Discover the Best Old Town Key West Hotels for Your Perfect Vacation
Old Town Key West Hotels

If you’re planning a visit to Key West, staying in Old Town Key West hotels will put you in the heart of this beautiful island. Old Town Key West is the most popular part of the city, known for its historic charm, beautiful streets, and fun activities. Whether you’re looking for a luxury stay or a cozy guesthouse, there’s something for everyone in this part of the island.
In Old Town, you’ll find a mix of historic homes and modern hotels, all offering unique experiences. From stylish boutique inns to charming bed-and-breakfasts, each hotel has its own personality. So, if you want to enjoy the best of Key West, staying in Old Town is the perfect choice.
Table of Contents
Why Choose Old Town Key West Hotels for Your Stay?
Old Town Key West hotels offer a truly unique experience for anyone visiting the island. When you stay in Old Town, you are in the heart of Key West, with easy access to everything this charming destination has to offer. Whether you’re here for a romantic getaway, a family vacation, or a relaxing solo trip, Old Town is where you want to be.
The area is filled with colorful houses, historic streets, and attractions that make Key West famous. By staying in Old Town, you’ll be just a short walk from the beach, local shops, and delicious restaurants. Plus, you can explore museums, art galleries, and the lively nightlife that Key West is known for.
Old Town Key West hotels also offer a variety of choices to fit your budget and style. From cozy bed-and-breakfasts to luxury resorts, you can find a place that suits your needs perfectly. The charm of Old Town adds a special touch to your stay, making it more memorable.
Top 5 Old Town Key West Hotels You Need to Know About

There are many great places to stay in Old Town Key West, and here are five of the best. Each of these hotels brings something unique, making your vacation unforgettable. Whether you’re looking for a luxury escape or a laid-back experience, you’ll find what you’re looking for.
- Winslow’s Bungalows – A luxurious hotel with beautiful rooms and three outdoor pools.
- The Mermaid and The Alligator – A cozy B&B offering tropical rooms and a peaceful atmosphere.
- The Conch House Heritage Inn – A charming inn with a large pool and delicious breakfasts.
- Ella’s Cottage – A boutique guesthouse surrounded by lush gardens and peaceful rooms.
- The Paradise Inn – A tranquil adults-only inn with an outdoor pool and hot tub.
Each of these Old Town Key West hotels offers a different experience, so you can choose the one that fits your vacation style the best.
What Makes Old Town Key West Hotels So Special?
Old Town Key West hotels are not just places to sleep—they offer a full experience that connects you to the island’s history and culture. Staying here gives you the chance to explore Key West’s beautiful architecture and scenic streets. Many hotels are housed in restored historic buildings, allowing you to enjoy the charm of the past while still having modern amenities.
The service in Old Town hotels is top-notch, with staff members always ready to help you make the most of your visit. Whether it’s booking a sunset sail or offering recommendations for the best local restaurants, they ensure you have everything you need for a perfect stay. The personal touch these hotels offer makes a big difference.
The Best Old Town Key West Hotels for a Romantic Getaway
If you’re planning a romantic trip, Old Town Key West hotels are perfect for couples. The charming streets, scenic views, and laid-back atmosphere make it an ideal place for a getaway with your loved one. Imagine spending the day exploring the island and then retreating to a peaceful, cozy hotel to unwind.
Here are some romantic options for your stay:
- The Paradise Inn – An adults-only B&B with a relaxing hot tub and quiet ambiance.
- The Mermaid and The Alligator – A quiet B&B with tropical decor and a private pool.
- Winslow’s Bungalows – Perfect for couples looking for luxury and comfort, with private patios and outdoor pools.
These hotels offer peaceful settings, beautiful views, and excellent service that will make your romantic trip even more special.
Family-Friendly Old Town Key West Hotels You Will Love
Old Town Key West is a great destination for families, and there are many family-friendly hotels to choose from. Whether you’re traveling with young children or teens, the hotels in Old Town offer a relaxing and fun place to stay.
- Ella’s Cottage – A boutique guesthouse with spacious rooms and a beautiful garden for kids to explore.
- The Conch House Heritage Inn – With a large pool and family-sized rooms, it’s a great place for families to relax together.
Many Old Town hotels are close to local parks, beaches, and attractions, so your family will never run out of things to do.
Relax and Unwind: The Best Old Town Key West Hotels with Pools

Many visitors to Key West want to relax and cool off in a nice pool, and the best Old Town hotels offer just that. Whether you prefer lounging by the pool or swimming to stay active, the hotels in Old Town have excellent pool options.
- Winslow’s Bungalows – With three outdoor pools, this hotel offers plenty of space to relax.
- The Paradise Inn – The pool is surrounded by lush gardens, making it a peaceful retreat.
- The Mermaid and The Alligator – A quiet pool area perfect for unwinding after a day of sightseeing.
Having a pool at your hotel is a great way to enjoy the sunshine and take a break from your daily adventures in Key West.
Conclusion
Staying in Old Town Key West hotels is a great way to experience the charm of the island. With so many different types of hotels, you’re sure to find one that fits your needs perfectly. Whether you want to relax by the pool, explore the historic streets, or enjoy a romantic getaway, Old Town has it all. The friendly atmosphere and beautiful surroundings make it an unforgettable place to stay.
Whether you’re visiting for a weekend or a week-long vacation, Old Town Key West hotels offer something special for everyone. Don’t miss out on the chance to stay in the heart of Key West and enjoy everything this amazing place has to offer. It’s the perfect spot to create memories and have a great time with family, friends, or a loved one.
FAQs
Q: What is the best time to visit Old Town Key West?
A: The best time to visit is from December to April when the weather is sunny and warm.
Q: Are Old Town Key West hotels family-friendly?
A: Yes, many hotels in Old Town are great for families, offering pools and spacious rooms.
Q: Can I find affordable hotels in Old Town Key West?
A: Yes, there are affordable options in Old Town, ranging from cozy guesthouses to budget-friendly B&Bs.
Q: Are Old Town Key West hotels near the beach?
A: Yes, many hotels in Old Town are just a short walk or drive from the beach.
Q: Do Old Town Key West hotels offer breakfast?
A: Yes, many hotels offer complimentary breakfast, and some even serve it by the pool.