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Midtown vacation rentals

We found 1,856 vacation rentals — enter your dates for availability

Discover a selection of 45 homes and other vacation rentals in Midtown that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a pool. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

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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.

Save more with One Key

Reserve an eligible 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, OneKey, you can easily access member discounts and earn as well as redeem OneKeyCash on qualifying reservations. Sign up today to start enjoying savings.

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 approximately 11 available in the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable and home-like environment. Additionally, there are several condos in the vicinity that offer a more compact living option, often with amenities like pools, fitness centers, and access to communal outdoor spaces.
Are there any beach house rentals in Midtown?
In Midtown, Florida, there are approximately 39 beach house rentals available, providing a variety of options for travelers. These rentals typically feature spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation, such as patios or decks where guests can enjoy the warm Florida weather. Many of the properties are located near local attractions, including parks and family-friendly venues, making it convenient for guests to explore the area.
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, popular vacation rental amenities include private pools, with many properties featuring heated options to ensure comfort year-round. Travelers can expect fully equipped kitchens, allowing for convenient meal preparation during their stay. Additionally, most rentals come with patios, providing outdoor spaces to relax and enjoy the pleasant Florida weather. Some accommodations may also include amenities like blenders for those looking to whip up smoothies or cocktails.
Are there any family house rentals in Midtown?
In Midtown, Florida, there are several family-friendly house rentals available, with about 11 options to choose from. This vibrant area offers a mix of spacious homes that cater well to families. Many of these properties feature ample living spaces, full kitchens for preparing meals, and outdoor areas where children can safely play and explore.

Visitors will appreciate amenities such as Wi-Fi and air conditioning, ensuring a comfortable environment during their stay. The neighborhood is conveniently located near parks and recreational areas, making it easy for families to enjoy outdoor activities. Additionally, local attractions and dining options are just a short drive away, adding to the convenience and enjoyment of your visit.
Can I rent a vacation home with a pool or hot tub in Midtown?
In Midtown, Florida, there are several vacation homes available for rent that feature pools and hot tubs, with around 12 options to choose from. This area offers a mix of contemporary and traditional properties, often situated in family-friendly neighborhoods. Travelers can expect a variety of amenities in these rentals, including private pools for cooling off on warm days, hot tubs for relaxation, and outdoor spaces great for barbecues and gatherings. Many homes typically include fully equipped kitchens, spacious living areas, and air conditioning, ensuring a comfortable stay.
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.
Are there pet-friendly vacation rentals in Midtown?
In Midtown, Florida, there are several pet-friendly vacation rentals available for travelers looking to explore the area with their furry companions. Many of these rentals typically offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas. Some properties may also feature outdoor spaces like patios or decks, great for relaxing after a day out.

The neighborhood is conveniently located near several parks, providing ample opportunities for walks and playtime with pets. Local parks often include walking trails and open green spaces, making it a great choice for pet owners who enjoy outdoor activities.
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 best time to visit Midtown, Florida, is during the peak season from January to March, with March being particularly popular among travelers. This vibrant period attracts visitors eager to enjoy the warm climate and partake in outdoor activities, making it an ideal time for those who appreciate sunshine and convenience.

During this peak season, temperatures typically range from the mid-50s to the low 80s Fahrenheit, providing a comfortable environment for sightseeing and exploring the area's attractions. Travelers can take advantage of the pleasant weather to stroll through local parks, visit nearby beaches, or indulge in outdoor dining at charming restaurants.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere, allowing you to explore Midtown at a more leisurely pace. While the temperatures are still pleasant, you can enjoy the benefits of fewer crowds and often find better deals on vacation rentals.

Ultimately, your ideal time to visit Midtown will depend on whether you prefer the lively energy of peak season or the peaceful charm of the shoulder months.
Are there any remote work vacation rentals in Midtown?
In Midtown, Florida, there are several remote work vacation rentals available—specifically around 12 options to choose from. This vibrant neighborhood is known for its convenient access to local amenities and attractions, making it an ideal location for those looking to blend work and leisure. Many of these rentals come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated desks, ergonomic chairs, and even computer monitors, providing a comfortable workspace for travelers.

The area features a mix of modern apartments and cozy homes, often with additional amenities like full kitchens and outdoor spaces, which are superb for relaxation after a productive day. Midtown also offers proximity to parks, shopping centers, and dining options, ensuring that guests can enjoy a balanced lifestyle during their stay. 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.
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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