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Our top choices for Jackson Square hotels

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Downtown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1,008 reviews)
"perfect location close the action but still in quieter are, nice staff, highly recommend for a stay in Key West"
United States
stephane
The price is NT$12,089
NT$13,601 total
includes taxes & fees
May 10 - May 11
Almond Tree Inn Hotel - Adults Only

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1,002 reviews)
"Enjoyed our stay, loved the location. Hotel and staff were friendly and accommodating."
United States
Mark
The price is NT$10,856
NT$12,212 total
includes taxes & fees
Apr 13 - Apr 14
Orchid Key Inn - Adults Only

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (391 reviews)
"This place is a gem with Lovely accommodations,peaceful pooland great staff we will always come back when in KW. "
United States
Garda
The price is NT$9,833
NT$11,858 total
includes taxes & fees
Apr 12 - Apr 13
Tropical Inn

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (594 reviews)
"The highest quality hotel room that I have ever stayed in. Be aware of one thing, NO Restaurant! But hey Frenchie’s cafe around the corner has the best breakfast. H20 was a fantastic stay and surprisingly to us both the pool on the roof and our very own plunge pool were heated and we made use of them both. A fantastic place to stay…"
United Kingdom
Simon
The price is NT$14,601
NT$18,574 total
includes taxes & fees
May 10 - May 11
H2O Suites - Adults Only

Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, < 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (337 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is NT$10,150
NT$11,419 total
includes taxes & fees
May 6 - May 7
Marrero's Guest Mansion

Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,003 reviews)
"The property is beautiful and the location is perfect. It has a lovely chill Key West vibe. Management is on-site and helpful."
United States
Ann Elizabeth
The price is NT$9,492
NT$10,679 total
includes taxes & fees
Apr 13 - Apr 14
Ambrosia Key West

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,001 reviews)
"The location is pretty good, it's about a mile and a little bit more to Mallory square, but there are many things to see along the way. It has a nice Key West vibe to it, especially having the breakfast outside in the morning. And coffee is available 24 hours which we like"
United States
Glenn
The price is NT$7,959
NT$9,749 total
includes taxes & fees
Apr 12 - Apr 13
The Grand Guesthouse

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,000 reviews)
"Wonderful pool "
United States
lloyd
The price is NT$13,965
NT$17,858 total
includes taxes & fees
May 11 - May 12
Santa Maria Suites

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,022 reviews)
"great place. perfect location!"
United States
Janelle
The price is NT$5,984
NT$8,879 total
includes taxes & fees
Apr 12 - Apr 13
Silver Palms Inn

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (1,135 reviews)
"Great location and great accommodation "
United States
robert
The price is NT$8,550
NT$10,814 total
includes taxes & fees
Apr 19 - Apr 20
Heron House - Adult Only

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
4.0 star property
Uptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1,003 reviews)
"Ocean view, great pool & great staff. Excellent place to stay!"
United States
Adam
The price is NT$7,609
NT$12,586 total
includes taxes & fees
May 3 - May 4
Southernmost House - Adult Exclusive

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Downtown Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,010 reviews)
"Wonderful property. Great location. Feels quiet and secluded. We loved the breakfast and the happy hour."
United States
Cindy
The price is NT$7,376
NT$9,729 total
includes taxes & fees
Apr 19 - Apr 20
Paradise Inn Key West - Adults Only

The Key West Hotel

The Key West Hotel
2.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (548 reviews)
"Excellent location on Duval st. Would definitely stay here again."
United States
Deborah S.
The price is NT$11,447
NT$14,628 total
includes taxes & fees
Apr 14 - Apr 15
The Key West Hotel

Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
3.0 star property
Downtown Key West, 0.5 km from Jackson Square
9.0 out of 10, Wonderful, (435 reviews)
"Our Stay was great…perfect location and Room!"
United States
Diana
The price is NT$6,874
NT$9,344 total
includes taxes & fees
Apr 15 - Apr 16
Seascape Tropical Inn - Adult Exclusive

Alexander Palms Court

Alexander Palms Court
2.5 star property
Casa Marina, 1.2 km from Jackson Square
9.2 out of 10, Wonderful, (1,004 reviews)
"Excellent staff, comfortable bed, nice pool, and the entire area was clean."
United States
Richard
The price is NT$10,278
NT$11,563 total
includes taxes & fees
May 3 - May 4
Alexander Palms Court

Duval Inn

Duval Inn
3.0 star property
Downtown Key West, 0.3 km from Jackson Square
8.8 out of 10, Excellent, (765 reviews)
"Perfect location, beautiful rooms and serene garden/pool area to relax! Rent bikes right there and enjoy Key West! "
United States
Kristin
The price is NT$6,986
NT$9,470 total
includes taxes & fees
Apr 13 - Apr 14
Duval Inn

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Historic Seaport, 0.2 km from Jackson Square
8.8 out of 10, Excellent, (372 reviews)
"Nice, clean hotel in a great location "
United States
Hollie
The price is NT$9,448
NT$11,702 total
includes taxes & fees
May 4 - May 5
La Concha Key West, Autograph Collection

Heron House Court - Adult Only

Heron House Court - Adult Only
3.0 star property
Historic Seaport, 1 km from Jackson Square
9.0 out of 10, Wonderful, (1,012 reviews)
"Had a wonderful stay with friendly and helpful staff!"
United States
James
The price is NT$5,464
NT$7,254 total
includes taxes & fees
Apr 16 - Apr 17
Heron House Court - Adult Only

Eden House

Eden House
4.0 star property
Historic Seaport, 0.9 km from Jackson Square
9.0 out of 10, Wonderful, (1,002 reviews)
"The staff and guests were amazing. We will definitely be booking another stay there!"
United States
Shannon
The price is NT$7,036
NT$8,865 total
includes taxes & fees
May 10 - May 11
Eden House

The Palms Hotel

The Palms Hotel
3.0 star property
The Meadows, 1.2 km from Jackson Square
8.8 out of 10, Excellent, (1,006 reviews)
"Enjoyed our stay room was clean. Beds were comfortable would stay again if in the area."
United States
Dawn
The price is NT$6,855
NT$8,427 total
includes taxes & fees
May 5 - May 6
The Palms Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
3.5 star property
10.0
Exceptional
1,008 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,002 reviews
View
11 Gecko's Garden - Adults Only | Premium bedding, pillowtop beds, individually decorated
Tropical Inn
3.5 star property
9.6
Exceptional
391 reviews
View
Deluxe Suite, 1 King Bed, Private Pool | View from room
H2O Suites - Adults Only
3.5 star property
9.8
Exceptional
594 reviews
View
Terrace/patio
Marrero's Guest Mansion
3.5 star property
9.4
Exceptional
337 reviews
View

Top Jackson Square Hotel Reviews

Hotels near other Jackson Square attractions

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 1734 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, The Cabana Inn Key West - Adults Only is one of the top choices for your stay based on our traveler data, and this guesthouse offers free breakfast and an outdoor pool. Other good options close by include Southernmost Beach Resort and Guesthouses and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1734 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, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum, and Key West Historic Seaport are some of the local landmarks to explore. You can check out the local talent at Waterfront Playhouse, Key West Film Society, and Red Barn Theater.

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