Midtown vacation rentals

We found 1,772 vacation rentals — enter your dates for availability

Welcome to the enchanting allure of Key West, where sun-kissed beaches, vibrant streets, and rich history blend seamlessly to create an unforgettable escape. Stroll along Duval Street, savor local cuisine, and capture memories at the iconic Southernmost Point. With a variety of accommodations in Midtown—from cozy cottages to stylish condos—your group will find the perfect home base for adventure. Embrace the comfort and convenience of a vacation rental, where you can unwind and create lasting memories together.

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Find out more about Midtown

Why visit Midtown

  • Beautiful Beaches: Midtown offers easy access to pristine beaches, perfect for sunbathing and water activities.
  • Charming Streets: Explore the vibrant streets of New Town, blending tropical vibes with historical charm.
  • Cultural Experiences: Enjoy a variety of excursions and local culture that showcases the unique essence of Key West.
  • Diverse Accommodations: Choose from cozy vacation rentals, stylish condos, or charming cottages to suit your stay.
  • Family-Friendly Atmosphere: Midtown is ideal for families, offering activities that cater to all ages.

Popular types of accommodation around Midtown

Discover the perfect getaway with Midtown vacation rentals, featuring a variety of options to suit every traveler's needs. Whether you're looking for a cozy private vacation home, a stylish condo, or a charming cottage, we've got you covered. Explore our selection of Key West rentals and other vacation homes in Midtown to ensure a memorable stay. Your ideal holiday rental awaits, providing the transparency, savings, and reassurance you deserve.

  • Houses: The top choice for travelers in Midtown, these homes offer spacious accommodations perfect for families, groups, or couples seeking privacy and comfort.
  • Condos: A popular option for those wanting modern amenities and proximity to local attractions, condos provide a stylish and convenient stay.
  • Cottages: Ideal for a quaint getaway, these cozy retreats offer a charming atmosphere for a relaxing vacation.
  • Apartments: A practical choice for solo travelers or couples, apartments combine comfort with a home-like feel in the heart of Midtown.
  • Villas: These upscale properties provide luxury and spaciousness, perfect for those seeking an indulgent experience.**

Top attractions near Midtown

Midtown, Key West, offers a vibrant blend of culture and relaxation, making it ideal for family, business, or city-themed vacations. Explore popular attractions like the beach, historic houses, and lively streets. Whether you're seeking a cultural experience or simply want to soak up the sun, Midtown has something for everyone. Don't miss out on the charm and excitement this unique destination has to offer while planning your trip to Key West, Florida.

  • Duval Street: A vibrant thoroughfare filled with lively bars, eclectic shops, and local eateries, perfect for experiencing the energetic spirit of Key West. It's a hub of nightlife and culture, making it a must-visit for tourists.
  • Southernmost Point: This iconic landmark marks the southernmost point of the continental U.S., featuring a colorful buoy. Visitors can capture memorable photos while soaking in the rich history and culture of the area.
  • Smathers Beach: A beautiful stretch of sandy shoreline ideal for sunbathing, swimming, and water sports. With its relaxed atmosphere and stunning sunsets, it's the perfect spot to unwind and enjoy the Florida sun.

Things to do recommended for couples

Ready for a romantic getaway in Midtown, Key West? Explore the charming streets hand-in-hand, savor a sunset sail on crystal-clear waters, or indulge in a candlelit dinner at a waterfront restaurant. Create unforgettable memories together in this tropical paradise.

Things to do recommended for families

Families can have a great time at the MLK Community Pool & Community Center, located 1 mile from Midtown. This facility offers a fun pool atmosphere with sports and outdoor activities, perfect for creating lasting memories together.

Things to do recommended for groups

Experience the beauty of Key West at the Key West Golf Club, just 3 miles from Midtown, perfect for outdoor enthusiasts. Enjoy a cultural evening at the Waterfront Playhouse, 2 miles away, offering entertainment for all ages. Don’t forget to visit The Kite House, just 1 mile from Midtown.

*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 Midtown

If you're traveling with a group, as a family, with pets, or planning an extended stay, be sure to use the right filters to match your priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Midtown with a group: Think about how many bedrooms you require, as well as any amenities you might want, like a full kitchen or outdoor space for group gatherings. Thankfully, Vrbo allows you to filter for these features and more.
  • Traveling to Midtown with young kids: Traveling with young kids can present some challenges. It's important to prioritize 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 family-friendly attractions.
  • Taking your pets with you to Midtown: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Midtown: If you're in search of 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 think about including amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Midtown

Midtown Key West offers a vibrant blend of adventure and relaxation, perfect for families and business travelers alike. Enjoy easy access to pristine beaches and explore the charming streets of New Town, where tropical vibes meet historical allure. Just a short distance from the lively heart of Key West, Midtown invites you to experience a unique atmosphere filled with excursions and local culture, making it an ideal base for your Florida getaway.

  • Key West: Key West is a vibrant city located on the southernmost point of the continental United States. As an island destination, it offers a unique blend of tropical charm and bustling activity. Visitors flock to Key West for its diverse experiences, ranging from family-friendly attractions to business-themed venues. The city is home to bustling shopping areas and resorts that cater to all types of travelers. Popular local landmarks include beautiful beaches and lively streets, where you can soak up the sun, enjoy water sports, or explore local cuisine.
  • Beachside: Just 0.1 miles from Midtown, Beachside is a picturesque neighborhood that captures the essence of coastal living. This area is perfect for families and beach lovers alike, providing access to sandy shores and recreational activities. Beachside boasts a variety of shopping areas and malls, making it a convenient spot for both leisure and retail therapy. The local attractions include the inviting beach and charming streets, creating an ideal atmosphere for relaxation and family fun.
  • Old Town Key West: Located 0.9 miles from Midtown, Old Town Key West is a historic neighborhood steeped in culture and charm. This area attracts visitors seeking city-themed experiences, as well as family and business-oriented activities. Old Town is known for its quaint shopping areas and resorts, making it a hub for tourists. The nearby attractions include vibrant streets and beautiful beaches, providing endless opportunities to explore the rich history and scenic beauty of Key West.

Best time to go to Midtown

If you're planning a trip to Midtown, 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

Are you hoping to cut costs on your upcoming getaway? One effective strategy is to keep your travel dates flexible, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travels.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is designed to help you plan your journeys with ease. You can create new trips, refine your existing plans, or take a closer look at your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for your convenience. To check out Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Midtown?
In Midtown, vacation houses are the most popular type of rental accommodation, with about 40 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many also come with outdoor spaces such as patios or gardens, superb for relaxation after a day of exploring. Additionally, there are several apartments and condos, which offer a more compact living option while still providing essential amenities for a comfortable stay.
Are there any beach house rentals in Midtown?
In Midtown, Florida, there are approximately 87 beach house rentals available, offering travelers a variety of options for their stay. Most of these rentals are situated in neighborhoods that provide easy access to local attractions and the beautiful nearby coastline. Guests can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation and entertainment. Many properties also feature multiple bedrooms, making them ideal for families or groups looking for a comfortable getaway.
How much does it cost to rent a vacation home in Midtown?
Prices for vacation rentals in Midtown 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 Midtown 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 Midtown vacation house rentals?
You can find great discounts on house rentals in Midtown 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.
What are popular rental amenities in Midtown?
In Midtown, Florida, travelers can expect a variety of popular vacation rental amenities that enhance their stay. Many properties feature fully equipped kitchens, allowing guests to prepare their own meals comfortably. Additionally, coffee and tea makers are commonly available, great for those who enjoy a morning brew. For relaxation and entertainment, a private pool is a sought-after amenity, providing a refreshing retreat on warm days. Many rentals also include outdoor spaces such as decks or patios, where guests can unwind and enjoy the pleasant Florida weather. Onsite parking is typically available, offering convenience for those traveling with vehicles.
Can I find family house rentals in Midtown?
In Midtown, Florida, there are numerous family-friendly house rentals available—about 28 to choose from. This vibrant area is well-suited for families, offering spacious homes with amenities such as full kitchens, large living rooms, and outdoor areas great for children to play. Many properties also come equipped with essentials like Wi-Fi and air conditioning, ensuring a comfortable stay.Visitors can explore nearby attractions, including parks and local dining options that cater to all tastes. The neighborhood's family-friendly atmosphere makes it an excellent destination for those looking to enjoy both relaxation and local culture.
Can I rent a vacation home with a pool or hot tub in Midtown?
In Midtown, Florida, there are numerous vacation homes available for rent that feature pools and hot tubs, with around 36 options to choose from. This vibrant area offers a mix of modern and comfortable accommodations, often equipped with amenities such as private pools, relaxing hot tubs, outdoor spaces for lounging, and fully equipped kitchens that make it easy to enjoy meals at home. Travelers can expect properties with generous living areas, stylish decor, and the convenience of nearby attractions and local dining options.
Are there any Midtown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Midtown 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 book pet-friendly vacation rentals in Midtown?
In Midtown, Florida, there are numerous pet-friendly vacation rentals available, making it a great destination for those traveling with pets. With about 21 options to choose from, travelers can find a variety of accommodations that cater to their needs. Many of these rentals feature amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, allowing guests to enjoy a comfortable stay while accommodating their furry friends.The neighborhood itself has a friendly setting with nearby parks and pet-friendly spaces, superb for leisurely walks and outdoor activities. Visitors can explore local dog parks or enjoy the community's green areas, ensuring that both pets and their owners have plenty of opportunities to relax and play.
Can I find long-stay vacation rentals in Midtown?
A long-stay vacation rental in Midtown 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 Midtown for a vacation rental?
The most popular time to visit Midtown, Florida, is from January to March, with March being the standout month for tourists seeking a vibrant vacation experience. This peak season attracts a diverse crowd eager to enjoy the region's pleasant climate, bustling atmosphere, and variety of outdoor activities. With temperatures typically ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably explore local parks, attend outdoor festivals, and partake in water sports.March offers not just comfortable weather but also a host of events and attractions that cater to adventure seekers and families alike. The longer days and vibrant community events create a lively backdrop for your vacation rental experience, making it an ideal time to immerse yourself in Midtown's charm.For those looking for more budget-friendly options, consider visiting in October. This month allows for a more tranquil experience, where you can enjoy the local sights without the larger crowds. The weather remains warm, and the area's natural beauty shines as the autumn colors start to emerge, great for leisurely strolls and outdoor dining.
Are there any remote work vacation rentals in Midtown?
In Midtown, Florida, there are ample options for remote work vacation rentals, with around 41 available in the area. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces including desks and chairs, and comfortable living areas that cater to productivity while enjoying a change of scenery.Travelers can expect modern accommodations that often feature open layouts, fully equipped kitchens, and outdoor spaces for relaxation. The neighborhood itself is well-connected, making it easy to access local cafes and parks for a refreshing break during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Midtown vacation rental?
Book your Midtown 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 Midtown, Florida, United States of America?
In Midtown, Florida, visitors can enjoy a variety of attractions that highlight the area's charm and culture. The Midtown area is known for its vibrant shopping scene, with numerous boutiques and local shops offering unique goods. The nearby parks, such as Lake Ella Park, provide recreational opportunities where visitors can stroll along the picturesque lake, enjoy a picnic, or participate in outdoor activities.Additionally, Midtown is close to the Florida State University campus, which offers cultural events and athletic competitions throughout the year. The area features a selection of dining options, ranging from casual eateries to upscale restaurants, allowing guests to experience local flavors.
Can I change or cancel my Midtown home rental booking on Vrbo?
To find Midtown 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 Midtown 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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