swimming pools to relax and unwind in the sunshine.
  • Take advantage of lush landscaped gardens perfect for strolling or outdoor yoga sessions.
  • Use outdoor grilling stations to prepare delicious meals while enjoying the warm climate.
  • Benefit from spacious patios or decks ideal for outdoor dining and entertaining guests.
  • Make the most of shaded areas with pergolas or gazebos for relaxing in the fresh air.
  • Access outdoor lounge furniture designed for lounging and soaking up the sunshine.
  • Explore nearby walking or biking paths that showcase the natural beauty of the region.

Top Attractions Around The Meadows

What attractions are nearby?

Enjoy nearby activities in the area, from relaxing waterfront parks to vibrant local events, making your stay in this destination both memorable and convenient.

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Family Activities

  • Key West Butterfly & Nature Conservatory: You can enjoy a family visit to this lush conservatory, where vibrant butterflies flutter freely among tropical plants, offering an interactive nature experience.
  • Theatre of the Sea Marine Park: Spend a day exploring marine life through engaging shows and animal encounters that captivate children and adults alike in this popular oceanarium nearby.
  • Fort Zachary Taylor Historic State Park: Discover a blend of history and outdoor fun with picnicking, swimming, and exploring the historic fort within this scenic waterfront park.
  • Southernmost Point Buoy: Snap memorable family photos at this iconic marker, celebrating your location’s unique spot at the southern tip of the mainland United States.
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Adult Activities

  • Sunset Sailing Tours: Experience the breathtaking sunsets over the region’s waters with a private sailing tour that offers both relaxation and scenic beauty.
  • Fishing Excursions: Embark on a guided fishing adventure to enjoy the abundant marine life, perfect for unwinding and connecting with nature here.
  • Wildlife Watching in the Area: Discover the diverse local fauna on eco-tours designed to showcase the region’s unique birdlife and aquatic species.
  • Kayaking Adventures: Paddle through calm waters of nearby mangroves or coastal areas for an active, immersive experience in this destination's natural surroundings.

Other Places to Stay in The Meadows, FL

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The Meadows Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Flavors: Take advantage of the area's renowned dining options to experience authentic Key West cuisine during your stay.
  • Plan Outdoor Activities: Make the most of the region’s pleasant weather by scheduling water sports or nature walks right from your rental here.
  • Visit Nearby Attractions: Discover local points of interest that showcase the unique charm and culture of this destination to enrich your trip.
  • Optimize Your Booking: Choose a rental by owner for personalized service and direct communication, ensuring a smooth and tailored vacation experience.

Transportation Options

  • Personal Vehicles: Renting or using your own vehicle offers flexible access to the region, making it easy to explore nearby attractions and scenic spots at your own pace.
  • Public Buses: The local bus service provides affordable and convenient transportation options for getting around the area without the need for parking or driving yourself.
  • Ride-Sharing Services: Popular ride-sharing companies operate here, offering quick and reliable transportation for visitors seeking comfort and convenience during their stay.
  • Bicycle Rentals: Cycling is an eco-friendly and leisurely way to explore the area's scenic routes and neighborhoods, with numerous rental shops available nearby.

Local Customs Options

  • Respect for the Local Environment: Visitors are encouraged to preserve the natural beauty of the region by minimizing their ecological footprint during their stay.
  • Celebration of Community Events: Participating in local festivals and gatherings is a cherished tradition that helps you connect with residents of this destination.
  • Emphasis on Casual Hospitality: The area values laid-back interactions and friendly exchanges, reflecting the relaxed lifestyle here.
  • Adherence to Marina and Waterway Etiquette: When enjoying the nearby waters, it's important to follow local boating customs and safety guidelines to respect the community’s maritime traditions.

Frequently Asked Questions About The Meadows Rentals by Owner

1. What are the top vacation rentals in The Meadows?

There are a lot of options in The Meadows. If you plan on staying in the The Meadows 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 Meadows:

2. How many Rentbyowner vacation rentals are available in The Meadows?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 89 in the The Meadows 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 Meadows. 

3. What is the cancellation policy for rentals in this area?

The cancellation policy varies depending on the owner’s specific rental listing. You should review the cancellation terms listed on the property page or contact the owner directly to understand any applicable fees or conditions.

4. Are there any additional fees I should be aware of when booking a rental in this region?

Additional fees such as cleaning fees, security deposits, or service charges are often detailed in the listing. Be sure to carefully read the listing details or reach out to the owner for clarification of any extra costs.

5. How do I confirm the availability of a rental during my desired dates?

Availability can be checked directly through the booking platform by selecting your dates. If you have specific questions about availability, contacting the owner may provide additional insights or assistance.

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

Most rentals include essential amenities such as Wi-Fi, air conditioning, and kitchen facilities. For a complete list of what’s included, review the property’s listing details or contact the owner directly.

7. What is the process for checking in and out of a rental in this destination?

Check-in and check-out procedures are usually outlined on the listing or communicated by the owner. These may involve key exchange methods, access codes, or meeting times, which you can clarify before your arrival for a smooth stay.

More Rentals You May Like Near The Meadows

More Top-Rated Rentals by Owner in The Meadows Area