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 369

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Check prices for these dates

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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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 766
AED 862 total
includes taxes & fees
12 Oct - 13 Oct
Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United States
Maricela
AED 549
AED 679 total
includes taxes & fees
11 Oct - 12 Oct
Douglas House - Adults Only

3. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Carmen
AED 1,172
AED 1,566 total
includes taxes & fees
11 Oct - 12 Oct
H2O Suites - Adults Only

4. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.1 km from Jackson Square
United States
Nestor
AED 713
AED 951 total
includes taxes & fees
11 Oct - 12 Oct
Alexander's Guesthouse - Adult Exclusive

5. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
Nicholas
AED 752
AED 846 total
includes taxes & fees
13 Oct - 14 Oct
Orchid Key Inn - Adults Only

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Forrest
AED 1,030
AED 1,158 total
includes taxes & fees
14 Oct - 15 Oct
The Gardens Hotel

7. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
AED 1,245
AED 1,607 total
includes taxes & fees
12 Oct - 13 Oct
The Marquesa Hotel

8. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United Kingdom
Adam
AED 926
AED 1,041 total
includes taxes & fees
12 Oct - 13 Oct
The Mermaid & Alligator

9. 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
12 Oct - 13 Oct
Santa Maria Suites

10. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Christopher
AED 639
AED 797 total
includes taxes & fees
14 Oct - 15 Oct
Duval House

11. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Riley
AED 521
AED 586 total
includes taxes & fees
12 Oct - 13 Oct
Coco Plum Inn

12. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
Tricia
AED 537
AED 604 total
includes taxes & fees
11 Oct - 12 Oct
Ambrosia Key West

13. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.2 km from Jackson Square
United States
Andrew
AED 521
AED 586 total
includes taxes & fees
11 Oct - 12 Oct
Alexander Palms Court

14. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.2 km from Jackson Square
United States
Richard
AED 592
AED 666 total
includes taxes & fees
26 Oct - 27 Oct
L'Habitation Guest House - Adults Only

15. Authors of Key West Guest House

Authors of Key West Guest House
The Meadows, 1.2 km from Jackson Square
United States
Robbie
AED 328
AED 369 total
includes taxes & fees
12 Oct - 13 Oct
Authors of Key West Guest House

16. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West, 0.5 km from Jackson Square
United States
Susan
AED 951
AED 1,215 total
includes taxes & fees
11 Oct - 12 Oct
Opal Key Resort & Marina, Key West

17. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.7 km from Jackson Square
United States
Keith
AED 743
AED 1,067 total
includes taxes & fees
26 Oct - 27 Oct
The Marker Key West Harbor Resort

18. Caribbean House

Caribbean House
Bahama Village, 0.4 km from Jackson Square
United States
Kelsie
AED 437
AED 583 total
includes taxes & fees
11 Oct - 12 Oct
Caribbean House

19. Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
Downtown Key West, 0.5 km from Jackson Square
United States
Mary
AED 518
AED 766 total
includes taxes & fees
15 Oct - 16 Oct
Paradise Inn Key West - Adults Only

20. Heron House - Adult Only

Heron House - Adult Only
Downtown Key West, 0.3 km from Jackson Square
United States
Fernando
AED 442
AED 620 total
includes taxes & fees
11 Oct - 12 Oct
Heron House - Adult Only
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
1,005 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
550 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
9.8
Exceptional
664 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
171 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,004 reviews
View

Top Jackson Square Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"We always love staying here"
Elizabeth 2-night trip
Posted 11 hours ago
Winslow's Bungalows - Key West Historic Inns
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

10/10 Excellent
"The staff were friendly and helpful."
Jeff 2-night trip
Posted 23 hours ago
Paradise Inn Key West - Adults Only
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

8/10 Good
"Great location & easy check-in! We enjoyed our room and the beautiful inn! Improvements would be: communication - we did not see a single person who works there the entire stay and no response to inquiries. For example, we had a great jacuzzi tub but could not use it as there was no plug, Door to balcony was blocked and could not open. Laundry was always full of inn towels and sheets. Side doors were left open, so security was limited. Despite these things, we most likely would stay again!"
Melissa 2-night trip
Posted 1 day ago
Amsterdam's Curry Mansion Inn
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Location, location, location — and a little paradise in Key West! This was our first-ever visit to Key West, and we chose The Gardens Hotel mainly because of its proximity to Duval Street, Old Town, restaurants, bars, and attractions. It turned out to be a great choice. The hotel is literally one block from Duval Street, and I cannot emphasize enough how important that one block is! You are close enough to walk everywhere, but at night you are away from the noise and can actually enjoy a peaceful night’s sleep. Once you step through the gates of The Gardens Hotel, it feels like entering your own little tropical paradise. The property really lives up to its name. The swimming pool is surrounded by beautiful, lush gardens that feel natural rather than overly manicured. You are truly among nature — frogs, pigeons, little lizards/chameleons, and yes, even the occasional tropical bug! It is Key West, after all. The buildings are older and full of charm, which gives the hotel a wonderful personality. We could understand why some guests told us they return year after year. Everyone was friendly, but a special mention has to go to Annette, the wonderful Irish bartender and chef. What a great host! She made us feel so welcome, and we absolutely loved her. Key West was hot and muggy during our stay, so the pool became a perfect place to cool off between morning sightseeing and going out again in the evening. The poolside bar is well stocked, and the hotel also has a wine bar."
Goutam 4-night trip
Posted 1 day ago
The Gardens Hotel
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Perfect! Great surroundings, staff & people! Convenient to get to everything!"
Diahann 5-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Wonderful place at a great location"
THOMAS 2-night trip
Posted 2 days ago
La Concha Key West, Autograph Collection
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Near Duvall street but still quiet."
Eric 4-night trip
Posted 2 days ago
The Cabana Inn Key West - Adults Only
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"I’ve been to Key West many times, the Heron House is by far the best property we have stayed at. Perfect location to walk to Duval, Mallory Square. Great pool, friendly staff."
Erin 3-night trip
Posted 7 days ago
Heron House - Adult Only
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Fabulous room with the most comfortable bed and pillows. Staff were so friendly and helpful. The pool area cosy and welcoming. Oasis of paradise. Overall our stay at this hotel was fabulous. Mark on reception was very welcoming."
sharon 2-night trip
Posted 3 weeks ago
The Marquesa Hotel

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.