Discover Your Perfect Midtown Vacation Homes

Midtown Luxury Rentals

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Midtown Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Midtown Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Midtown Vacation Rentals

Where are the best neighborhoods to stay in Midtown?

Exploring Midtown in Key West, Florida offers you a unique opportunity to experience the vibrant local culture while enjoying convenient access to the island’s renowned attractions. The neighborhood’s laid-back atmosphere and charming streets make it an ideal choice for those seeking authentic Florida living. Whether you're looking to relax in a stylish vacation rental or explore nearby hotspots, staying in Midtown provides a comfortable and accessible base for your Key West adventure. Booking through trusted vacation rentals ensures a seamless experience, allowing you to focus on making lasting memories in this picturesque coastal setting.

Old Town

This historic neighborhood offers charming streets and cultural charm, making it an ideal area to find unique vacation rentals near the heart of Key West. Staying here puts you close to the region's most iconic sights and vibrant local life.

View 2836+ Rentals in Old Town

New Town

Known for its modern developments and convenient access to the region’s scenic waterways, New Town is a great choice for travelers seeking comfortable vacation rentals close to key attractions and waterfront activities.

View 126+ Rentals in New Town

The Meadows

Surrounding lush parks and peaceful streets, The Meadows provides a tranquil setting for your stay, with a variety of vacation rentals that offer relaxation while still being near the lively downtown core.

View 116+ Rentals in The Meadows

White St. Gallery

This artsy neighborhood boasts colorful galleries and creative vibes, making it a perfect spot to find eclectic vacation rentals immersed in the local artistic scene of the region.

View 29+ Rentals in White St. Gallery

White Street Gallery District

Centered around vibrant art venues and boutique shops, this district invites you to enjoy stylish vacation rentals nestled within a thriving cultural atmosphere, ideal for exploring the artistic spirit of the area.

View 29+ Rentals in White Street Gallery District

Best Times to Visit Midtown

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this destination allows you to enjoy pleasant weather and avoid peak crowds, ensuring a more relaxing experience when booking your vacation rentals in the area.

Peak Season Highlights

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Winter (December to April)

During the winter months, you can enjoy the warm climate and lively events in the area, making it a popular time for visitors seeking sunshine and outdoor activities.

Average Temperature Daytime: 75°F - 80°F - Nighttime: 65°F - 70°F
summer
Summer (June to August)

This bustling season attracts travelers looking for vibrant nightlife and water-based adventures, ensuring your stay coincides with the area's liveliest period.

Average Temperature Daytime: 85°F - 90°F - Nighttime: 78°F - 82°F

Off-Season Highlights

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Late Fall (October to November)

As the crowds thin out, you'll find more relaxed atmospheres and easier access to local attractions, ideal for a peaceful getaway.

Average Temperature Daytime: 76°F - 80°F - Nighttime: 68°F - 72°F
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Early Spring (March to April)

Just before the peak season begins, this is a serene time to enjoy the region's natural beauty with fewer visitors around.

Average Temperature Daytime: 74°F - 78°F - Nighttime: 64°F - 67°F

Weekly Weather Forecast for Midtown

How to Book Your Midtown Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Midtown

More Top-Rated Vacation Rentals in Midtown Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for relaxing meals under the sun or stars.
  • Take advantage of private pools or hot tubs to unwind after exploring the local attractions.
  • Benefit from lush landscaped gardens or courtyards that add tropical charm to your stay.
  • Relax on spacious decks or patios equipped with lounge furniture for soaking up the sunshine.
  • Utilize outdoor grilling stations to prepare delicious meals in a scenic setting.
  • Experience shaded verandas or porches ideal for reading or enjoying a cool breeze.
  • Make the most of nearby outdoor recreational amenities like bike paths or walking trails for active adventures.

Top Attractions Around Midtown

What attractions are nearby?

Within this vibrant area, you'll find a variety of engaging activities nearby, including exploring local art galleries, enjoying scenic waterfront strolls, and experiencing the lively dining scene that captures the essence of this destination.

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Family Activities

  • Key West Aquarium: Discover fascinating marine life at this family-friendly attraction, offering interactive exhibits and educational displays right in the heart of the area.
  • Old Town Trolley Tour: Hop aboard a guided trolley tour to explore the region’s historic sites and vibrant neighborhoods, making it an engaging experience for all ages here.
  • Fort Zachary Taylor Historic State Park: Enjoy a day at the beach with swimming, picnicking, and exploring Civil War-era fortifications within this scenic park on the island.
  • The Pharmacy Museum: Step into the past with this unique museum housed in a former pharmacy, offering hands-on demonstrations and engaging stories suited for family exploration here.
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Adult Activities

  • Sunset Cruise Tours: Embark on a scenic evening cruise to witness the breathtaking sunsets that define this vibrant destination.
  • Historic Old Town Exploration: Wander through charming streets filled with unique shops, galleries, and architecture that showcase the area's rich history.
  • Art Gallery Hopping: Discover contemporary and local art at renowned galleries nestled within the region's lively arts scene.
  • Fine Dining Experiences: Indulge in exquisite culinary offerings at highly-rated restaurants that highlight the area's fresh seafood and local flavors.

Midtown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take the time to enjoy the region’s renowned culinary scene by visiting local restaurants and trying fresh seafood dishes unique to this destination.
  • Visit Nearby Beaches: Maximize your stay by relaxing at the nearby beaches, soaking up the sun and enjoying the tranquil ocean views that define this area.
  • Experience the Nightlife: Make the most of your evenings by exploring vibrant local bars and entertainment venues that highlight the region's lively atmosphere.
  • Discover Unique Attractions: Plan visits to the area's distinctive attractions that showcase its unique charm and cultural heritage, enriching your overall experience here.

Transportation Options

  • Rental Car Services: Explore the area at your own pace with rental cars conveniently available, offering flexible transportation from your vacation rental in Midtown, Key West.
  • Local Taxis and Rideshares: Easily access taxis and rideshare options that provide quick, reliable trips around this vibrant destination and its charming neighborhoods.
  • Bicycle Rentals: Enjoy a scenic ride through the region's picturesque streets by renting a bicycle, perfect for exploring nearby attractions from your vacation rental.
  • Public Transit Options: Benefit from local bus services designed to connect you with key points of interest while providing an economical way to get around here.

Local Customs Options

  • Conch Shell Blowing: Locals and visitors alike partake in the tradition of shell blowing, which is a cherished symbol of the area's maritime heritage and often celebrated during community events.
  • Sunset Celebrations: Watching the sunset at Mallory Square with street performers and local artisans demonstrates a beloved custom that captures the vibrant spirit of this island destination.
  • Gulf Coast Seafood Dining: Enjoying fresh seafood prepared in local styles reflects the region's culinary customs rooted in its coastal environment and fishing traditions.
  • Festivals and Parades: Participating in lively festivals and colorful parades showcases the area's rich cultural history and the community’s welcoming attitude toward visitors.

Frequently Asked Questions About Midtown?

1. What are the top vacation rentals in Midtown?

There are a lot of options in Midtown. If you plan on staying in the Midtown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Midtown:

2. How many vacation rentals have private pools in Midtown?

There are 19 vacation rentals with private pools near Midtown. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Midtown are best for families?

If you are looking for a family-friendly vacation home in Midtown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Midtown:

4. How many Rentbyowner vacation rentals are available in Midtown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 88 in the Midtown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Midtown. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property listing. Please review the specific cancellation terms outlined in the rental listing or contact the owner directly to understand any fees or restrictions.

6. How do I confirm the availability of a specific property?

Availability is updated regularly on the booking platform. To confirm, you should check the calendar provided in the listing and consider reaching out to the property owner for real-time confirmation.

7. Are there any additional fees I should be aware of before booking?

Additional fees such as cleaning, service charges, or taxes are typically detailed in the listing. Be sure to read the full description or contact the owner for clarification on any extra costs involved.

8. What amenities are included with vacation rentals in the region?

Property amenities vary but often include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. For a complete list, review the amenities section of the listing or contact the host directly.

9. What is the check-in and check-out process for these properties?

Check-in and check-out procedures are specified in each listing and may vary by property. It’s recommended to communicate directly with the owner for detailed instructions to ensure a smooth arrival and departure.

Midtown Top Rated Vacation Rentals

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