Best Vacation Homes in Midtown
Private Pool
Oceanfront
Pool
Ocean View
- Oceanfront
Spa- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
Fireplace/Heating- Pool
Internet
Child Friendly
Laundry
Barbecue/Outdoor Cooking
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
Balcony/Terrace
10.0- Balcony/Terrace
Kitchen
Air Conditioner- Internet
10.0- Private Pool
- Oceanfront
Hot Tub- Fireplace/Heating
9.8- Private Pool
- Oceanfront
- Hot Tub
- Spa
Midtown Luxury Rentals
- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
9.8- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Private Pool
- Oceanfront
- Pool
- Ocean View
9.6- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Private Pool
- Oceanfront
- Pool
- Ocean View
Midtown Pet Friendly Vacation Rentals
- Balcony/Terrace
Pet Friendly- Kitchen
Parking
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
Midtown Large Vacation Homes
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
9.6- Child Friendly
Security/Safety
- Kitchen
- Air Conditioner
- Child Friendly
- Laundry
- Private Pool
- Pool
- Kitchen
- Air Conditioner
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
Why Choose Rent By Owner for your Midtown Vacation Rental Homes?
What makes our Vacation Rentals special?
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 2116+ Rentals in Old TownNew 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 87+ Rentals in New TownThe 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 102+ Rentals in The MeadowsWhite 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 4531+ Rentals in White St. GalleryWhite 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 4527+ Rentals in White Street Gallery DistrictBest 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
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.
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.
Off-Season Highlights
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.
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.
Weekly Weather Forecast for Midtown
How to Book Your Midtown Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Midtown
Common Vacation Rentals Amenities
What amenities can you expect?
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.
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.
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:
- Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
- *BELLE OF THE BEACH @ CASA EAST* Beach House + LAST KEY SERVICES…
- *LARGE PRIVATE HEATED POOL and PATIO*1/3 Mile from Beach
- BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
- Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Gorgeous beach bungalow just steps from the beach!
- SOUTHERNMOST SWIM AND SOCIAL CLUB
- *MIDTOWN MOSAIC @ MIDTOWN* Modern Private Home & Pool + LAST KEY SERVICES…
- Atlantis House Suites
- Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
2. How many vacation rentals have private pools in Midtown?
There are 22 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 2026 is over 89 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?
6. How do I confirm the availability of a specific property?
7. Are there any additional fees I should be aware of before booking?
8. What amenities are included with vacation rentals in the region?
9. What is the check-in and check-out process for these properties?
Midtown Top Rated Vacation Rentals
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
9.6- Hot Tub
- Spa
- Fireplace/Heating
- Pool
9.6- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
9.6- Private Pool
- Oceanfront
- Pool
- Ocean View
8.0- Pool
- Balcony/Terrace
- Kitchen
- Parking
8.0- Private Pool
- Oceanfront
- Pool
- Ocean View
- Private Pool
- Pool
- Pet Friendly
- Kitchen
