Hotels in Midtown

Midtown Magic: Where Coastal Dreams Meet Urban Adventure

Discover the vibrant charm of Midtown, Key West, where island life meets eclectic culture. This lively neighborhood pulses with local art galleries, charming cafes, and colorful boutiques, all set against the backdrop of swaying palm trees and sunny skies. Explore nearby beaches perfect for family fun, or venture to the serene landscapes of the nearby national park for a taste of nature. With its laid-back atmosphere and friendly vibe, Midtown offers a delightful blend of relaxation and adventure, making it a must-visit destination for families, couples, and solo travelers alike. Experience the unique allure of this tropical paradise.

Discover great hotels in Midtown

Midtown Key West offers a variety of hotel accommodations, from cozy inns to modern hotels, with many providing free Wi-Fi. You’ll find an array of vacation rentals and house rentals, giving you options for a comfortable stay in this vibrant area. Here are some of the best hotels in Midtown that our travelers love:

1. Suite Dreams Inn by the BeachOpens in a new window: This adventurous 3.0-star Bed and Breakfast is perfect for those seeking a vibrant, LGBTQIA-friendly getaway. With an array of thrilling activities including windsurfing, fishing, parasailing, skydiving, and snorkeling available nearby, this hotel ensures an exhilarating stay. Guests appreciate the property's lively atmosphere and the chance to engage with nature, making it an ideal choice for leisure travelers who thrive on outdoor experiences and unique adventures.
2. Bayview houseOpens in a new window: At this stylish 3.5-star guesthouse, travelers can indulge in culinary delights with local dining options and unwind with entertainment features like streaming services on smart televisions. The ambiance creates a cozy yet contemporary vibe, making it an appealing destination for leisure travelers looking to relax in comfort. Guests frequently highlight the inviting environment and the ability to enjoy both entertainment and dining just steps away, perfect for those seeking a distinctive retreat.
3. Margaritaville Beach House Key WestOpens in a new window: This 3.5-star hotel offers a quintessential beach vacation experience with direct access to the sandy shores. The property is designed for travelers who prioritize relaxation and scenic beauty, allowing guests to soak up the sun and enjoy the tranquil ocean atmosphere. Positive sentiments revolve around the beach-centric lifestyle and the ease of access to stunning views, making it an exceptional choice for leisure travelers eager to unwind in a picturesque coastal setting.

Top locations to stay in Midtown

Staying near Duval Street, Southernmost Point, and Smathers Beach offers a vibrant experience in Midtown, Key West, Florida. Duval Street is perfect for nightlife and shopping, Southernmost Point provides iconic photo ops and historical sites, and Smathers Beach is ideal for relaxation and water activities. For first-time visitors, staying near Duval Street is best to fully immerse in the local culture.

1. Near Duval StreetOpens in a new window: Staying near Duval Street puts you right in the vibrant heart of Key West, where you can explore a lively mix of shops, galleries, and cultural attractions. Don’t miss the chance to visit the Ernest Hemingway Home and Museum and the Key West Lighthouse, both within walking distance. The area is also home to various cultural venues like the Waterfront Playhouse and the Red Barn Theater, providing plenty of entertainment options after sunset.
2. Near Southernmost PointOpens in a new window: Just a short stroll from the iconic Southernmost Point marker, this area offers a relaxed atmosphere with access to stunning views and historical sites like Fort Zachary Taylor Historic State Park. You'll find a great mix of local shopping and cultural experiences nearby, making it a perfect base for a laid-back getaway while still being close to the action.
3. Near Smathers BeachOpens in a new window: If you're looking for a spot to unwind by the water, staying near Smathers Beach is a fantastic choice. This beautiful beach offers a serene escape for sunbathing, swimming, and enjoying the scenic views of the ocean. Nearby, you'll find wellness options like the MLK Community Pool and Community Center, creating a perfect blend of relaxation and recreation.

Things to do near Midtown

Midtown is a vibrant hub where sun-soaked beaches meet lush parks, offering a perfect blend of relaxation and adventure. Enjoy thrilling activities like biking along scenic trails, diving into crystal-clear waters, and exploring family-friendly areas. With ample shopping and recreational spots, it’s a delightful destination for everyone!

• Duval StreetOpens in a new window – Stroll down Duval Street, the vibrant heart of Key West, where you can explore an eclectic mix of shops, galleries, and restaurants. This lively thoroughfare is perfect for an afternoon of wandering, grabbing a bite at a local café, or stopping by a quirky souvenir shop. As you walk, soak in the colorful architecture and the island vibe that makes this street a must-see.
• Southernmost PointOpens in a new window – Don't miss the Southernmost Point landmark, a symbolic buoy that marks the southern tip of the continental United States. Snap a photo with this iconic marker and enjoy the stunning ocean views that surround it. Take a moment to appreciate its significance while basking in the warm Florida sun, and consider taking a leisurely walk along the nearby waterfront for a refreshing breeze.
• Mallory SquareOpens in a new window – Head to Mallory Square, where the spirited atmosphere comes alive, especially during the sunset celebration. This modern square offers a fantastic spot to watch street performers, browse local artisan stalls, and enjoy live music. As the sun dips below the horizon, you'll be treated to a breathtaking view, making this the ideal place to unwind and experience the vibrant culture of Key West.

5 tips for savvy savings when booking a hotel in Midtown

1. Book for the cheapest times: The most affordable time to visit Midtown is from August to October, when hotel prices are typically lower. For a budget-friendly trip, a stay of at least 3 to 4 days is recommended to fully experience the area’s key landmarks, cultural sites, and historical attractions. During your visit, you can explore a variety of places such as museums, historic buildings, parks, and theaters. This timeframe may offer great value for money, allowing you to enjoy Midtown's rich history and vibrant culture without overspending.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Midtown, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you may find discounted rates on hotels as your travel date approaches. By enabling email alerts or push notifications, you could stay updated on flash sales and special promotions, ensuring you don't miss savings opportunities. Additionally, the Smart ShoppingOpens in a new window tool in the app allows you to compare hotel prices and amenities, helping you identify the best options. With these features, you’re more likely to be the first to know if prices drop or rooms become available for your last-minute getaway.
3. Be flexible with dates: Prices may fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay in a Midtown hotel. If you're seeking unique accommodations, boutique hotels often provide a more personalized experience and may offer better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll suggest more budget-friendly dates that could help you secure a better deal.
4. Consider your location: Staying near popular attractions or city centers can be convenient, but it usually tends to come with higher prices. For more budget-friendly options, consider hotels in neighborhoods that are a bit further away, allowing you to balance cost with easy access to the sights you want to visit. You might also look into independent hotels located further out, which can offer a more authentic experience while being more likely to be affordable.
5. Become a Member: Join for free and start booking your next stay in Midtown today! Enjoy savings on over 100,000 hotels around the globe with exclusive member rates. As a member, you can easily advance through membership tiers, unlocking exciting perks such as complimentary room upgrades (when available) and discounts on food and beverages at select VIP Access properties. Don't miss out on these fantastic benefits—sign up now!

Best time to go to Midtown

Midtown has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. March, June, and July are the peak travel months in Midtown, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by no to light rainfall. On the other hand, September to November tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.