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

Find hotels near Jackson Square, Key West from AED 616

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Check prices for these dates

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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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
AED 1,021
AED 1,149 total
includes taxes & fees
27 Oct - 28 Oct
Almond Tree Inn Hotel - Adults Only

2. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Corey
AED 1,208
AED 1,607 total
includes taxes & fees
26 Oct - 27 Oct
H2O Suites - Adults Only

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
ben
AED 1,068
AED 1,201 total
includes taxes & fees
1 Nov - 2 Nov
Orchid Key Inn - Adults Only

4. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
Jennifer
AED 1,049
AED 1,180 total
includes taxes & fees
25 Oct - 26 Oct
The Conch House Heritage Inn

5. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Gisele
AED 1,236
AED 1,390 total
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel

6. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.4 km from Jackson Square
United States
William
AED 621
AED 698 total
includes taxes & fees
25 Oct - 26 Oct
Simonton Court Historic Inn & Cottages

7. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Justyn
AED 578
AED 742 total
includes taxes & fees
27 Oct - 28 Oct
The Grand Guesthouse

8. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Anthony
AED 1,098
AED 1,483 total
includes taxes & fees
26 Oct - 27 Oct
Santa Maria Suites

9. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Elise
AED 782
AED 880 total
includes taxes & fees
28 Oct - 29 Oct
Island City House Hotel

10. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Cathrine
AED 621
AED 777 total
includes taxes & fees
25 Oct - 26 Oct
Duval House

11. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United Kingdom
Adam
AED 879
AED 989 total
includes taxes & fees
19 Oct - 20 Oct
The Mermaid & Alligator

12. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
sam
AED 327
AED 616 total
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes

13. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 km from Jackson Square
United States
Amy
AED 658
AED 1,205 total
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive

14. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
RICHARD
AED 799
AED 899 total
includes taxes & fees
26 Oct - 27 Oct
Ambrosia Key West

15. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Anthony
AED 547
AED 616 total
includes taxes & fees
28 Oct - 29 Oct
Westwinds Inn

16. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Riley
AED 736
AED 827 total
includes taxes & fees
18 Oct - 19 Oct
Coco Plum Inn

17. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.2 km from Jackson Square
United States
Andrew
AED 826
AED 930 total
includes taxes & fees
19 Oct - 20 Oct
Alexander Palms Court

18. The Independent Inn-Adults only

The Independent Inn-Adults only
Historic Seaport, 1 km from Jackson Square
United States
Michael
AED 554
AED 750 total
includes taxes & fees
18 Oct - 19 Oct
The Independent Inn-Adults only

19. Authors of Key West Guest House

Authors of Key West Guest House
The Meadows, 1.2 km from Jackson Square
United States
Robbie
AED 559
AED 629 total
includes taxes & fees
27 Oct - 28 Oct
Authors of Key West Guest House

20. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.7 km from Jackson Square
United States
Lynne
AED 692
AED 1,009 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
View all properties

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
1,001 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
9.8
Exceptional
667 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,000 reviews
View
A porch with a white railing, a bench, and a flag.
The Conch House Heritage Inn
9.8
Exceptional
194 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
1,001 reviews
View

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"👍"
Peter 1-night trip
Posted 9 hours ago
Southernmost Beach Resort and Guesthouses
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"This resort has everything with the best hospitality! I highly recommend this resort for anyone that wants to enjoy Key West with total relaxation! 😎"
Nikki 5-night trip
Posted 13 hours ago
Pier House Resort & Spa
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Fantastic hotel, very clean, helpful staff, awesome Key West vibes, and great location! We were so happy with everything- breakfast at the Cafe featured friendly staff and the best bacon EVER, pool was delightful, room was great. Highly recommend if you are coming to Key West!"
Tara 3-night trip
Posted 14 hours ago
The Marquesa Hotel
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 15 hours ago
La Concha Key West, Autograph Collection
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"The hotel location, cleanliness and view are awesome. No complaints about anything. The unlimited cold water bottles were icing on the cake. If I’m so happy with a partial sea view room, I’ll be even happier with an oceanfront room. Maybe next time."
Vivek 2-night trip
Posted 19 hours ago
Opal Key Resort & Marina, Key West
Pegasus International Hotel

Pegasus International Hotel

10/10 Excellent
"We love staying on Duval Street! The second story deck area with the pool is my favorite spot. We like to sit & relax after a long day and watch the people go by on Duval. Free parking is also a huge bonus in Key West! Easy to unload bags right by the hotel door, then a short half block drive to the lot. We always stay here for our yearly trip to the Keys!"
Linda 3-night trip
Posted 2 days ago
Pegasus International Hotel
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

10/10 Excellent
"Place was great, clean, and reasonable. Beware the roosters at 6am but that might be the entire city of Key West Old Town"
Jason 2-night trip
Posted 4 days ago
Paradise Inn Key West - Adults Only
Coco Plum Inn

Coco Plum Inn

10/10 Excellent
"This B&B was very convenient to Duval Street. The pool area was wonderful with places to sit and get together with our friends. We found the bed and pillows to be very comfortable and the manager was phenomenal! We had to check out at 11:00 but needed a place to hang out until 4:00 to catch the ferry. We were allowed to store our luggage and make use of the pool. We would definitely stay at Coco Plum again if we ever go back to Key West."
Karen 3-night trip
Posted 5 days ago
Coco Plum Inn
Tranquility Guest House

Tranquility Guest House

10/10 Excellent
"Lived up to its name-very tranquil. Well decorated interior with an ‘old Key West vibe’ but with updated modern bathroom. Nice pool area retreat. Location was perfect-walking distance to all major Key West attractions, restaurants, park, etc. This would be first on our list for a return visit!"
Perry 2-night trip
Posted 7 days ago
Tranquility Guest 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)
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 at Jackson Square, a perfect spot for memorable evening views.
  • Vibrant Festivals: Experience lively local festivals that showcase the culture and spirit of Key West.
  • Diverse Shopping: Explore unique shops offering local crafts, souvenirs, and more in the surrounding area.
  • Cultural Attractions: Visit nearby museums and art galleries to immerse yourself in the rich local culture.
  • Exciting Nightlife: Experience a vibrant nightlife with various bars and live jazz music just steps away.

Find great hotels near Jackson Square

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

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

Where to stay near Jackson Square

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

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

Things to do near Jackson Square

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

Shopping

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

Recreation

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

Adventure

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

Nightlife

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

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

Booking tips and Expedia advantages for Jackson Square

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

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

Find the best attractions near Jackson Square

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

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

Best time to go to Jackson Square

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

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

The nearest major airports for your trip to Jackson Square

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

Frequently asked questions

What's the area like around Jackson Square?
Jackson Square is located in an area of Key West known for its beautiful ocean views, bar scene, and biking. If you're looking for a convenient place to stay, check out the 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, 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, 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, Key West Film Society, and The Key West Theater.