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Best Vacation Homes in The Meadows

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The Meadows Pet Friendly Vacation Rentals

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The Meadows Large Vacation Homes

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

Where are the best neighborhoods to stay in The Meadows?

When choosing where to stay in Key West, Florida, exploring neighborhoods like The Meadows offers a fantastic opportunity to experience the local charm and relaxed island lifestyle. Located in a peaceful part of the city, The Meadows provides convenient access to the vibrant attractions and stunning waterfronts of Key West, making it an ideal base for your tropical getaway. With a range of well-maintained vacation rentals in this area, you can enjoy a comfortable and authentic experience while staying close to the heart of the island’s unique character.

Key West Historic District

In this vibrant area, you can immerse yourself in the rich history and charming architecture that define the region's unique character. Staying nearby allows easy access to the historic charm that makes this destination truly special.

View 2504+ Rentals in Key West Historic District

Old Town

Nestled in the heart of the region, Old Town offers colorful streets and a lively atmosphere, perfect for exploring local culture and enjoying convenient access to popular attractions.

View 2436+ Rentals in Old Town

Meadows

This tranquil neighborhood provides a peaceful retreat while still being close to key points of interest, making it an ideal choice for those seeking relaxation amidst the area's natural beauty.

View 88+ Rentals in Meadows

White St. Gallery

Located within walking distance of the White Street Gallery District, this neighborhood offers a blend of artistic ambiance and easy access to local galleries, enhancing your cultural experience.

View 3797+ Rentals in White St. Gallery

Best Times to Visit The Meadows

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, so consider planning your trip during the region's most favorable seasons for pleasant weather and enjoyable outdoor activities.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can experience the warm and inviting climate that makes this destination a popular choice for escaping colder weather elsewhere.

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

Springtime draws visitors seeking pleasant weather and vibrant scenery, making it an ideal season for enjoying the area's outdoor activities and exploring comfortably.

Average Temperature Daytime: 78°F - Nighttime: 70°F

Off-Season Highlights

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Summer (June to August)

The summer period sees slightly fewer visitors, providing a quieter atmosphere while still offering warm temperatures perfect for beach days and relaxation.

Average Temperature Daytime: 88°F - Nighttime: 80°F
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Fall (September to November)

Fall offers a more tranquil setting, with fewer crowds and mild weather, making it a great time to enjoy peaceful getaways along the coast.

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

Weekly Weather Forecast for The Meadows

How to Book Your The Meadows 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 The Meadows

More Top-Rated Vacation Rentals in The Meadows 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 pool to relax after exploring the local scenery.
  • Take advantage of spacious patios or decks for dining and entertaining outdoors.
  • Benefit from lush, landscaped gardens that provide privacy and natural beauty.
  • Make use of outdoor grills or barbecue setups for casual meals with family and friends.
  • Relax in comfortable lounge areas designed for enjoying the warm Florida sun.
  • Utilize outdoor showers or hammocks to unwind in a tranquil setting.
  • Explore nearby walking paths or bike-friendly loops for outdoor recreation in the area.

Top Attractions Around The Meadows

What attractions are nearby?

When staying here, you'll have the opportunity to explore nearby beaches, charming local shops, and vibrant dining options that make this destination a perfect base for enjoying all that the region has to offer.

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Family Activities

  • Key West Butterfly & Nature Conservatory: Discover a magical world of butterflies and tropical birds that enchant children and adults alike, making it a memorable family outing here.
  • Fort Zachary Taylor Historic State Park: Enjoy a relaxing day at this scenic park with shaded picnic areas, sandy beaches, and opportunities for swimming and exploring historic forts.
  • The Key West Aquarium: Experience interactive exhibits and marine animal encounters that engage young explorers in the region's vibrant aquatic life.
  • Smathers Beach: Spend your day lounging on the soft sands or trying water activities at this popular beach destination close to the area’s vacation rentals.
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Adult Activities

  • Explore the vibrant local art scene: Discover unique galleries and street art that reflect the creative spirit of this island destination.
  • Enjoy water-based activities: Embark on snorkeling, kayaking, or paddleboarding adventures in the crystal-clear waters surrounding the area.
  • Visit historic sites and landmarks: Immerse yourself in the region’s rich history by touring notable museums and preserved architecture.
  • Savor fresh seafood at waterfront restaurants: Indulge in delicious coastal cuisine while enjoying scenic views that highlight the area's nautical charm.

Other Places to Stay in The Meadows, FL

The Unitarian Universalist Fellowship of Key West
The Unitarian Universalist Fellowship of Key West Vacation Rentals
Meadows
Meadows Vacation Rentals
More Places to Stay Near The Meadows

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.
  • Visit Nearby Beaches: Make time to relax at the beautiful beaches close to your vacation rentals, soaking in the sunshine and tranquil ocean views.
  • Discover Unique Local Events: Check out community events and festivals that highlight the vibrant culture and lively spirit here in this destination.
  • Plan Outdoor Activities: Enjoy outdoor adventures like fishing, boating, or exploring scenic trails to fully immerse yourself in the region's natural beauty.

Transportation Options

  • Car Rentals: Renting a car is one of the most flexible ways to explore the region and enjoy your stay here at your own pace.
  • Public Transit: The local bus system offers affordable and reliable transportation options to key destinations around the area.
  • Bike Rentals: Biking is a popular choice for getting around here, providing an eco-friendly way to experience the scenery up close.
  • Taxi and Rideshare Services: Taxis and rideshare apps like Uber or Lyft provide convenient door-to-door service throughout this destination.

Local Customs Options

  • Respect for Waterfront Heritage: Locals in this area honor a long-standing tradition of fishing and maritime activities that are central to their way of life.
  • Celebration of Art and Music: The community embraces vibrant art festivals and live music events, reflecting the region’s rich cultural heritage and laid-back vibe.
  • Eco-Friendly Practices: Sustainability is important here, with many residents supporting eco-conscious initiatives to preserve the area's natural beauty.
  • Balancing Relaxation and Festivity: Visitors often partake in a relaxed pace of life while enjoying lively local events, making it ideal for those seeking both tranquility and community spirit.

Frequently Asked Questions About The Meadows?

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 vacation rentals have private pools in The Meadows?

There are 30 vacation rentals with private pools near The Meadows. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in The Meadows are best for families?

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

4. 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 136 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. 

5. What is the cancellation policy for booking a vacation rental here?

Cancellation policies vary depending on the individual property listing. You should review the specific property's cancellation terms on its page or contact the host directly to understand the conditions and any potential fees.

6. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are set by each property owner. Details are typically listed in the booking description, so it's recommended to confirm these times during your reservation process or by reaching out to the host.

7. How do I ensure the property has the amenities I need for my stay?

Each property listing includes a detailed list of available amenities. For any special requirements, you can contact the host beforehand to confirm that the property meets your needs.

8. Is there a secure way to pay for my booking?

Payments are processed through a secure platform integrated into the booking website. It’s best to use this system to protect your financial information and ensure a smooth transaction.

9. What should I do if I encounter an issue during my stay or need assistance?

In case of any problems, you should contact the property host directly first. If you require further support, the booking platform offers customer service to assist with resolving issues related to your reservation or stay.

The Meadows Top Rated Vacation Rentals

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