The Meadows vacation rentals

We found 877 vacation rentals — enter your dates for availability

Discover a selection of 31 homes and other vacation rentals in The Meadows that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

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Find out more about The Meadows

Why visit The Meadows

  • Beautiful Beaches: Enjoy sun-soaked days at stunning beaches, perfect for relaxing and water sports.
  • Historic Attractions: Discover charming historic houses and landmarks that showcase Key West's rich history.
  • Tropical Atmosphere: Experience the lush greenery and tropical environment that defines The Meadows.
  • Cultural Experiences: Immerse yourself in vibrant local culture with art, music, and unique dining options.
  • Variety of Accommodations: Choose from inviting vacation rentals, including private homes, condos, and cottages.

Popular types of accommodation around The Meadows

If you're exploring vacation rentals in The Meadows, you're in for a treat. Our most sought-after accommodations include Houses, Condos, and Cottages. Whether you're looking for spacious meadows apartments or cozy Acacia Meadows, you'll find fantastic amenities, inviting dining areas, and comfortable residence rooms to enhance your stay. Enjoy the perfect blend of relaxation and adventure in this charming destination.

  • Houses: The top choice for visitors to The Meadows, these homes offer spacious and comfortable living, perfect for families or groups.
  • Condos: A popular option, condos provide modern amenities and convenient locations, ideal for couples and small families.
  • Cottages: These charming retreats offer a cozy atmosphere, perfect for a romantic getaway or a peaceful solo trip.
  • Apartments: A practical choice for those seeking a home-like feel, apartments are great for longer stays with all the essentials.
  • Villas: Luxurious and spacious, villas offer an upscale experience for those wanting extra comfort and privacy.**

Top attractions near The Meadows

The Meadows in Key West, Florida, is an ideal destination for family vacations, business trips, and city-themed getaways. Visitors can explore a variety of attractions including beautiful beaches, historic houses, and vibrant streets. Whether you're seeking cultural experiences, a fun day at the beach, or the charm of city life, The Meadows offers something for everyone to enjoy during their stay.

  • Duval Street: A vibrant hub of Key West, Duval Street is filled with lively bars, eclectic shops, and delicious restaurants, offering a quintessential Floridian experience just 0.7 miles from The Meadows.
  • Ernest Hemingway Home and Museum: Explore the fascinating life of the acclaimed author in this beautiful historic house, located 0.8 miles away, where you can admire lush gardens and learn about Hemingway's literary legacy.
  • South Beach: A stunning stretch of sandy shore, South Beach invites you to relax and soak up the sun, just 0.8 miles from The Meadows, perfect for swimming and enjoying the vibrant beach atmosphere.

Things to do recommended for couples

For a romantic getaway in The Meadows, Key West, indulge in sunset sails on a catamaran or explore the charming streets by bicycle. Enjoy a cozy dinner at a waterfront restaurant and don't miss a leisurely stroll along the beach under the stars.

Things to do recommended for families

Families visiting The Meadows in Key West can have a splash-tastic day at the MLK Community Pool & Community Center, just 0.9 miles away. Enjoy sports and outdoor activities in a vibrant, family-friendly atmosphere perfect for making lasting memories.

Things to do recommended for groups

Experience the laid-back vibes of Key West by teeing off at the Key West Golf Club, just 3 miles away. Enjoy a night of culture and entertainment at the Waterfront Playhouse, only 1 mile from The Meadows, or shop for unique finds at The Kite House, a half-mile away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around The Meadows

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your search accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to The Meadows with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to The Meadows with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for the whole family.
  • Taking your pets with you to The Meadows: For many families, a vacation just isn’t the same without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting The Meadows: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near The Meadows

The Meadows in Key West offers a perfect blend of family-friendly activities and romantic excursions. Surrounded by beautiful trees and a tropical atmosphere, this neighborhood provides easy access to the charm of downtown Key West. Explore nearby historical sites and enjoy the vibrant local culture, making it an ideal spot for both relaxation and adventure. With excellent property ratings, you're sure to find the perfect place to call home during your stay.

  • Key West: Key West is a vibrant city known for its stunning island charm and laid-back atmosphere. Nestled at the southernmost point of the continental United States, this beautiful locale offers travelers a plethora of experiences, from family-friendly activities to business-oriented events. Visitors can enjoy a variety of shopping areas, resort accommodations, and beautiful beaches, perfect for sunbathing and water sports. Key West is also famous for its lively streets filled with unique shops and restaurants, making it an ideal destination for both relaxation and exploration.
  • Old Town Key West: Located a mere half-mile from The Meadows, Old Town Key West is a historic neighborhood that encapsulates the essence of island life. This charming area is renowned for its picturesque streets lined with colorful architecture, local shops, and delightful eateries. Ideal for families and business travelers alike, Old Town offers a vibrant atmosphere with easy access to shopping malls and resorts. Visitors can unwind at the nearby beaches or stroll along the streets to soak in the local culture while enjoying the tropical ambiance.
  • Key West Historic District: Just a half-mile from The Meadows, the Key West Historic District is a must-visit for those interested in the island's rich history and culture. This neighborhood features beautifully preserved buildings and landmarks that tell the story of Key West's past. Travelers can explore shopping areas and resorts while enjoying the area's family-friendly environment. With its close proximity to stunning beaches and inviting streets, the Historic District offers a perfect blend of relaxation and cultural exploration, making it a favorite among visitors.

Best time to go to The Meadows

If you're planning a trip to The Meadows, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnySlightly HighAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnySlightly HighAverage
March73.4°F (23.0°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly Low
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnySlightly LowSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowAverage
November76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
December73.9°F (23.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you interested in saving on your upcoming vacation? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to customize your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and keep your bookings organized. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a vacation home in The Meadows?
Prices for vacation rentals in The Meadows vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in The Meadows to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for The Meadows vacation house rentals?
You can find great discounts on house rentals in The Meadows on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any The Meadows vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in The Meadows with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in The Meadows?
A long-stay vacation rental in The Meadows is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit The Meadows for a vacation rental?
March is the most popular time to visit The Meadows, as travelers flock to this beautiful area to enjoy the pleasant climate and vibrant community events. The peak season spans from January to March, drawing visitors eager to take advantage of outdoor activities such as golfing, biking, and enjoying the stunning Florida sunshine. With temperatures typically ranging from the mid-60s to low 80s Fahrenheit, you'll find the weather ideal for exploration and relaxation alike.

During this peak season, The Meadows buzzes with energy. Visitors can partake in various activities, from leisurely strolls through lush parks to engaging in water sports nearby. The community's welcoming atmosphere makes it a superb destination for families and adventure seekers looking to make lasting memories.

For those seeking a more budget-friendly option, consider planning your visit in October. While this month is quieter, it still offers the opportunity to enjoy the natural beauty of the area, with fewer crowds and the chance to explore at your own pace. The fall weather remains warm, allowing for comfortable outdoor adventures and scenic drives.

Ultimately, the best time to book a vacation rental in The Meadows will depend on your preferences.
How early should I book a The Meadows vacation rental?
Book your The Meadows vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in The Meadows?
In The Meadows, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The Meadows neighborhood itself is known for its picturesque landscapes, featuring lush greenery and serene lakes, making it ideal for outdoor activities like walking, jogging, and biking. Nearby, you can explore the scenic trails at the nearby Nathan Benderson Park, which offers opportunities for paddleboarding and rowing on its beautiful lake.

Additionally, the area provides convenient access to the vibrant cultural scene in downtown Sarasota, where attractions like the Ringling Museum of Art and the historic Sarasota Opera House can be found. For those interested in shopping and dining, the nearby UTC Mall features a range of retail options and restaurants to suit various tastes.
Can I change or cancel my The Meadows home rental booking on Vrbo?
To find The Meadows vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the The Meadows vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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