Hotels in Old Town Key West

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Where to stay in Old Town Key West?

3 outdoor pools, open 7:00 AM to 10:00 PM, pool loungers
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1073)
The price is ฿7,616
฿10,165 total
includes taxes & fees
15 Dec - 16 Dec
Winslow's Bungalows - Key West Historic Inns
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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When is the best time to visit Old Town Key West?

Our prices for hotels in Old Town Key West are cheapest in September
Price trends for hotels in Old Town Key West
Pricing is based on two traveller single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Key West
December
High crowds
High 24°C / low 22°C. Sunny most days.
View properties in December
24°
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December, High crowds, average high temperature 24 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
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23°
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January, Low crowds, average high temperature 23 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
23°
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February, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
24°
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March, High crowds, average high temperature 24 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
22°
26°
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April, Moderate crowds, average high temperature 26 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
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27°
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May, High crowds, average high temperature 27 degrees Celsius, average low temperature 26 degrees Celsius. Sunny most days.
26°
29°
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June, Moderate crowds, average high temperature 29 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
27°
29°
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July, High crowds, average high temperature 29 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
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30°
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August, Moderate crowds, average high temperature 30 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
28°
29°
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September, Low crowds, average high temperature 29 degrees Celsius, average low temperature 28 degrees Celsius. Sunny most days.
28°
28°
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October, Low crowds, average high temperature 28 degrees Celsius, average low temperature 27 degrees Celsius. Sunny most days.
27°
26°
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November, Low crowds, average high temperature 26 degrees Celsius, average low temperature 24 degrees Celsius. Sunny most days.
24°
Monthly weather averages (˚C)

Top landmarks in Old Town Key West

Southernmost Point which includes signage and general coastal views as well as children

Southernmost Point

4.3/5 (8,345 reviews)
If you're planning a bit of sightseeing, head to Southernmost Point – just one of the monuments in Old Town Key West. Why not take a stroll along the beaches and watch the sunset while you're here?
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Exploring the historic Ernest Hemingway Home and Museum in Key West, Florida, a glimpse into the writer's life and work in a charming tropical setting

Ernest Hemingway Home and Museum

4.5/5 (4,055 reviews)
Ernest Hemingway Home and Museum is just one of the attractions in Old Town Key West, Key West so you might want to stop by during your trip. Why not take a stroll along the beaches and watch the sunset while you're here? If you want to experience more of the culture Key West has to offer, head to Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Key West Butterfly and Nature Conservatory.
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Check out reviews of Old Town Key West hotels guests love

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"The staff was welcoming, friendly and helpful. The resort itself was well kept."
Erin 3-night trip
Posted 17 hours ago
The Cabana Inn Key West - Adults Only

Frequently asked questions

Is Old Town Key West expensive to stay in?
You can find great hotels from ฿5,346 in Old Town Key West to suit a range of budgets. If you're looking for an affordable stay in Old Town Key West, Southwinds Motel is a great low-cost option. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Old Town Key West hotels?
Discover great deals on hotels in Old Town Key West with Hotels.com. Sign up for free to unlock member only prices and start earning rewards. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Old Town Key West hotels.
How can I find discounted rates and deals for Old Town Key West hotels?
Unlocking discounted rates at hotels in Old Town Key West couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Old Town Key West hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Old Town Key West hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
What are the top-rated luxury hotels in Old Town Key West?
One of the best-rated luxury hotels in Old Town Key West is The Porch on Frances Inn. The Porch on Frances Inn has a high guest rating amongst our travellers and has wedding services, a hair salon and in-room champagne service.
What are some of the best Old Town Key West beach hotels?
The Reach Key West, Curio Collection by Hilton, Southernmost Beach Resort and Guesthouses, and Casa Marina Key West, Curio Collection by Hilton are some of the best Old Town Key West beach hotels. The Reach Key West, Curio Collection by Hilton has a high average guest score of 8.4 out of 10, and offers guests a private beach and an outdoor pool. Southernmost Beach Resort and Guesthouses is a popular place to stay for easy beach access. Stay here and enjoy a beachfront setting and 3 outdoor pools. Or check out Casa Marina Key West, Curio Collection by Hilton, a top hotel with a private beach and 2 outdoor pools.
What are some of the best Old Town Key West hotels for couples?
Some of the best Old Town Key West hotels for couples include The Porch on Frances Inn and The Gardens Hotel. The Porch on Frances Inn is a popular inn with champagne service in each accommodation. Travellers also love The Gardens Hotel where you can enjoy a garden-view restaurant, as well as champagne service in each accommodation. Find more romantic Old Town Key West hotels by using the "Traveller experience" filter in your search and selecting "Adults only" or "Romantic".
What are some of the best family hotels in Old Town Key West?
If you're holidaying with your family, Santa Maria Suites and The Reach Key West, Curio Collection by Hilton are some of the best family hotels in Old Town Key West. Santa Maria Suites has a great average guest score of 9.6 out of 10 and amenities like 2 outdoor pools and in-room cots. Kids are welcome at The Reach Key West, Curio Collection by Hilton, too. Travellers leave glowing reviews of this resort, which has a private beach, an outdoor pool, in-room cots, and more. To explore more family hotels in Old Town Key West, use the "Family friendly" filter in your search on Hotels.com.
What are some of the best Old Town Key West hotels with a pool?
Book a Old Town Key West hotel with a pool for some added relaxation or exercise on your trip. For more Old Town Key West hotels with a pool, use the "Amenities" filter in your search and select "Pool" on Hotels.com.
What are some of the top Old Town Key West hotels with free parking?
If you're travelling by car, make your life easier by booking a Old Town Key West hotel with free parking. Our travellers like:
Is it worth staying in Old Town Key West?
You're spoilt for choice with 1,335 hotels in the area so it's easy to find your perfect somewhere. Basing yourself in Old Town Key West makes it easy to explore Key West, including the areas of Key West Historic District and New Town.
What are some great hotels in Old Town Key West with balconies?
There are some top hotels in Old Town Key West that offer rooms with a balcony. Check out The Porch on Frances Inn which has a high guest score of 9.6 out of 10, and furnished patios in some rooms. Another popular choice is The Gardens Hotel, which offers a furnished balcony/patio in every room, and has a great guest score of 9.8.
Find out more about Old Town Key West

Discover the Enchantment of Old Town Key West: Where Vibrant Streets Meet Serene Shores

Old Town Key West is a vibrant tapestry of history, charm, and tropical allure. Nestled in the heart of Key West, this historic district boasts colourful conch houses, lively streets, and a rich maritime heritage. Stroll along the iconic Duval Street, where boutiques, galleries, and eclectic bars invite exploration. Don’t miss the stunning sunsets at Mallory Square, or a visit to the famous Key West Lighthouse. With its laid-back atmosphere, delicious seafood, and cultural treasures, Old Town is not just a destination but an experience, perfect for families, couples, and those seeking a slice of paradise.

Things to do near Old Town Key West

Old Town Key West invites travellers to explore its charming streets, vibrant markets, and relaxing beaches. Enjoy leisurely strolls through historic areas, indulge in local shopping, or unwind at family-friendly parks. With opportunities for boating, diving, and golfing, this destination offers a delightful mix of relaxation and recreation.

  • Simonton BeachOpens in a new window – Relax and soak up the sun at Simonton Beach, a charming spot ideal for families. With its soft sand and gentle waves, it’s perfect for a day of swimming or building sandcastles. Take a leisurely stroll along the shoreline or enjoy a picnic with your loved ones. The beach is also conveniently located near a modern square, making it easy to explore nearby shops and eateries after a day of fun in the sun. Whether you're looking to unwind with a good book or engage in some beach games, Simonton Beach offers a welcoming atmosphere for everyone.

4 tips for savvy savings when booking a hotel in Old Town Key West

  1. Book for the cheapest times: The most affordable time to visit Old Town Key West is between August and October, when hotel prices are typically lower. For a thorough exploration of the area's key landmarks, cultural attractions, and historical sites, a stay of at least 3 to 4 days is recommended. During this time, visitors can enjoy attractions such as historic forts, museums, art galleries, and charming streets filled with unique shops. This budget-friendly approach allows travellers to experience the rich history and culture of Old Town Key West without breaking the bank.
  2. Look for last-minute deals on Hotels.com: To uncover last-minute deals to Old Town Key West, visit the DealsOpens in a new window or Last-Minute Deals sections on Hotels.com, where you may discover discounted hotel rates as your travel date approaches. Consider enabling email alerts or push notifications from Hotels.com to stay updated on flash sales and special promotions, helping you seize opportunities to save. Additionally, Smart Shopping is a comparison tool available via the app that allows you to compare hotel prices and amenities, ensuring you’re among the first to know if prices drop or rooms become available for your last-minute escape.
  3. Be flexible with dates: Prices may fluctuate due to factors such as 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 at a hotel in Old Town Key West. For those in search of distinctive accommodations, boutique hotels can provide a more personalised experience and potentially 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 appears to be on the higher side, we’ll suggest alternative dates that may offer more affordable options, helping you to secure a better deal.
  4. Consider your location: Choosing accommodation near key attractions or city centres may offer convenience but often tends to come with higher costs. For more affordable options, consider hotels situated in less central areas or neighbourhoods, striking a balance between price and ease of access to your planned destinations. You might also look into independent hotels located further out, which are more likely to provide a genuine and budget-friendly experience.

Best time to go to Old Town Key West

Old Town Key West 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 Old Town Key West, 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.

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