Find hotels near Jackson Square, Key West from ¥14,288

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Compare 2,682 hotels close to Jackson Square with room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Jackson Square hotels

Simonton Court Historic Inn & Cottages

2.5 star property
9.8 out of 10, Exceptional, (808)
"Awesome place to stay with a great staff"
The price is ¥21,724
¥24,440 total
includes taxes & fees
Sep 10 - Sep 11
Simonton Court Historic Inn & Cottages

The Gardens Hotel

4.0 star property
9.8 out of 10, Exceptional, (1002)
"What a fantastic place this is, very clean and classy. I would stay here again!"
The price is ¥28,471
¥32,030 total
includes taxes & fees
Sep 10 - Sep 11
The Gardens Hotel

Artist House Key West

3.5 star property
9.8 out of 10, Exceptional, (408)
"Very nice B&B close to everything."
The price is ¥17,474
¥19,658 total
includes taxes & fees
Sep 3 - Sep 4
Artist House Key West

The Marquesa Hotel

3.5 star property
9.8 out of 10, Exceptional, (1004)
"Property is nicely maintained staff is extremely attentive and polite"
The price is ¥27,834
¥38,770 total
includes taxes & fees
Sep 15 - Sep 16
The Marquesa Hotel

Coco Plum Inn

3.0 star property
9.6 out of 10, Exceptional, (437)
"Great location, nice staff."
The price is ¥23,725
¥26,692 total
includes taxes & fees
Sep 7 - Sep 8
Coco Plum Inn

Orchid Key Inn - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (1008)
"Excellent friendly staff and beautiful property. "
The price is ¥27,354
¥30,774 total
includes taxes & fees
Sep 4 - Sep 5
Orchid Key Inn - Adults Only

L'Habitation Guest House

2.5 star property
9.4 out of 10, Exceptional, (883)
"Every person I met there on staff was super nice and accommodating"
The price is ¥14,288
¥16,074 total
includes taxes & fees
Sep 4 - Sep 5
L'Habitation Guest House

The Conch House Heritage Inn

3.5 star property
9.8 out of 10, Exceptional, (130)
"We really enjoyed our stay"
The price is ¥29,902
¥33,640 total
includes taxes & fees
Sep 3 - Sep 4
The Conch House Heritage Inn

Island City House Hotel

3.0 star property
9.6 out of 10, Exceptional, (1001)
"Great location. Appreciated having access to a pool and liked the separate living area with kitchen amenities. "
The price is ¥24,410
¥27,461 total
includes taxes & fees
Sep 1 - Sep 2
Island City House Hotel

Weatherstation Inn

2.5 star property
9.4 out of 10, Exceptional, (951)
"The staff went above and beyond for us to have a great vacation and stay! "
The price is ¥24,889
¥28,001 total
includes taxes & fees
Sep 8 - Sep 9
Weatherstation Inn

The Mermaid & Alligator

3.5 star property
9.8 out of 10, Exceptional, (256)
"Absolutely loved staying here and are already looking at dates to come back!"
The Mermaid & Alligator

Marrero's Guest Mansion

3.5 star property
9.4 out of 10, Exceptional, (333)
"The vibes were right! Room #12 in the back poolside solo cottage is fire!! 🔥✌️🧘‍♀️😘 "
The price is ¥21,970
¥24,717 total
includes taxes & fees
Sep 3 - Sep 4
Marrero's Guest Mansion

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

3.5 star property
9.8 out of 10, Exceptional, (110)
"Awesome place! Will stay again!"
The price is ¥18,423
¥24,930 total
includes taxes & fees
Sep 8 - Sep 9
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Douglas House

3.0 star property
9.6 out of 10, Exceptional, (159)
"Such a beautiful property. "
The price is ¥19,837
¥23,096 total
includes taxes & fees
Sep 28 - Sep 29
Douglas House

Ambrosia Key West

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Loved the Ambrosia and would definitely stay here again. Location is excellent, very walkable, we didnt need our car for the entire stay. Hotel is quiet and staff are very welcoming. "
The price is ¥22,407
¥25,208 total
includes taxes & fees
Sep 1 - Sep 2
Ambrosia Key West

H2O Suites - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (551)
"This was the best stay I had in a long time felt like I was in the safest place in America very friendly environment people are warm and welcoming I will definitely be back soon and the concierge Winfield was amazing during my stay I love the environment and place very relaxing "
The price is ¥38,143
¥49,538 total
includes taxes & fees
Sep 2 - Sep 3
H2O Suites - Adults Only

Tropical Inn

3.5 star property
9.4 out of 10, Exceptional, (344)
"Great spot "
The price is ¥26,762
¥33,790 total
includes taxes & fees
Sep 1 - Sep 2
Tropical Inn

Ella's Cottages - Key West Historic Inns

3.5 star property
9.4 out of 10, Exceptional, (367)
"Loved our stay. "
The price is ¥30,824
¥42,133 total
includes taxes & fees
Sep 8 - Sep 9
Ella's Cottages - Key West Historic Inns

Westwinds Inn

3.5 star property
9.4 out of 10, Exceptional, (1006)
"Great location and very cute place. We’ll definitely be back. "
Westwinds Inn

The Grand Guesthouse

2.5 star property
9.6 out of 10, Exceptional, (1003)
"Great place and a great value. Very clean & a comfortable bed."
The Grand Guesthouse
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.

Top Jackson Square Hotel Reviews

Hotels near Other Key West Attractions

Duval Street
Duval Street featuring signage

Duval Street

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.

Harry S. Truman Little White House
Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Ernest Hemingway Home and Museum
Ernest Hemingway Home and Museum featuring heritage elements and a house

Ernest Hemingway Home and Museum

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

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Explore a world of travel with Expedia

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 1762 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 Hyatt Centric Key West Resort and Spa and Southernmost Beach Resort and Guesthouses.

How many hotels will I be able to find close to Jackson Square?

Expedia has 1762 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 Saint Mary Star of the Sea 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.