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

Find hotels near Jackson Square, Key West from NT$3,629

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Sep 27 - Sep 28
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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
NT$5,121
NT$5,761 total
includes taxes & fees
Sep 30 - Oct 1
Almond Tree Inn Hotel - Adults Only

2. Artist House Key West

Artist House Key West
Historic Seaport, 0.3 km from Jackson Square
United States
NATHAN
NT$3,226
NT$3,629 total
includes taxes & fees
Oct 11 - Oct 12
Artist House Key West

3. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Forrest
NT$8,901
NT$10,014 total
includes taxes & fees
Oct 27 - Oct 28
The Gardens Hotel

4. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.1 km from Jackson Square
United States
Nestor
NT$2,834
NT$4,379 total
includes taxes & fees
Sep 28 - Sep 29
Alexander's Guesthouse - Adult Exclusive

5. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
John
NT$6,021
NT$6,773 total
includes taxes & fees
Sep 28 - Sep 29
The Conch House Heritage Inn

6. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Corey
NT$8,860
NT$12,111 total
includes taxes & fees
Sep 28 - Sep 29
H2O Suites - Adults Only

7. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
NT$8,542
NT$11,396 total
includes taxes & fees
Sep 28 - Sep 29
The Marquesa Hotel

8. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United States
michael
NT$3,742
NT$4,631 total
includes taxes & fees
Sep 28 - Sep 29
Douglas House - Adults Only

9. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Osvaldo
NT$4,882
NT$5,493 total
includes taxes & fees
Sep 28 - Sep 29
Island City House Hotel

10. Tropical Inn

Tropical Inn
Downtown Key West, 0.4 km from Jackson Square
United States
Molly
NT$3,063
NT$4,240 total
includes taxes & fees
Sep 28 - Sep 29
Tropical Inn

11. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Travis
NT$3,582
NT$4,824 total
includes taxes & fees
Sep 30 - Oct 1
The Grand Guesthouse

12. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Brian
NT$9,527
NT$10,717 total
includes taxes & fees
Oct 28 - Oct 29
The Mermaid & Alligator

13. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Christopher
NT$3,430
NT$4,541 total
includes taxes & fees
Oct 5 - Oct 6
Duval House

14. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Anthony
NT$7,907
NT$11,039 total
includes taxes & fees
Sep 28 - Sep 29
Santa Maria Suites

15. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.2 km from Jackson Square
United States
Andrew
NT$3,787
NT$4,260 total
includes taxes & fees
Sep 28 - Sep 29
Alexander Palms Court

16. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
Tricia
NT$4,263
NT$4,796 total
includes taxes & fees
Sep 28 - Sep 29
Ambrosia Key West

17. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Riley
NT$4,263
NT$4,796 total
includes taxes & fees
Sep 29 - Sep 30
Coco Plum Inn

18. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
sam
NT$2,544
NT$5,005 total
includes taxes & fees
Sep 28 - Sep 29
Silver Palms Inn & Historic Homes

19. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Anthony
NT$4,430
NT$4,984 total
includes taxes & fees
Sep 28 - Sep 29
Westwinds Inn

20. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 km from Jackson Square
United States
yessy
NT$4,423
NT$8,995 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost House - Adult Exclusive
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Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,007 reviews
View
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
Artist House Key West
9.8
Exceptional
456 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,003 reviews
View
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
Alexander's Guesthouse - Adult Exclusive
9.8
Exceptional
169 reviews
View
A porch with a white railing, a bench, and a flag.
The Conch House Heritage Inn
9.8
Exceptional
190 reviews
View

Top Jackson Square Hotel Reviews

Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"Amazing , definitely stay there again!"
Jason 2-night trip
Posted less than an hour ago
Heron House - Adult Only
Douglas House - Adults Only

Douglas House - Adults Only

10/10 Excellent
"Amazing!"
christopher 1-night trip
Posted 1 hour ago
Douglas House - Adults Only
Tranquility Guest House

Tranquility Guest House

10/10 Excellent
"Very quiet. Great location Def would stay here again"
Matthew 3-night trip
Posted 2 hours ago
Tranquility Guest House
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We loved the property, staff, room, but was unable to enjoy the beach at the hotel and was not notified beach was not going to be opened. We picked this hotel for the beach access and didn’t find out the beach was not available until we went down to the beach to relax."
Ana 3-night trip
Posted 2 hours ago
Southernmost Beach Resort and Guesthouses
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Excellent Hotel, staff very helpful and room was excellent. Breakfast was included which was delicious. Beautiful surrounding gardens. Highly recommend"
Richard 2-night trip
Posted 18 hours ago
The Gardens Hotel
Pegasus International Hotel

Pegasus International Hotel

8/10 Good
"I like this property. it was clean, comfortable and the pool was great. The only reason I gave it a 4 instead of a 5 is the check in was very odd as the lobby closed at 6pm and no one answered the phone # posted on the door. We started to panic after about 10 to 15 minutes standing at the door waiting and not knowing if we were going to have a hotel. Luckly right about the time I started to reach out to Expedia to complain my phone rang and it was the hotel lady who then came and got us checked in from there. I would stay here again."
Raymond 2-night trip
Posted 20 hours ago
Pegasus International Hotel
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Great location"
Mary 5-night trip
Posted 22 hours ago
La Concha Key West, Autograph Collection
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

8/10 Good
"Loved the breakfast. The restaurant by the pool was closed early afternoon did not have the happy hour lack of communication with anything to do with amenities need more signage regarding early closing of amenities"
Mary 3-night trip
Posted 1 day ago
Lighthouse Hotel - Key West Historic Inns
Duval House

Duval House

10/10 Excellent
"Fly in, Uber to and from the Duvall, fly home! Great place to have a fun time!"
Anthony 1-night trip
Posted 2 days ago
Duval House

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)
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
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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

  • Vibrant Atmosphere: Jackson Square offers a lively mix of tropical charm and rich history, making it a perfect spot for visitors.
  • Stunning Sunsets: Enjoy breathtaking sunsets at nearby parks like Mallory Square, known for its street performances.
  • Cultural Exploration: Discover historic houses, art galleries, and unique shops that showcase the local culture.
  • Live Jazz Performances: Experience captivating jazz music that enhances the vibrant ambiance of the area.
  • Diverse Accommodations: Choose from charming bed & breakfasts to luxurious resorts for a perfect stay.

Find great hotels near Jackson Square

Explore a variety of hotel accommodations in Jackson Square, Key West, Florida, where you can find everything from charming bed & breakfasts to luxurious resorts. This vibrant area is perfect for adventure seekers and couples looking for a romantic getaway, all while immersing themselves in the local history. Whether you're searching for top hotels or hidden gems, you'll discover excellent reviews and favorite spots that cater to your vacation needs.

  • La Concha Key West, Autograph Collection: Embrace the charm of Key West at La Concha, a 4-star hotel situated a mere 161m from Jackson Square. This property offers a welcoming atmosphere for families, pet owners, and LGBTQIA travelers, making it an inclusive retreat for all. The hotel features kid-friendly amenities such as cribs and window guards, ensuring a safe environment for little ones. Pets are also welcome, with specific policies in place to accommodate furry friends. Guests can enjoy a blend of classic and contemporary decor, a lively bar scene, and easy access to the vibrant local culture.
  • Opal Key Resort & Marina, Key West: Just 483m from Jackson Square, the Opal Key Resort & Marina stands out as a 4-star haven for adventure seekers and pet lovers alike. This resort offers an array of thrilling activities, including snorkeling, boat tours, and parasailing, perfect for those looking to explore the breathtaking waters of Key West. With pet-friendly policies and amenities that cater to dogs, this resort ensures that no family member gets left behind during your vacation. The stunning waterfront views and luxurious accommodations provide a perfect backdrop for relaxation after a day of adventure.
  • Heron House - Adult Only: Nestled only 322m from Jackson Square, Heron House is a charming 3.5-star bed and breakfast exclusively for adults. Ideal for LGBTQIA travelers and adventure enthusiasts, this property offers nearby activities such as sailing, kayaking, and windsurfing. With its intimate atmosphere, guests can unwind in beautifully appointed rooms while enjoying a relaxed, social environment. The B&B's commitment to providing personalized service and a tranquil retreat makes it a perfect choice for those seeking a peaceful getaway in the heart of Key West.

Where to stay near Jackson Square

Visitors to Jackson Square in Key West will be captivated by its vibrant atmosphere, blending tropical charm with rich history. Explore the nearby parks, such as Mallory Square, where you can enjoy stunning sunsets and lively street performances. The area is conveniently located, making it easy to wander through charming neighborhoods filled with art galleries and unique shops. Experience the perfect blend of adventure and relaxation in this must-visit tourist destination.

  • Key West: Nestled at the southernmost point of the continental United States, Key West is a vibrant island city renowned for its laid-back atmosphere and stunning coastal views. Visitors can immerse themselves in a variety of activities, from exploring local shops and dining at waterfront restaurants to indulging in water sports. The city is a hub for families, business travelers, and those seeking a unique urban experience. Key landmarks include the picturesque beaches and lively streets filled with art and culture, making it an ideal destination for all types of travelers.
  • Old Town Key West: Old Town Key West is a charming neighborhood brimming with historic charm and tropical character. Located in close proximity to Jackson Square, this area is perfect for leisurely strolls along its bustling streets lined with quaint shops, galleries, and restaurants. The atmosphere is vibrant, attracting families and business travelers alike. Visitors can experience the local culture while relaxing on family-friendly beaches or exploring the area's rich history, ensuring an enjoyable trip filled with excitement and discovery.
  • Key West Historic District: Just a short walk from Jackson Square, the Key West Historic District offers a glimpse into the island's storied past with its well-preserved architecture and historical landmarks. This neighborhood is popular for its city-themed experiences, making it a perfect spot for families and business travelers. Guests can explore charming streets that lead to inviting beaches and family-friendly recreational areas. With an array of shops and restaurants nearby, the Historic District provides a delightful blend of history and modern conveniences, ensuring a memorable visit.

Things to do near Jackson Square

Jackson Square in Key West offers a vibrant mix of activities for tourists, including stunning sunsets and lively festivals. Explore nearby museums and major attractions, or immerse yourself in the local nightlife. Don't miss out on captivating jazz performances that bring the area to life. Whether biking around the square or enjoying a leisurely stroll, there's something for everyone to enjoy in this iconic destination.

Shopping

Your shopping experience in Jackson Square includes We Cycle Key West, a bike shop 161m away, and The Kite House, a fun store 644m away. If you're up for a drive, visit the Big Pine Key Flea Market, located 46.7km away, for unique local finds.

Recreation

At Key West Golf Club, enjoy a refreshing round of golf surrounded by lush landscapes and a vibrant outdoor atmosphere, just 6.4km from Jackson Square. For a family-friendly experience, visit MLK Community Pool & Community Center, located 805m away, offering a fun and active environment for all ages.

Adventure

Jackson Square is a vibrant hub in Key West, surrounded by historic architecture and lively street performances. Explore local art galleries, enjoy delicious cuisine at nearby cafés, or join a guided ghost tour for a thrilling experience under the stars. Don't miss the stunning sunset views.

Nightlife

Experience the vibrant nightlife at Jackson Square with a visit to the Red Barn Theater, just 322m away, offering romance and entertainment. A short stroll to the Waterfront Playhouse (644m) and the Key West Burlesque Theater (1.1km) will immerse you in the local culture and fun.

*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, plan your visit between August and October when hotel prices are lower. Book your accommodations about a month in advance, and consider checking Expedia for last-minute deals, particularly on Tuesdays, which tend to be the cheapest days. Look for eco-certified hotels for sustainable options. Combine your hotel, flights, and activities into a package deal for additional savings. Finally, explore the area on foot to avoid transportation costs and enjoy free local attractions.

  • 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: Booking a hotel around Jackson Square about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
  • 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 your budget, preferred location, and type of hotel you desire. For instance, selecting the Eco-certified option will reveal sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay at Jackson Square with your flights and activities through an Expedia package deal.

Find the best attractions near Jackson Square

Jackson Square in Key West, Florida, offers a vibrant mix of historic houses, lively streets, and a modern square, perfect for culture enthusiasts and families alike. Visitors can explore nearby attractions, including iconic landmarks and local hotspots, while enjoying the rich history and vibrant atmosphere of this charming area. Don't miss the chance to experience the best of what Jackson Square has to offer.

  • Duval Street: Experience the vibrant energy of Duval Street, a popular thoroughfare filled with lively bars, eclectic shops, and delicious restaurants. This iconic street is perfect for leisurely strolls, where you can soak in the local atmosphere and enjoy the colorful street art.
  • Mallory Square: Known for its stunning sunsets, Mallory Square is a bustling hub of activity. Join the nightly Sunset Celebration, where street performers, artists, and food vendors create an unforgettable experience as the sun dips below the horizon.
  • Ernest Hemingway Home and Museum: Dive into literary history at the Ernest Hemingway Home and Museum. Explore the beautifully preserved residence and lush gardens, gaining insight into the life and works of one of America's greatest writers.

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

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 nearby accommodation options such as the 5-star Casa Marina Key West, Curio Collection by Hilton, just 3.2km from the airport, and the 4-star Margaritaville Beach House Key West, only 1.6km away. Florida Keys Marathon Airport (MTH) is 78.9km from Jackson Square, offering hotels like the 4.5-star Isla Bella Beach Resort & Spa, 6.4km away, and Faro Blanco Resort & Yacht Club, also 4.8km from the airport. Both airports provide convenient access to local transportation services for easy travel to your hotel.

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 1672 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 Pier House Resort & Spa.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1672 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 Fort East Martello Museum and Gallery are some of the local landmarks to explore. You can check out the local talent at Red Barn Theater, Waterfront Playhouse, and Key West Film Society.

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