Find hotels near Jackson Square, Key West from AED 690

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Our top choices for Jackson Square hotels

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Downtown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1001)
"Very nice & peaceful with a wonderful staff. Our second time staying here"
United States
Sandra
The price is AED 735
AED 827 total
includes taxes & fees
18 Dec - 19 Dec
Almond Tree Inn Hotel - Adults Only

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1001)
"Perfect place to stay. "
United States
Paulette
The price is AED 2,016
AED 2,475 total
includes taxes & fees
21 Dec - 22 Dec
The Marquesa Hotel

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 0.7 km from Jackson Square
9.8 out of 10, Exceptional, (144)
"Fantastic location "
United States
ANDREW
The price is AED 706
AED 794 total
includes taxes & fees
18 Dec - 19 Dec
The Conch House Heritage Inn

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1002)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is AED 710
AED 798 total
includes taxes & fees
18 Dec - 19 Dec
Orchid Key Inn - Adults Only

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (363)
"The place was excellent and the service amazing "
United States
Janae
The price is AED 628
AED 799 total
includes taxes & fees
17 Dec - 18 Dec
Tropical Inn

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.2 km from Jackson Square
9.4 out of 10, Exceptional, (922)
"Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat."
United States
Robert
The price is AED 932
AED 1,049 total
includes taxes & fees
8 Jan - 9 January 2026
L'Habitation Guest House

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (995)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is AED 1,065
AED 1,198 total
includes taxes & fees
21 Dec - 22 Dec
Weatherstation Inn

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1010)
"I loved this place the location was absolutely perfect "
United States
Frank
The price is AED 544
AED 690 total
includes taxes & fees
18 Dec - 19 Dec
Duval House

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (408)
"The cottage was perfect, centrally located and a wonderful place to stay!"
United States
Claudia
The price is AED 840
AED 1,131 total
includes taxes & fees
17 Dec - 18 Dec
Ella's Cottages - Key West Historic Inns

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1024)
"We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast."
United States
Susanne
The price is AED 493
AED 802 total
includes taxes & fees
18 Dec - 19 Dec
Silver Palms Inn

Southernmost House

Southernmost House
4.0 star property
Uptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1002)
"Great place to stay. Staff was very friendly"
United States
Jacob
The price is AED 988
AED 1,453 total
includes taxes & fees
17 Dec - 18 Dec
Southernmost House

The Key West Hotel

The Key West Hotel
2.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (514)
"location was great nice bar party vibe"
United States
Robert Howard
The price is AED 813
AED 1,117 total
includes taxes & fees
17 Dec - 18 Dec
The Key West Hotel

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Downtown Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1004)
"Cozy place right near everything "
United States
Joseph
Paradise Inn Key West - Adults Only

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1006)
"Great stay."
United States
Sarit
The price is AED 1,539
AED 2,016 total
includes taxes & fees
17 Dec - 18 Dec
Ocean Key Resort - A Noble House Resort

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (857)
"Room was clean, staff were awesome."
United States
Bridget
The price is AED 915
AED 1,215 total
includes taxes & fees
17 Dec - 18 Dec
Ridley House - Key West Historic Inns

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1008)
"Fantastic staff, great breakfast"
United States
Kelly
The price is AED 790
AED 1,120 total
includes taxes & fees
17 Dec - 18 Dec
The Marker Key West Harbor Resort

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West, 0.8 km from Jackson Square
9.2 out of 10, Wonderful, (1075)
"Beautiful property, nice clean bungalows and great staff!"
United States
Robert
The price is AED 840
AED 1,131 total
includes taxes & fees
17 Dec - 18 Dec
Winslow's Bungalows - Key West Historic Inns

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.0 out of 10, Wonderful, (1137)
"Loved the setup of the hotel and great location! "
United States
Rachel
The price is AED 1,202
AED 1,496 total
includes taxes & fees
4 Jan - 5 January 2026
Heron House - Adult Only

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.0 out of 10, Wonderful, (1010)
"Staff was courteous and the location is perfect for a weekend in Key West."
United States
TIMOTHY
The price is AED 896
AED 1,248 total
includes taxes & fees
17 Dec - 18 Dec
Hyatt Centric Key West Resort and Spa

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
3.5 star property
Bahama Village, 0.5 km from Jackson Square
9.0 out of 10, Wonderful, (847)
"Great location. Near great food and entertainment."
United States
David
The price is AED 759
AED 1,040 total
includes taxes & fees
17 Dec - 18 Dec
Lighthouse Hotel - 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.

Top Jackson Square Hotel Reviews

Hotels near other Jackson Square attractions

Find out more about Jackson Square

Top reasons to visit Jackson Square

  • Stunning Sunsets: Enjoy breathtaking sunsets at Jackson Square, a perfect spot for memorable evening views.
  • Vibrant Festivals: Experience lively local festivals that showcase the culture and spirit of Key West.
  • Diverse Shopping: Explore unique shops offering local crafts, souvenirs, and more in the surrounding area.
  • Cultural Attractions: Visit nearby museums and art galleries to immerse yourself in the rich local culture.
  • Exciting Nightlife: Experience a vibrant nightlife with various bars and live jazz music just steps away.

Find great hotels near Jackson Square

Discover the charm of Jackson Square in Key West, Florida, where a variety of lodging options await you. From cozy bed and breakfasts to luxurious resorts, you'll find the perfect place to unwind. Whether you're seeking adventure, a historic getaway, or a romantic escape, the hotels near Jackson Square offer exceptional amenities and experiences. Explore top-rated accommodations and read reviews to select your favorite hotel for an unforgettable vacation.

  • La Concha Key West, Autograph Collection: This 4-star hotel is a vibrant blend of adventure and city life, located a mere 161m from Jackson Square. La Concha Key West is the ideal choice for LGBTQIA travelers seeking a welcoming atmosphere and an exciting vacation experience. The hotel's affiliation with LGBTQI travel guides highlights its commitment to inclusivity. Guests can indulge in a variety of adventure sports, including nearby skydiving, snorkeling, and windsurfing. With its prime location in the city center, La Concha offers easy access to local attractions while providing a comfortable retreat with modern amenities.
  • Opal Key Resort & Marina, Key West: Situated 483m from Jackson Square, Opal Key Resort & Marina is a pet-friendly 4-star haven for adventure seekers. This stunning property offers an array of recreational activities, including onsite parasailing and snorkeling, as well as nearby fishing and hiking options. The resort's pet policy allows dogs and service animals, making it an excellent choice for travelers who want to bring their furry companions along. With its picturesque marina views and luxurious amenities, Opal Key ensures a delightful stay for both you and your pet.
  • Heron House - Adult Only: Located only 322m from Jackson Square, Heron House - Adult Only is a charming 3.5-star Bed & Breakfast designed for LGBTQIA travelers seeking an adventure-packed getaway. This intimate property offers a range of nearby activities, such as kayaking, waterskiing, and fishing, all while maintaining a serene atmosphere tailored for adults. With its affiliation with LGBTQI travel guides and welcoming environment, Heron House invites guests to unwind and explore the beauty of Key West in comfort and style.

Where to stay near Jackson Square

Jackson Square in Key West offers an unforgettable travel experience, blending vibrant excursions with a rich historical atmosphere. Nearby parks provide serene spots to relax, while the convenient location makes it easy to explore the lively streets filled with tropical charm. Visitors can enjoy adventure in the surrounding neighborhoods, ensuring an awesome stay. Whether wandering through art galleries or indulging in local cuisine, there’s something for every traveler in this bustling tourist thoroughfare.

  • Key West: Key West is a vibrant island city known for its unique charm and laid-back atmosphere. Located at the southernmost point of the continental United States, it offers a diverse range of experiences for travelers. Whether you're interested in shopping at local boutiques or enjoying the beautiful beaches, Key West has something for everyone. The city’s peak visitor months are January, March, and September, making it a lively destination year-round. Highlights include the famous Duval Street, where you can find numerous restaurants, bars, and art galleries, as well as stunning sunset views at Mallory Square.
  • Key West Historic District: Just 483m from Jackson Square, the Key West Historic District is a treasure trove of history and culture. This neighborhood is characterized by its well-preserved architecture, featuring Victorian-era homes and charming streets. Visitors flock here, especially in March and during the summer months, to soak in its rich heritage. Explore landmarks like the Ernest Hemingway Home and Museum, or take a leisurely stroll along the scenic waterfront. With easy access to shopping areas and resorts, this district is perfect for both relaxation and exploration.
  • Bahama Village: Also located 483m from Jackson Square, Bahama Village offers a taste of the Caribbean spirit in Key West. This lively neighborhood is known for its colorful buildings and vibrant culture, attracting visitors year-round. Peak travel times are in March and during the summer, when the streets come alive with music and festivals. Enjoy local cuisine at quaint eateries, shop for unique souvenirs, and immerse yourself in the lively atmosphere. The close proximity to beautiful beaches makes Bahama Village an ideal spot for family fun and relaxation.

Things to do near Jackson Square

Jackson Square in Key West offers a vibrant mix of activities, including stunning sunsets and lively festivals. Visitors can explore unique shopping spots, enjoy major attractions, and immerse themselves in the local jazz scene at nearby clubs. For those interested in culture, there are several museums to visit, and the nightlife experience is sure to delight with various bars and entertainment options available in the area.

Shopping

For a delightful shopping experience near Jackson Square, visit We Cycle Key West, just 161m away, or head to The Kite House, located 644m from the square. If you're up for a drive, check out the Big Pine Key Flea Market, 46.7km away, for unique finds.

Recreation

At Key West Golf Club, enjoy a round of golf surrounded by lush landscapes, perfect for both relaxation and friendly competition. Nearby, the MLK Community Pool & Community Center offers a refreshing escape with family-friendly vibes and outdoor activities, ideal for unwinding after a day of exploration.

Adventure

In Jackson Square, explore the vibrant street performances and local art scene, immersing yourself in the lively atmosphere. Enjoy delicious Creole cuisine at nearby eateries and take a historic stroll through the charming streets, soaking in the unique culture of Key West.

Nightlife

Experience the vibrant nightlife near Jackson Square with a visit to the Red Barn Theater, just 322m away, offering romance and culture. For more entertainment, enjoy the Waterfront Playhouse at 644m, or indulge in a unique show at the Key West Burlesque Theater, located 1.1km away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Jackson Square

To save money on your trip to Jackson Square, visit during the off-peak months of August to October for better hotel rates. Book your stay about a month in advance or check Expedia for last-minute deals, especially on Tuesdays, which are cheaper than Fridays. Use Expedia's tools to filter for budget-friendly and eco-certified hotels, and consider bundling your hotel, flights, and activities for extra savings. Always compare room rates and look for cancellation options to ensure flexibility in your plans.

  • 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: The cheapest time to book a hotel around Jackson Square is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
  • 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 refine your preferences, such as budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Jackson Square with your flights and activities by booking an Expedia package.

Find the best attractions near Jackson Square

Jackson Square in Key West offers a vibrant blend of historic houses, charming streets, and a lively modern square, perfect for families and culture enthusiasts alike. Explore nearby attractions and immerse yourself in the local culture, from the historic square to various points of interest. Whether you're seeking family-friendly activities or a rich city experience, Jackson Square provides a memorable backdrop for your vacation.

  • Duval Street: Experience the lively atmosphere of Duval Street, known for its vibrant nightlife, eclectic shops, and diverse dining options. Just 161m from Jackson Square, it's the perfect place to soak in the local culture while enjoying street performers and bustling crowds.
  • Mallory Square: Located 644m from Jackson Square, Mallory Square is famous for its stunning sunset celebrations. This modern square offers a mix of entertainment, local art, and spectacular views of the Gulf of Mexico, making it a popular gathering spot.
  • Ernest Hemingway Home and Museum: A short 483m stroll will take you to the Ernest Hemingway Home and Museum. Immerse yourself in the literary history and charming gardens of this historic house, where the renowned author lived and wrote.

Best time to go to Jackson Square

The best time to visit Jackson Square is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.1°F (21.7°C)No RainMostly SunnyAverageAverage
February72.1°F (22.3°C)No RainMostly SunnyAverageSlightly High
March73.4°F (23.0°C)No RainMostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No RainMostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnySlightly HighAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnySlightly LowSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnySlightly LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnySlightly LowAverage
December73.9°F (23.3°C)No RainMostly SunnyAverageAverage

The nearest major airports for your trip to Jackson Square

Traveling to Jackson Square in Key West, Florida, is convenient with two major airports nearby. Key West International Airport (EYW) is situated 4.8km away, offering access to several quality hotels, including the 5-star Casa Marina Key West, 3.2km from the airport, and the 4-star Margaritaville Beach House, only 1.6km away. Both hotels provide easy access to the airport. Alternatively, Florida Keys Marathon Airport (MTH) is located 78.9km from Jackson Square, with nearby lodging options like the 4.5-star Isla Bella Beach Resort & Spa, 6.4km from the airport, and the 4-star Tranquility Bay Beachfront Hotel, 4.8km away, ensuring comfortable stays for travelers.

Frequently asked questions

What's the area like around Jackson Square?
Jackson Square is located in an area of Key West known for its beautiful ocean views, bar scene, and biking. If you're looking for a convenient place to stay, check out the 1801 hotels and other accommodations you'll find within a mile.
Where is the best place to stay close to Jackson Square?
Adjacent to Jackson Square, La Concha Key West, Autograph Collection is one of the top choices for your stay based on our traveler data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include The Cabana Inn Key West - Adults Only and Heron House - Adult Only.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1801 hotels and other accommodations within a mile from Jackson Square.
If I need to cancel the hotel reservation for my stay near Jackson Square, will I receive a refund?
Yes! The majority of hotel bookings are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals near Jackson Square.
Where can I learn more about changing or cancelling my trip in the area near Jackson Square?
For more information about updating your stay near Jackson Square or cancelling it, click here.
What can I see and do near Jackson Square?
Harry S. Truman Little White House, Audubon House and Tropical Gardens, and Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Key West Lighthouse and Keeper's Quarters Museum, Key West Historic Seaport, and Fort Zachary Taylor Historic State Park are some of the local landmarks to explore. You can check out the local talent at Key West Film Society, Red Barn Theater, and Waterfront Playhouse.

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