The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

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2 Sep - 3 Sep
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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 0.6 km from Jackson Square
United States
John
SAR 634
SAR 713 total
includes taxes & fees
8 Sep - 9 Sep
Almond Tree Inn Hotel - Adults Only

2. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Brian
SAR 630
SAR 709 total
includes taxes & fees
14 Sep - 15 Sep
The Gardens Hotel

3. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Old Town Key West, 1.1 km from Jackson Square
United States
Jaime
SAR 368
SAR 556 total
includes taxes & fees
8 Sep - 9 Sep
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
Nicholas
SAR 605
SAR 681 total
includes taxes & fees
8 Sep - 9 Sep
Orchid Key Inn - Adults Only

5. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.4 km from Jackson Square
United States
Robin
SAR 710
SAR 798 total
includes taxes & fees
8 Sep - 9 Sep
Simonton Court Historic Inn & Cottages

6. The Porch on Frances Inn

The Porch on Frances Inn
Old Town Key West, 1 km from Jackson Square
United States
Corrynne
SAR 427
SAR 593 total
includes taxes & fees
7 Sep - 8 Sep
The Porch on Frances Inn

7. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
SAR 721
SAR 1,022 total
includes taxes & fees
17 Sep - 18 Sep
The Marquesa Hotel

8. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
John
SAR 534
SAR 601 total
includes taxes & fees
13 Sep - 14 Sep
The Conch House Heritage Inn

9. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Shermeka
SAR 943
SAR 1,314 total
includes taxes & fees
14 Sep - 15 Sep
H2O Suites - Adults Only

10. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Robert
SAR 346
SAR 470 total
includes taxes & fees
20 Sep - 21 Sep
Duval House

11. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United States
savannah
SAR 383
SAR 474 total
includes taxes & fees
9 Sep - 10 Sep
Douglas House - Adults Only

12. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Paul
SAR 577
SAR 649 total
includes taxes & fees
7 Sep - 8 Sep
Island City House Hotel

13. Tropical Inn

Tropical Inn
Downtown Key West, 0.4 km from Jackson Square
United States
Joel
SAR 392
SAR 535 total
includes taxes & fees
3 Sep - 4 Sep
Tropical Inn

14. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Johnny
SAR 676
SAR 760 total
includes taxes & fees
28 Sep - 29 Sep
The Mermaid & Alligator

15. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Travis
SAR 480
SAR 634 total
includes taxes & fees
3 Sep - 4 Sep
The Grand Guesthouse

16. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
June Young
SAR 1,048
SAR 1,432 total
includes taxes & fees
8 Sep - 9 Sep
Santa Maria Suites

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
Shawn
SAR 250
SAR 535 total
includes taxes & fees
3 Sep - 4 Sep
Silver Palms Inn & Historic Homes

18. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
John
SAR 436
SAR 491 total
includes taxes & fees
22 Sep - 23 Sep
Westwinds Inn

19. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Jake
SAR 504
SAR 567 total
includes taxes & fees
15 Sep - 16 Sep
Coco Plum Inn

20. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United Kingdom
Kate
SAR 504
SAR 567 total
includes taxes & fees
27 Sep - 28 Sep
Ambrosia Key West
View all properties

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
10.0
Exceptional
1,009 reviews
View
Exterior detail
The Gardens Hotel
9.8
Exceptional
1,000 reviews
View
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | WiFi (free), bed sheets
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
9.8
Exceptional
163 reviews
View
Property grounds
Orchid Key Inn - Adults Only
9.8
Exceptional
1,006 reviews
View
Queen with Pool View | Minibar, in-room safe, iron/ironing board, WiFi (free)
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,002 reviews
View

Top Jackson Square Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Wonderful"
Ka Sing 1-night trip
Posted 3 hours ago
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"The property is so cute. It sits at the end of Duval St which was so convenient. The room and balcony was spotless and came with water restocked everyday. I will say that the “beach” was a muddy mess with huge mud holes. No one was on the “beach”. Other than that, plenty of restaurants within walking distance and even a CVS."
Abigail 2-night trip
Posted 12 hours ago
Southernmost Beach Resort and Guesthouses
Duval House

Duval House

10/10 Excellent
"The Duval House was an excellent place to stay. Very convenient to all the attractions in Key West. The staff were extremely nice. The property is an excellent mix of historic Key West with all the ammenities you need for a great staff. The grounds are very peaceful and well maintained. The apartment room was perfect with a full kitchen and a private deck overlooking Duval Street. I would definitely stay here again if I go back to Key West."
Douglas Robert 1-night trip
Posted 16 hours ago
Duval House
Pegasus International Hotel

Pegasus International Hotel

10/10 Excellent
"Exceptional location, good price for Key West which came with parking. I am definitely going to return to this place and recommend to others !!."
Shahid 1-night trip
Posted 1 day ago
Pegasus International Hotel
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

10/10 Excellent
"Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, a very pleasant stay!"
gabriela 3-night trip
Posted 2 days ago
Lighthouse Hotel - Key West Historic Inns
Duval Inn

Duval Inn

10/10 Excellent
"Honestly, great location and loved our room! The only thing is I don’t think we got our VIP welcome gift. Not the end of the world!"
Courtney 2-night trip
Posted 3 days ago
Duval Inn
Coco Plum Inn

Coco Plum Inn

10/10 Excellent
"The pool is so topically beautiful and clean!! Room was cool and comfortable!! Will definitely be back!"
Shaun 5-night trip
Posted 6 days ago
Coco Plum Inn
Tranquility Guest House

Tranquility Guest House

8/10 Good
"Nice place. Very quiet and peaceful. Some minor amenities would be helpful (coffee pot in the room, ice machine)."
Richard 3-night trip
Posted 9 days ago
Tranquility Guest House
Marrero's Guest Mansion

Marrero's Guest Mansion

10/10 Excellent
"Awesome place to stay!"
Michael 4-night trip
Posted 2 weeks ago
Marrero's Guest Mansion

Other attractions near Jackson Square

A historic building with ornate architecture, a balcony, and a coat of arms.

San Carlos Institute - Casa Cuba

8.6/10 (34 reviews)
You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.
See properties
A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.
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We Cycle Key West

You can search for that perfect souvenir at We Cycle Key West during your trip to Key West.
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St. Paul's Episcopal Church

9.0/10 (73 reviews)
St. Paul's Episcopal Church is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its lively festivals.
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Key West Film Society

7.6/10 (9 reviews)
You can get tickets for a performance at Key West Film Society during your stay in Key West. In the area, take in the lively festivals and beautiful sunsets.
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The Key West Theater

You can make plans for a show at The Key West Theater on your trip to Key West. Discover the area's great live music, or seek out its biking trails.
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Red Barn Theater

8.0/10 (10 reviews)
You can enjoy a show at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.
See properties

Hellings House Museum

You can spend an afternoon exploring the galleries in Hellings House Museum during your trip to Key West. Experience the area's entertainment choices and great live music.
See properties

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 1678 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 Southernmost Beach Resort and Guesthouses and Hyatt Centric Key West Resort and Spa.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1678 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, Mel Fisher Maritime Museum, 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, Fort Zachary Taylor Historic State Park, and Donkey Milk House are some of the local landmarks to explore. You can check out the local talent at Waterfront Playhouse, Key West Film Society, and The Key West Theater.