Midtown vacation rentals

We found 1,769 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 accommodation in Midtown?
Condos are the most popular type of vacation rental in Midtown, according to our data. Even if you have a different idea about what you'd like, Vrbo has vacation homes in all shapes and sizes. Take a look at our options to find your perfect Midtown pad.
How much does it cost to rent a vacation rental in Midtown?
The average price for a vacation rental in Midtown is determined by several factors, like season, property type and length of stay. Whether you're looking for a sprawling villa with a pool or a comfy cabin for just you and the kids, just add your dates of travel to find some great-value stays.
How much does it cost to rent a beach house in Midtown?
The average price for a vacation home near the beach in Midtown depends on when you're visiting the area and the size and type of property you're looking for. You can find prices quickly and easily on Vrbo by entering your destination and travel dates. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in Midtown?
Yes. There are. You'll have a choice of 40 vacation rentals that cater to pets in Midtown. Several of our pet-friendly vacation rentals even come with a backyard for your fur baby to have fun in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Midtown?
Mark the "pool" box in our handy filter tool and you can choose from 32 houses with private pools in Midtown on Vrbo. Ball games, gentle soak or noodle joust? How you spend your free time is up to you when your vacation home boasts a swimming pool.
What are popular rental amenities in Midtown?
A nearby waterfront, an ocean view and a chef top the list of most popular rental amenities in Midtown. Whether you're traveling on your own, with your better half or a bunch of friends, Vrbo will help you find a vacation rental that suits your style with all the extras you're looking for.
Are there large group vacation rentals in Midtown?
Midtown has four vacation properties that can accommodate 10 or more guests. These properties come with the space and privacy you need to share good times with your favorite people.
Are there vacation rentals in Midtown that welcome kids?
Bring the whole family together for fun-filled adventures in Midtown at one of our 38 family-friendly properties. Many of these stays provide conveniences that are ideally suited to trips with youngsters, including dining rooms, extra bedrooms and private pools. Just click on the "Properties good for families" filter and choose your favorite option.
Are there one-bedroom vacation rentals in Midtown?
You'll find three one-bedroom properties in Midtown to select from. A one-bedroom vacation property is a superb choice if it's only you and your partner or if you're vacationing alone. Add in more space, convenience and privacy compared to a hotel, and you've got yourself a memorable getaway.
Can I find two-bedroom vacation rentals in Midtown?
Midtown has nine two-bedroom vacation rentals to select from. Go for a vacation home with all the privacy and comfort you need at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in Midtown?
Midtown has 22 vacation rentals with WiFi, so you'll be able to stay connected while traveling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Vrbo homes make it easy to get online.
How can I find vacation rentals with air conditioning in Midtown?
Midtown has 40 vacation rentals where you can kick back in air-conditioned comfort. To find a property on Vrbo that offers this perk, enter your travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Midtown?
We recommend checking with the Midtown vacation home you'd like on Vrbo as the minimum age differs. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Midtown for?
How long you can rent a vacation rental in Midtown varies according to the property. Simply enter your desired travel dates to see a list of options offering extended stays. With loads of amenities such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Midtown.
Does Vrbo offer discounts for vacation homes in Midtown?
Whether you're eyeing off one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some fabulous bargains and discounts on Vrbo. From short stays to extended getaways, we've got the perfect place for your next Midtown escape.

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