Find hotels near Jackson Square, Key West from $164

Find great hotels near Jackson Square

Discover a variety of hotel accommodations in Jackson Square, Key West, Florida, where you can enjoy a mix of resort-style stays and charming bed & breakfasts. Whether you're seeking adventure, a historic-themed getaway, or a romantic vacation experience, this vibrant area offers top-rated hotels with excellent reviews. Explore your options and find your favorite hotel near Jackson Square for an unforgettable trip.

• La Concha Key West, Autograph Collection: Located a mere 0.1 mile from Jackson Square, La Concha Key West, Autograph Collection offers a sophisticated blend of family-friendly and business-oriented accommodations. This 4-star hotel is especially welcoming to LGBTQIA travelers, providing an inclusive environment that is recognized by LGBTQI travel guides. Guests can enjoy a range of amenities tailored for families, including complimentary cribs and window guards to ensure children's safety. With a central location, it serves as a perfect base for exploring the vibrant attractions of Key West.
• Opal Key Resort & Marina, Key West: Situated 0.3 mile from Jackson Square, Opal Key Resort & Marina, Key West is a 4-star haven for adventure seekers and pet lovers alike. The resort boasts a variety of thrilling activities, such as parasailing, fishing, and snorkeling, all available either onsite or nearby. The pet-friendly policy allows dogs with certain restrictions, ensuring that your furry friends can join in the fun. With its prime location and extensive recreational options, this resort is perfect for those looking to dive into the thrilling outdoor experiences that Key West has to offer.
• Heron House - Adult Only: Just 0.2 mile from Jackson Square, Heron House - Adult Only is a charming 3.5-star Bed & Breakfast that caters exclusively to adults seeking an adventurous and LGBTQIA-friendly escape. The property is affiliated with LGBTQI travel guides and offers a range of water sports and outdoor activities, including snorkeling and sailing, all within close proximity. With its welcoming atmosphere and focus on unique experiences, guests can enjoy a serene yet adventurous vacation amid the vibrant backdrop of Key West.

Where to stay near Jackson Square

Jackson Square in Key West offers an exciting blend of tropical adventure and rich history. Visitors can explore nearby parks and enjoy the vibrant atmosphere of this iconic tourist thoroughfare. With its convenient location, you'll find plenty of awesome stays and easy access to local attractions. Immerse yourself in the unique vibes of the area and discover why Jackson Square is a must-visit destination for travelers seeking both relaxation and exploration.

• Key West: Nestled at the southernmost point of the continental United States, Key West is a vibrant island city known for its laid-back atmosphere and stunning sunsets. Jackson Square serves as a central hub for visitors to explore the charming streets lined with colorful conch houses, eclectic shops, and lively bars. This destination is ideal for families, business travelers, and those seeking a city-themed experience. Highlights include beautiful beaches, family-friendly activities, and a variety of shopping options. Peak travel months like January, March, and September promise a bustling yet welcoming environment.
• Old Town Key West: Old Town Key West, where Jackson Square is located, offers a unique blend of history and culture. This neighborhood features narrow streets filled with historic architecture, art galleries, and quaint cafes, making it perfect for those looking to soak up the local vibe. Visitors can enjoy a mix of city-themed attractions alongside family-friendly activities. The area boasts easy access to beaches and shopping venues, ensuring a well-rounded experience. With peak visitor numbers in March and the summer months, Old Town Key West is lively and full of charm.
• Key West Historic District: Just 0.3 miles from Jackson Square, the Key West Historic District is a treasure trove of history and culture. This neighborhood is characterized by its preserved buildings, rich maritime history, and lively street life. Travelers can enjoy various shopping areas, resorts, and nearby beaches, making it a great spot for families and business visitors alike. The area's peak seasons mirror those of the surrounding neighborhoods, making it a bustling destination filled with engaging activities and attractions.

Things to do near Jackson Square

Jackson Square in Key West offers a vibrant mix of activities and attractions, including stunning sunsets, lively festivals, and biking adventures. Visitors can enjoy a dynamic nightlife scene with jazz clubs, explore nearby museums, and indulge in shopping at local boutiques. With its unique blend of culture and entertainment, Jackson Square promises an unforgettable experience for every tourist.

Shopping

For a unique shopping experience in Jackson Square, visit We Cycle Key West, just 0.1 mile away, and The Kite House, located 0.4 miles away. If you're up for a drive, the Big Pine Key Flea Market, 29 miles away, offers a vibrant atmosphere with diverse vendors.

Recreation

Key West Golf Club, located 4 miles from Jackson Square, offers a beautiful outdoor space perfect for golf enthusiasts. Enjoy the lush greens and invigorating sea breezes. For a family-friendly option, the MLK Community Pool & Community Center, just 0.5 miles away, features a refreshing pool ideal for relaxation and recreation.

Adventure

Jackson Square is a vibrant hub filled with street performers, local artists, and historic architecture. Explore the nearby French Market for unique souvenirs, or take a guided ghost tour to uncover the spooky tales of the past. Enjoy live music in the evenings for a lively atmosphere.

Nightlife

Experience the vibrant nightlife in Jackson Square with a visit to the Waterfront Playhouse, just 0.4 miles away, for captivating performances. Alternatively, enjoy the charm of the Red Barn Theater, located 0.2 miles away, or indulge in the allure of the Key West Burlesque Theater, 0.7 miles from the square.

Booking tips and Expedia advantages for Jackson Square

To save money on your trip to Jackson Square, plan your visit between August and October when hotel prices are lower. Book your stay about a month in advance, ideally on a Tuesday for the best rates. Use Expedia to find last-minute deals, sort prices from lowest to highest, and consider packaging your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can also unlock exclusive discounts and earn OneKeyCash for future bookings. Lastly, explore free activities in the area to keep your costs down while enjoying your vacation.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Jackson Square are August to October, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher.
• The best time to book a hotel: Book your hotel around Jackson Square about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Jackson Square is Tuesday. The most expensive day to stay around Jackson Square is Friday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, preferred location, and desired hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay near Jackson Square with your flights and activities.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Best time to go to Jackson Square

The best time to visit Jackson Square can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Jackson Square falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Jackson Square falls in January, visitor numbers are average and weather is mostly sunny with no rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	71.1°F (21.7°C)	No Rain	Mostly Sunny	Average	Average
February	72.1°F (22.3°C)	No Rain	Mostly Sunny	Average	Slightly High
March	73.4°F (23.0°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
April	76.8°F (24.9°C)	No Rain	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	Slightly High	Average
July	84.0°F (28.9°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	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	Slightly Low
November	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	73.9°F (23.3°C)	No Rain	Mostly Sunny	Average	Average