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

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Check prices for these dates

Tonight
15 Aug - 16 Aug
Tomorrow
16 Aug - 17 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

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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
Michelle
SAR 678
SAR 763 total
includes taxes & fees
17 Aug - 18 Aug
Almond Tree Inn Hotel - Adults Only

2. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
William
SAR 678
SAR 763 total
includes taxes & fees
17 Aug - 18 Aug
Orchid Key Inn - Adults Only

3. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Johnny
SAR 770
SAR 867 total
includes taxes & fees
16 Aug - 17 Aug
The Mermaid & Alligator

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Janeatta
SAR 756
SAR 851 total
includes taxes & fees
8 Sep - 9 Sep
The Gardens Hotel

5. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
SAR 848
SAR 1,166 total
includes taxes & fees
30 Aug - 31 Aug
The Marquesa Hotel

6. 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 348
SAR 533 total
includes taxes & fees
17 Aug - 18 Aug
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

7. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Melissa
SAR 409
SAR 541 total
includes taxes & fees
31 Aug - 1 Sep
Duval House

8. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Amelia
SAR 643
SAR 724 total
includes taxes & fees
16 Aug - 17 Aug
Island City House Hotel

9. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Dan
SAR 560
SAR 724 total
includes taxes & fees
19 Aug - 20 Aug
The Grand Guesthouse

10. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United Kingdom
Dylan
SAR 379
SAR 469 total
includes taxes & fees
27 Aug - 28 Aug
Douglas House - Adults Only

11. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Nila
SAR 1,047
SAR 1,432 total
includes taxes & fees
27 Aug - 28 Aug
Santa Maria Suites

12. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
Patrice
SAR 300
SAR 591 total
includes taxes & fees
16 Aug - 17 Aug
Silver Palms Inn & Historic Homes

13. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Jake
SAR 603
SAR 678 total
includes taxes & fees
30 Aug - 31 Aug
Coco Plum Inn

14. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.3 km from Jackson Square
United States
Sheldon L
SAR 672
SAR 756 total
includes taxes & fees
26 Aug - 27 Aug
Weatherstation Inn

15. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Karen
SAR 498
SAR 560 total
includes taxes & fees
17 Aug - 18 Aug
Westwinds Inn

16. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
Jenina
SAR 710
SAR 798 total
includes taxes & fees
27 Aug - 28 Aug
Ambrosia Key West

17. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 km from Jackson Square
United States
Mark
SAR 523
SAR 1,064 total
includes taxes & fees
30 Aug - 31 Aug
Southernmost House - Adult Exclusive

18. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West, 0.5 km from Jackson Square
United States
Karri
SAR 845
SAR 1,140 total
includes taxes & fees
16 Aug - 17 Aug
Ella's Cottages - Key West Historic Inns

19. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, < 0.1 km from Jackson Square
United States
Dane
SAR 822
SAR 925 total
includes taxes & fees
16 Aug - 17 Aug
Marrero's Guest Mansion

20. Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
Downtown Key West, 0.5 km from Jackson Square
United States
ORLANDO
SAR 378
SAR 594 total
includes taxes & fees
25 Aug - 26 Aug
Paradise Inn Key West - Adults Only
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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
1,017 reviews
View
Property grounds
Orchid Key Inn - Adults Only
9.8
Exceptional
1,010 reviews
View
Audubon Room - Adult Exclusive | Terrace/patio
The Mermaid & Alligator
9.8
Exceptional
312 reviews
View
Exterior detail
The Gardens Hotel
9.8
Exceptional
1,003 reviews
View
Exterior
The Marquesa Hotel
9.8
Exceptional
1,007 reviews
View

Top Jackson Square Hotel Reviews

Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Nice place"
daniel 2-night trip
Posted less than an hour ago
Weatherstation Inn
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"AWSOME FOOD AT RESTAURANTS GREAT SERVICE"
Patrice 3-night trip
Posted 17 hours ago
Opal Key Resort & Marina, Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Beautiful beach, helpful staff"
Cynthia 2-night trip
Posted 18 hours ago
Pier House Resort & Spa
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Beautiful property, relaxing and enjoyable atmosphere, exceptional customer service!"
Janeatta 5-night trip
Posted 19 hours ago
The Gardens Hotel
L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only

10/10 Excellent
"The staff was awesome. The location was perfect with access to duval and the surrounding area all in walking distance. Would stay here again!"
Tawny 2-night trip
Posted 1 day ago
L'Habitation Guest House - Adults Only
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

8/10 Good
"The location is great, it’s very close to most things and only a few minute walk to either end of Duval St. The property is nice, and perfect for my wife and I. we’ve been going to Key West for over 20 years and prefer the authentic Key West Inns vs more corporate properties. We stayed in a loft suite which was fine but had a few broken things which were non-issues for us, but might bug someone"
David 4-night trip
Posted 2 days ago
The Cabana Inn Key West - Adults Only
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Location is directly in old town area of Key West. Convenient walk to Mallory Square. Sunset Pier, Sloppy Joe's, Hogs Breath Salon and various other local hot spots and shops."
Barry 3-night trip
Posted 2 days ago
La Concha Key West, Autograph Collection
Heron House - Adult Only

Heron House - Adult Only

8/10 Good
"Do NOT let the photos fool you on breakfast. Breakfast really really lacked. It was hard boiled eggs, deli meat, yogurts, and I think some pastries. We were really disappointed. I also booked the Tropical King based off the picture of the large tub stating it was "Tropical King." We did not get the nice tub. It was a standard shower/tub combo. Room was good, however, the space around the AC was open and allowed a lot of hot air into the room. Location to Duval St was great. Easy walk to bars and then back home. It was also nice having no children on site. Pool was nice but a bit warm for my liking."
Jessica 2-night trip
Posted 3 days ago
Heron House - Adult Only
Marrero's Guest Mansion

Marrero's Guest Mansion

8/10 Good
"Great location. Quiet"
Damon 6-night trip
Posted 4 days 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 1675 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 1675 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, Ernest Hemingway Home and Museum, and Florida Keys Eco - Discovery Center 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 Waterfront Playhouse, Key West Film Society, and The Key West Theater.