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  3. Key West
  4. Meadows
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Discover Your Perfect Meadows Cottage Rentals

Meadows Cottage Rentals

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9.0 (1012 Reviews)
Bed & Breakfast
Authors of Key West Guest House
  • Air Conditioner
  • Pool
  • TV
View Availability
|
9.5 (7 Reviews)
Apartment
Heron Hideaway
  • Air Conditioner
  • Parking
  • Pool
View Availability

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Why Choose Rent By Owner for your Meadows Cottage Rentals?

What makes our Cottage 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 Meadows Cottage Rentals

Where are the best neighborhoods to stay in Meadows?

When choosing where to stay in Meadows, Key West, you’ll find charming neighborhoods that offer a peaceful retreat close to local attractions. Opt for a location that provides easy access to the vibrant atmosphere of Key West, while still maintaining a quiet, relaxed ambiance. These neighborhoods are ideal for experiencing authentic island life with the convenience of nearby amenities and scenic views.

Old Town

In the heart of the region, Old Town offers a vibrant atmosphere with historical charm, making it an ideal spot to find cozy cottages close to local attractions and cultural sites. Staying here provides easy access to the area's best dining, shopping, and waterfront views for a memorable getaway.

View 2371+ Rentals in Old Town

The Meadows

This tranquil neighborhood is perfect if you seek a peaceful retreat within the region, with charming cottages nestled amidst lush greenery. Here, you'll enjoy a relaxing ambiance while remaining conveniently close to Key West's scenic parks and leisurely pursuits.

View 100+ Rentals in The Meadows

White Street Gallery District

Known for its artistic flair, the White Street Gallery District features stylish cottages near local art galleries and cultural hubs. It’s a great choice for those looking to immerse themselves in the creative spirit of the region while enjoying comfortable accommodations.

View 24+ Rentals in White Street Gallery District

Best Times to Visit Meadows

When should you plan your Cottage Rentals stay?

Choosing the best time to visit this scenic destination depends on your preferences for weather and local events, ensuring you enjoy your stay in the region’s cottages at their most inviting and comfortable throughout the year.

Peak Season Highlights

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Winter (December to February)

During the winter months, you'll experience the warmest and most pleasant weather in this destination, making it an ideal time for outdoor activities and relaxation in the region's cottages.

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

Spring brings vibrant blooms and comfortable temperatures, perfect for enjoying your stay here while avoiding the peak summer crowds.

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

Off-Season Highlights

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Summer (June to August)

While summer offers hotter and more humid weather, it is also less crowded, providing a peaceful atmosphere to explore this area’s cottages at a relaxed pace.

Average Temperature Daytime: 88°F - 92°F - Nighttime: 75°F - 78°F
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Fall (September to November)

Fall features cooler temperatures and fewer visitors, making it an excellent time to enjoy the tranquil ambiance of the region’s cottages.

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

Weekly Weather Forecast for Meadows

How to Book Your Meadows Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage 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 Meadows

More Top-Rated Cottage Rentals in Meadows Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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 access to private outdoor pools that provide a relaxing retreat amidst the tropical climate.
  • Take advantage of well-maintained barbecue areas perfect for casual outdoor dining with family and friends.
  • Relax in landscaped gardens or lush patios designed to enhance your outdoor experience.
  • Make the most of spacious decks or verandas for lounging and soaking up the sunshine.
  • Utilize outdoor showers that offer convenient rinsing after beach days or water activities.
  • Benefit from on-site parking facilities, making your arrival and exploration effortless.
  • Explore nearby walking paths or outdoor recreational areas to enjoy the scenic surroundings of the region.

Top Attractions Around Meadows

What attractions are nearby?

While staying in this charming area, you can enjoy a variety of activities nearby, including exploring local beaches, engaging in water sports, and discovering vibrant art galleries that showcase the region's unique culture and natural beauty.

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Family Activities

  • Beach Day Adventures: You can spend a fun-filled day soaking up the sun and building sandcastles at one of the area’s beautiful beaches, perfect for family relaxation and play.
  • Wildlife Viewing Excursions: Take your family on guided wildlife tours here to observe local bird species and marine life in their natural habitat.
  • Water Sports Activities: Engage in family-friendly water sports such as kayaking or paddleboarding to enjoy the warm waters and scenic views of this destination.
  • Local Nature Trails: Explore scenic nature trails that are suitable for all ages, offering opportunities for both education and outdoor adventure in the region.
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Adult Activities

  • Sunset Sailing Tours Experience an unforgettable sunset cruise along the waters surrounding this vibrant destination, perfect for relaxing and taking in the scenic views.
  • Kayaking and Paddleboarding Explore the calm, clear waters with kayaking or paddleboarding, offering a serene way to enjoy the region’s natural beauty firsthand.
  • Historic Landmarks Tours Discover the area's rich history by visiting notable landmarks and enjoying guided tours that highlight its unique cultural heritage.
  • Fine Dining Experiences Indulge in culinary delights at local restaurants serving fresh seafood and regional specialties, ideal for a memorable evening out.

Other Places to Stay in Meadows, FL

The Unitarian Universalist Fellowship of Key West
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Meadows Travel Tips

How Can You Make the Most of Your Stay?

  • Embrace Local Experiences: Take advantage of the area's vibrant culture and enjoy exploring the local art, cuisine, and festivals to truly immerse yourself in this destination.
  • Plan Outdoor Activities: Make the most of the region's beautiful natural surroundings by scheduling outdoor activities such as boating, fishing, or relaxing on nearby beaches.
  • Select a Convenient Location: Choose a cottage that offers easy access to key attractions and amenities within the area to maximize your leisure time and convenience.
  • Respect the Community: Be mindful of local customs and environment to ensure a respectful and enjoyable stay in this welcoming destination.

Transportation Options

  • Rental Cars: Renting a car offers the flexibility to explore all corners of this destination at your own pace, with numerous rental agencies conveniently located nearby.
  • Public Transportation: The local bus system provides an affordable and reliable way to get around the region, connecting you to key points of interest effortlessly.
  • Bike Rentals: For a scenic and eco-friendly option, bike rentals are widely available, allowing you to enjoy the natural beauty of the area on your own schedule.
  • Taxis and Rideshares: Taxis and rideshare services provide quick, convenient transportation for short trips or when you'd prefer not to drive yourself.

Local Customs Options

  • Respect for the Local Environment: Visitors are encouraged to honor the region's natural beauty by avoiding littering and participating in conservation efforts.
  • Greeting Traditions: Friendly gestures such as a simple "hello" or a tip of the hat are customary when meeting locals here, reflecting the area's welcoming spirit.
  • Celebration of Festive Events: Participating in community festivals and parades provides an authentic experience and a chance to connect with the local culture.
  • Beach Etiquette: Maintaining quiet and respecting others’ space at public beaches is highly valued in this coastal destination, ensuring everyone enjoys the serene atmosphere.

Frequently Asked Questions About Meadows Rental Cottages

1. What are the top Cottages in Meadows?

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

2. How many Cottages are available in Meadows?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Meadows area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Meadows. 

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

The cancellation policy varies by listing. You should review the specific terms on each cottage's page or contact the owner directly for detailed information regarding cancellations and refunds.

4. Are there any additional fees I should be aware of when booking a cottage?

Additional fees such as cleaning fees, service charges, or taxes are commonly listed in the property details. Be sure to check these details before completing your reservation with the owner’s specified policies.

5. How do I find a cottage that suits my needs in the region?

You can filter search results based on your preferences, including amenities, size, and location within the destination. Contact owners for further questions to ensure the property meets your requirements.

6. Is it possible to modify or cancel my booking if my plans change?

Changes and cancellations are subject to the individual owner’s policies. Review these terms carefully on the listing and reach out directly to the owner if you need assistance or have specific concerns.

7. What amenities can I expect from cottages in this destination?

Many cottages offer features like Wi-Fi, kitchens, outdoor spaces, and air conditioning. Check the specific listing to confirm which amenities are included to enhance your stay.

More Rentals You May Like Near Meadows

10.0 (1 Review)
Apartment
Heron Hideaway
  • Air Conditioner
  • Parking
  • Pool
View Availability

People Visiting Meadows Also Like

More Top-Rated Cottage Rentals in Meadows Area