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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, (1,013 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is SAR 937
SAR 1,054 total
includes taxes & fees
21 May - 22 May
Almond Tree Inn Hotel - Adults Only

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (953 reviews)
"Defiantly would stay again and so close to everything"
United States
kelly
The price is SAR 897
SAR 1,009 total
includes taxes & fees
20 May - 21 May
Simonton Court Historic Inn & Cottages

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,005 reviews)
"Great accommodations and great staff"
United States
Julian
The price is SAR 1,160
SAR 1,516 total
includes taxes & fees
31 May - 1 Jun
The Marquesa Hotel

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (261 reviews)
"This was the best place we have stayed at in Key West! It was super quiet but only a block from Duval. The owners really put a lot of care into the place and are super nice! Definitely would stay there again! "
United States
Jennifer
The price is SAR 773
SAR 870 total
includes taxes & fees
18 May - 19 May
Key West Villas

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, (1,004 reviews)
"This is an amazing place ! If you are coming to Key West you won’t find a nicer place. "
United States
Vicki
The price is SAR 932
SAR 1,049 total
includes taxes & fees
21 May - 22 May
Orchid Key Inn - Adults Only

Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (385 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is SAR 673
SAR 833 total
includes taxes & fees
2 Jun - 3 Jun
Douglas House - Adults Only

Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.6 km from Jackson Square
9.6 out of 10, Exceptional, (999 reviews)
"Nice location "
United States
Michael
The price is SAR 863
SAR 971 total
includes taxes & fees
8 Jun - 9 Jun
Island City House Hotel

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, (980 reviews)
"This was a lovely well stocked, and comfortable stay."
United States
Pat
The price is SAR 658
SAR 741 total
includes taxes & fees
26 May - 27 May
L'Habitation Guest House

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (527 reviews)
"Loved the property and staff was super friendly."
United States
Brinkley
The price is SAR 992
SAR 1,116 total
includes taxes & fees
19 May - 20 May
Coco Plum Inn

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (604 reviews)
"This resort was in the perfect location for exploring Key West. Highly recommend!"
United States
Barton
The price is SAR 1,460
SAR 1,896 total
includes taxes & fees
2 Jun - 3 Jun
H2O Suites - Adults Only

Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, < 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (337 reviews)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is SAR 934
SAR 1,051 total
includes taxes & fees
11 Jun - 12 Jun
Marrero's Guest Mansion

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,040 reviews)
"Nice place clean, good breakfast right on Duval for easy walk to everything "
Canada
Parmjit
The price is SAR 672
SAR 836 total
includes taxes & fees
26 May - 27 May
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, (474 reviews)
"Cute place. Great location to everything on Duval. Service was great and friendly."
United States
DJS Darren Jay
The price is SAR 635
SAR 905 total
includes taxes & fees
26 May - 27 May
Ella's Cottages - Key West Historic Inns

Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,000 reviews)
"Breakfast by the pool was excellent! Pools were nice, with plenty of areas for privacy. We especially enjoyed the private patios and courtyards. Fantastic location!"
United States
Tina
The price is SAR 735
SAR 827 total
includes taxes & fees
27 May - 28 May
Ambrosia Key West

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,018 reviews)
"Very clean rooms staff was very helpful. Pools we’re nice little small you continental breakfast could add a couple more things like bananas all in all 10 out of 10"
United States
Bruce
The price is SAR 895
SAR 1,007 total
includes taxes & fees
26 May - 27 May
Westwinds Inn

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,001 reviews)
"This is a great place to stay, quiet and nice accommodations. Awesome little courtyard for breakfast."
United States
Jacqueline
The price is SAR 552
SAR 715 total
includes taxes & fees
18 May - 19 May
The Grand Guesthouse

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (1,146 reviews)
"Wonderful stay! Loved the property and location. "
United States
Janet
The price is SAR 522
SAR 714 total
includes taxes & fees
17 May - 18 May
Heron House - Adult Only

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,041 reviews)
"Great continental breakfast options. Onsite parking was convenient."
United States
Keith
The price is SAR 436
SAR 743 total
includes taxes & fees
25 May - 26 May
Silver Palms Inn & Historic Homes

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,006 reviews)
"Great hotel and room. Very clean, great location."
United States
Cindy
The price is SAR 1,272
SAR 1,684 total
includes taxes & fees
1 Jun - 2 Jun
Santa Maria Suites

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,099 reviews)
"Amazing stay.. will definitely be back!!!"
United States
Jennifer
The price is SAR 972
SAR 1,241 total
includes taxes & fees
25 May - 26 May
Opal Key Resort & Marina, Key West
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.

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,013 reviews
View
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
953 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,005 reviews
View
Front of property
Key West Villas
3.5 star property
9.8
Exceptional
261 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,004 reviews
View

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 that paint the sky with vibrant colors, creating a picturesque backdrop for your visit.
  • Cultural Hub: Experience a rich blend of art, history, and local culture at this iconic square, perfect for exploration.
  • Lively Nightlife: Discover jazz clubs and vibrant festivals that offer a taste of Key West's energetic nightlife.
  • Charming Accommodations: Choose from a variety of unique hotels and cozy bed and breakfasts for a memorable stay.
  • Outdoor Adventures: Explore nearby parks and biking trails for a fun way to experience the tropical beauty of the area.

Find great hotels near Jackson Square

Jackson Square in Key West offers a variety of charming accommodations, from luxurious resorts to cozy bed and breakfasts. Whether you're seeking adventure, a historic atmosphere, or a romantic getaway, you'll find hotels that cater to your every desire. Explore top-rated options, read reviews, and discover your favorite hotel near Jackson Square to make your vacation unforgettable.

  • La Concha Key West, Autograph Collection: Embrace the spirit of adventure at La Concha Key West, a stunning 4-star hotel located a mere 161m from Jackson Square. This beachfront property caters to families and thrill-seekers alike, offering a plethora of adventure sports such as kayaking, sailing, and even skydiving nearby. The hotel features family-friendly amenities, including complimentary cribs and window guards for children, ensuring a comfortable stay for guests of all ages. With its vibrant atmosphere and proximity to local attractions, La Concha is an ideal choice for those looking to create lasting vacation memories.
  • Opal Key Resort & Marina, Key West: Experience the ultimate getaway at Opal Key Resort & Marina, Key West, located just 483m from Jackson Square. This pet-friendly 4-star resort is perfect for travelers seeking adventure, allowing pets for a fee while providing various outdoor activities like snorkeling, fishing, and parasailing right on the property. Guests can indulge in the resort’s luxurious amenities, which include a stunning marina and easy access to boat tours. Whether you're exploring the waters or relaxing in style, Opal Key is designed to cater to your adventurous spirit and furry companions.
  • Heron House - Adult Only: Discover a welcoming oasis at Heron House - Adult Only, a charming 3.5-star bed and breakfast just 322m from Jackson Square. Ideal for those seeking an adventure-filled stay, this property is LGBTQIA-friendly and affiliated with LGBTQI travel guides. Guests can enjoy activities like surfing, snorkeling, and windsurfing in the nearby area. The serene atmosphere and intimate setting make it a perfect retreat, offering a unique blend of adventure and relaxation for adult travelers. Heron House is dedicated to providing a memorable experience for all who visit.

Where to stay near Jackson Square

Experience the vibrant atmosphere near Jackson Square, Key West, where tropical charm meets rich history. Stroll through nearby parks like Fort Zachary Taylor State Park for outdoor adventure, or enjoy the lively tourist thoroughfare filled with local shops and eateries. With its convenient location, you’ll find an awesome stay that captures the essence of Key West, making it a perfect base for exploring the area’s unique excursions and adventures.

  • Key West: A vibrant island city, Key West is known for its stunning sunsets, lively atmosphere, and rich history. Situated at the southernmost point of the continental United States, it boasts beautiful beaches and a diverse range of activities. Visitors can enjoy shopping at local boutiques, exploring art galleries, or indulging in fresh seafood at waterfront restaurants. The city experiences a steady flow of tourists year-round, with peak seasons in January, March, and September, making it a great destination for family vacations or business trips.
  • Key West Historic District: Located just 483m from Jackson Square, the Key West Historic District is a charming area filled with well-preserved Victorian architecture and a rich cultural heritage. It offers a delightful blend of residential and commercial spaces, making it perfect for leisurely strolls. Visitors can explore quaint shops, dine at local eateries, and immerse themselves in the vibrant history of the island. This neighborhood tends to attract tourists primarily in March and during the summer months, ensuring a bustling atmosphere filled with family-friendly experiences.
  • Bahama Village: Also located 483m away from Jackson Square, Bahama Village is a colorful neighborhood that showcases the Caribbean influence on Key West's culture. Known for its lively streets and friendly locals, this area is a great place to experience authentic Bahamian cuisine and shop for unique crafts. The neighborhood draws visitors throughout the year, particularly during peak times in March and summer, making it an ideal spot for those seeking a city-themed, family-oriented vacation in a culturally rich setting.

Things to do near Jackson Square

While visiting Jackson Square in Key West, Florida, you can enjoy stunning sunsets, vibrant festivals, and biking around the area. Don't miss out on the lively nightlife experience with jazz clubs and unique shopping spots nearby, along with major attractions that highlight the local culture. A trip to Jackson Square promises a blend of entertainment, relaxation, and unforgettable moments.

Shopping

For a quick shopping experience, visit We Cycle Key West, only 161m from Jackson Square, or The Kite House, located 644m away. If you're up for a drive, check out the Big Pine Key Flea Market, a vibrant public market 46.7km from Jackson Square.

Recreation

Experience tranquility at the Key West Golf Club, where you can enjoy a round of golf surrounded by beautiful landscapes, just 6.4km from Jackson Square. For a family-friendly atmosphere, visit the MLK Community Pool & Community Center, located 805m away, offering refreshing swimming and outdoor fun.

Adventure

In Jackson Square, explore the vibrant street performances and local art galleries, immersing yourself in the lively culture. Enjoy delicious cuisine at nearby eateries or take a historic walking tour to discover the rich heritage of Key West, all while soaking up the tropical atmosphere.

Nightlife

In Jackson Square, the Red Barn Theater offers a charming atmosphere just 322m away, while the Waterfront Playhouse, located 644m away, showcases captivating performances. For a unique experience, the Key West Burlesque Theater, 1.1km away, combines romance and entertainment in a lively setting.

*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, consider visiting between August and October when hotel prices are lower. Book your hotel about a month in advance for better rates, and check for last-minute deals on Expedia. Tuesdays tend to be the cheapest nights to stay, while Fridays are the most expensive. Use Expedia's search tool to filter by budget and preferred hotel type, and consider booking a package deal that combines flights, accommodations, and activities for additional savings. Don’t forget to explore free activities in the area to make the most of your visit.

  • 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, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
  • 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 narrow down your preferences, such as budget, desired location, and the type of hotel you’re looking for. 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 near Jackson Square with your flights and activities by booking a package through Expedia.

Find the best attractions near Jackson Square

Jackson Square in Key West offers a rich blend of historic sites, lively streets, and a modern square atmosphere perfect for cultural and family experiences. Visitors can explore nearby attractions, including charming local spots and historic landmarks. Don't miss the vibrant atmosphere of this iconic square, where art, history, and community converge, making it an ideal starting point for your adventure in the heart of Key West.

  • Duval Street: Experience the vibrant energy of Duval Street, known for its lively atmosphere filled with shops, restaurants, and bars. Just a short walk from Jackson Square, this iconic street is perfect for strolling, people-watching, and enjoying the local nightlife.
  • Mallory Square: A hub of activity, Mallory Square is famous for its sunset celebrations. Located 644m from Jackson Square, it offers stunning views of the Gulf of Mexico, street performers, and local artisans, making it a must-visit for an unforgettable evening.
  • Ernest Hemingway Home and Museum: Immerse yourself in literary history at the Ernest Hemingway Home and Museum. Situated 483m from Jackson Square, this historic house showcases the writer's life and work, surrounded by beautiful gardens and charming architecture.

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.

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

To visit Jackson Square in Key West, Florida, you can fly into two major airports. Key West International Airport (EYW) is located 4.8km away, with notable hotels like Casa Marina Key West (3.2km), Margaritaville Beach House (1.6km), and Oceans Edge Key West Resort (3.2km), all offering convenient access. Alternatively, you can fly into Florida Keys Marathon Airport (MTH), which is 78.9km away. Nearby accommodations include Isla Bella Beach Resort & Spa (6.4km), Tranquility Bay Beachfront Hotel (4.8km), and Faro Blanco Resort & Yacht Club (4.8km), providing good options for your stay.

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 1734 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, The Cabana Inn Key West - Adults Only is one of the top choices for your stay based on our traveler data, and this guesthouse offers free breakfast and an outdoor pool. Other good options close by include Southernmost Beach Resort and Guesthouses and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1734 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 Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum, and Fort Zachary Taylor Historic State Park are some of the local landmarks to explore. You can check out the local talent at Waterfront Playhouse, Key West Film Society, and Red Barn Theater.