Old Town Key West holiday lettings

Why visit Old Town Key West

• Rich History: Discover the intriguing heritage of Old Town Key West through its historic architecture and landmarks.
• Vibrant Atmosphere: Stroll along lively streets filled with local shops, eateries, and cultural experiences.
• Stunning Beaches: Relax on beautiful beaches with soft sands and inviting waters, perfect for sunbathing.
• Local Excursions: Engage in various activities, from water sports to sightseeing tours, that highlight the area's charm.
• Charming Accommodations: Choose from a variety of quaint cottages and vacation rentals for a unique stay.

Popular types of accommodation around Old Town Key West

You've chosen Old Town Key West for your getaway, and now it's time to select the perfect accommodation. Discover the charm of historic Key West with our range of houses, condos, and quaint cottages. Whether you're seeking a relaxing retreat or a vibrant base to explore, our Old Town Key West rentals offer a variety of options to suit every traveller's needs. Start your adventure with our selection of top-notch Key West vacation rentals.

• Houses: The top choice for visitors to Old Town Key West, offering spacious and comfortable lodgings ideal for families or groups.
• Condos: A popular alternative, providing modern amenities and convenient locations for those seeking a bit of luxury.
• Cottages: Quaint and charming, these options offer a homely feel, perfect for a romantic getaway or a peaceful retreat.
• Apartments: A practical option for those wanting self-catering facilities in a vibrant neighbourhood.
• Villas: Elegant and spacious, villas provide an upscale experience with private pools and stunning views.**

Top attractions in and around Old Town Key West

Old Town Key West is an ideal destination for city-themed, family, or business holidays. Visitors can explore stunning beaches, vibrant streets, and iconic landmarks while immersing themselves in the local culture. Whether you're interested in sightseeing or simply enjoying the beach life, Old Town offers a delightful blend of experiences for all types of travellers. Don't miss the chance to visit this charming locale on your next adventure.

• Duval Street: A vibrant thoroughfare teeming with energy, Duval Street is the heart of Key West, featuring charming shops, lively bars, and delightful eateries. The street is perfect for strolling, soaking up the local atmosphere, and experiencing the island's nightlife.
• Southernmost Point: This iconic landmark marks the southernmost point in the continental USA, offering stunning ocean views and a colourful buoy for photo opportunities. It's a cultural symbol of Key West's laid-back lifestyle and maritime heritage.
• Ernest Hemingway Home and Museum: Explore the former residence of the renowned author, where you can admire the lush gardens and historic architecture. The museum offers insights into Hemingway's life, his literary works, and the unique charm of Key West.

Things to do recommended for couples

Seeking a romantic getaway in Old Town Key West? Explore the charming streets hand-in-hand, indulge in a sunset sail on the azure waters, or savour a candlelit dinner at a quaint bistro. Don't forget to visit the picturesque Mallory Square for stunning views and lively performances.

Things to do recommended for families

Families will love the MLK Community Pool & Community Center in Old Town Key West, where they can enjoy a refreshing swim in a family-friendly atmosphere. This outdoor facility offers a perfect spot for relaxation and fun after exploring the vibrant local area.

Things to do recommended for groups

Experience the vibrant atmosphere of Old Town Key West with a round of golf at the Key West Golf Club, only 2.5km away, and enjoy a captivating show at the Key West Burlesque Theater. Don’t forget to browse unique finds at The Kite House.

Booking with Vrbo is simple

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can be beneficial, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Old Town Key West

Old Town Key West offers a charming blend of history and tropical allure, perfect for family getaways, business retreats, or leisurely explorations. Wander the vibrant streets, where you can immerse yourself in the lively atmosphere, uncover local excursions, and indulge in adventure. With its picturesque architecture and rich heritage, Old Town Key West is a delightful destination for those seeking an unforgettable vacation experience.

• Key West: Nestled on a picturesque island, Key West is a vibrant city located 249m from Old Town. This tropical paradise is renowned for its family-friendly atmosphere and bustling city vibe. Visitors can indulge in various activities, from shopping at local boutiques to lounging on the beach. The local landmarks include stunning sandy shores and charming streets lined with colourful houses, making it a perfect spot for a leisurely stroll. Key West's diverse resorts cater to all types of travellers, ensuring a memorable experience for families and business visitors alike.
• Key West Historic District: Just 186m from Old Town, the Key West Historic District offers a delightful glimpse into the island's storied past. This neighbourhood is a blend of historical charm and modern conveniences, appealing to families and business travellers seeking a unique atmosphere. Visitors can explore quaint streets adorned with beautiful architecture, enjoy shopping at nearby areas, and relax on the nearby beaches. The Historic District is perfect for those looking to immerse themselves in the local culture while having access to various resorts and amenities.
• Downtown Key West: Located a mere 124m from Old Town, Downtown Key West is the energetic core of the island. This bustling neighbourhood is popular for its lively shopping areas, delightful cafés, and local resorts, making it ideal for families and business visitors alike. The nearby beaches provide a serene escape, while the vibrant streets are filled with shops and restaurants that showcase the island's unique flair. Downtown Key West is the perfect place to experience the island's charm while enjoying modern conveniences.

Best time to go to Old Town Key West

If you're planning a trip to Old Town Key West, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	71.1°F (21.7°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
February	72.1°F (22.3°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Average
March	73.4°F (23.0°C)	No Rain (Dry)	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.6°F (28.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Average	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
September	83.7°F (28.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
October	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Average	Average
December	73.9°F (23.3°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High

What do I need to keep in mind when booking a vacation around Old Town Key West

When travelling with a group, family, pets, or seeking extended stays, it's essential to refine your search according to your key priorities. Here are some helpful Vrbo booking tips for you.

• Traveling to Old Town Key West with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily refine your search for these and many other options on Vrbo.
• Traveling to Old Town Key West with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Old Town Key West: For many, a family holiday wouldn't be the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Old Town Key West: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your travel itinerary. You’ll discover your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.