The Meadows holiday lettings

We found 872 holiday rentals — enter your dates for availability

Discover a selection of 31 homes and other holiday rentals in The Meadows that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

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Why visit The Meadows

  • Rich history: Explore the Key West Museum and other historic houses that highlight the area's fascinating past.
  • Charming neighbourhood: The Meadows features picturesque streets perfect for leisurely strolls and discovering local charm.
  • Beautiful beaches: Enjoy sunbathing and water activities at some of the stunning nearby beaches.
  • Diverse accommodation: Choose from charming cottages, modern condos, or spacious homes tailored to your needs.
  • Family-friendly activities: The Meadows offers a variety of attractions suitable for visitors of all ages.

Popular types of accommodation around The Meadows

The Meadows offers a delightful selection of vacation rentals, perfect for your next getaway. Whether you’re seeking a charming cottage, a modern condo, or a spacious private vacation home, you’ll find the ideal accommodation to suit your needs. With our transparent information and commitment to savings, planning your escape to The Meadows or Key West has never been easier. Explore the best meadows vacation rentals today!

  • Houses: A favourite among travellers to The Meadows, these homes offer ample space and privacy, making them ideal for families or groups.
  • Condos: The second most sought-after option, condos provide modern amenities and are often conveniently located near attractions.
  • Cottages: These quaint and charming accommodations are perfect for a cosy getaway, offering a homey atmosphere.
  • Apartments: A practical choice for solo travellers or couples, apartments combine comfort with independence.
  • Villas: Luxurious and spacious, villas are great for those seeking an upscale experience during their stay.**

Top attractions near The Meadows

The Meadows in Key West, Florida, is an excellent destination for family, city-themed, or business holidays. Visitors can explore a variety of attractions, including beautiful beaches, charming streets, and historic houses, all catering to those seeking culture and a vibrant city experience. A notable point of interest is the Key West Museum, which offers a glimpse into the area's rich history. There's something for everyone to enjoy in this delightful locale.

  • Duval Street: A lively thoroughfare known for its vibrant atmosphere, offering an eclectic mix of shops, restaurants, and nightlife. Stroll along the street to soak in the local culture and enjoy street performances.
  • Ernest Hemingway Home and Museum: A charming historic house that once belonged to the famous author. Explore the lush gardens and learn about Hemingway's life and literary contributions in this culturally rich setting.
  • South Beach: A stunning stretch of sandy shoreline perfect for sunbathing, swimming, and water sports. Relax on the beach while enjoying the warm Florida sun and picturesque ocean views.

Things to do recommended for couples

For a romantic getaway in The Meadows, Key West, enjoy a sunset sail on the azure waters, wander hand-in-hand through lush gardens at the Ernest Hemingway Home, or savour a candlelit dinner at a charming seafood restaurant. Each moment promises to be enchanting for couples.

Things to do recommended for families

Families will love a visit to the MLK Community Pool & Community Centre, located 559m from The Meadows. This inviting outdoor space offers a fun atmosphere for swimming and engaging in sports, perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a round of golf at Key West Golf Club, only 1.9km from The Meadows. For a cultural evening, visit the Key West Burlesque Theater, a mere 124m away. Don't forget to explore The Kite House, located 311m away for some unique shopping.

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

If you're travelling with a group, family, or pets, or if you're considering longer stays, it's essential to filter your search according to your key priorities. Here are some helpful Vrbo booking tips for 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. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to The Meadows with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to The Meadows: For many, a family holiday feels incomplete without their furry companion. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting The Meadows: If you’re in search of holiday rentals offering 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 accommodations. Don’t forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search.

Where to stay near The Meadows

The Meadows in Key West, Florida, offers a delightful blend of family-friendly activities and vibrant city life. This charming neighbourhood is perfect for exploring tropical surroundings, rich history, and romantic spots. Wander through nearby areas to discover unique local rentals and immerse yourself in the captivating atmosphere of Key West's diverse neighbourhoods. Whether you’re planning a relaxing escape or an adventurous holiday, The Meadows is an ideal base for your Floridian getaway.

  • Key West: Key West is a vibrant city renowned for its laid-back island atmosphere, situated 497m from The Meadows. With its beautiful beaches and lively streets, it offers a unique blend of family-friendly activities and cultural experiences. Visitors can indulge in shopping at local boutiques or enjoy the bustling mall centres. Key landmarks include stunning beaches ideal for family outings, making it a perfect destination for both relaxation and exploration. The city’s rich history and lively nightlife further enhance the travel experience, inviting tourists to enjoy everything from seaside dining to water sports.
  • Old Town Key West: Located a mere 311m from The Meadows, Old Town Key West is a charming neighbourhood filled with historic architecture and a lively atmosphere. This area is perfect for families, offering a mix of shopping areas and resorts that cater to various interests. Explore the picturesque streets lined with quaint shops and cafes, and take advantage of the proximity to beautiful beaches that are perfect for a day out with loved ones. With its blend of history and modern conveniences, Old Town is a delightful spot for both leisurely strolls and engaging activities.
  • Key West Historic District: Just 311m from The Meadows, the Key West Historic District is a treasure trove of culture and history. This neighbourhood attracts visitors seeking a city-themed experience, complete with unique shopping options and resort facilities. Meander through historic streets and soak in the vibrant atmosphere, while also enjoying access to stunning beaches perfect for families. The district’s rich heritage and lively arts scene make it an ideal destination for those wanting to immerse themselves in the local culture and history while enjoying a variety of activities.

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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides you with a convenient platform to plan new getaways, manage your existing arrangements, or keep track of your bookings. The properties you've saved or reserved are now neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in The Meadows?
Prices for holiday 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 holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in The Meadows with parking available—perfect for families or travellers 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 holiday rentals in The Meadows?
A long-stay holiday rental in The Meadows is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
How early should I book a The Meadows holiday rental?
Book your The Meadows holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my The Meadows home rental booking on Vrbo?
To find The Meadows holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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