Find hotels near Jackson Square, Key West from ￥40,519

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jan 11 - Jan 12
Tomorrow
Jan 12 - Jan 13
Next weekend
Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Jackson Square hotels

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only

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, (1,001 reviews)
"Clean room , friendly staff , excellent location . Would stay again ! "
United States
Kathleen
The price is ￥70,293
￥79,080 total
includes taxes & fees
Jan 13 - Jan 14
Almond Tree Inn Hotel - Adults Only
Exterior
The Marquesa Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,001 reviews)
"Perfect place to stay. "
United States
Paulette
The price is ￥55,277
￥71,069 total
includes taxes & fees
Jan 12 - Jan 13
The Marquesa Hotel
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (896 reviews)
"I loved staying here! The room was great and the staff was awesome! "
United States
Tiffany
The price is ￥46,265
￥52,049 total
includes taxes & fees
Jan 12 - Jan 13
Simonton Court Historic Inn & Cottages
Front of property
Key West Villas

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (248 reviews)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
Exterior
Coco Plum Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.6 out of 10, Exceptional, (476 reviews)
"The Coco Plum Inn is a wonderful place to stay. Staff is fantastic and the location is perfect. We will definitely come back and stay at the Coco Plum Inn."
United States
Brent
The price is ￥46,751
￥52,596 total
includes taxes & fees
Jan 12 - Jan 13
Coco Plum Inn
Property grounds
Orchid Key Inn - 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)
"Convenient location, staff was friendly and helpful"
United States
Melissa
The price is ￥58,688
￥66,023 total
includes taxes & fees
Jan 13 - Jan 14
Orchid Key Inn - Adults Only
Audubon Room - Adult Exclusive | Terrace/patio
The Mermaid & Alligator

The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 0.8 km from Jackson Square
9.8 out of 10, Exceptional, (278 reviews)
"It is very quaint, clean, has a friendly atmosphere & has a great location. We love going there!"
United States
Bradley
The Mermaid & Alligator
Front of property
L'Habitation Guest House

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.2 km from Jackson Square
9.4 out of 10, Exceptional, (930 reviews)
"Great location "
United States
Scott
The price is ￥51,946
￥58,440 total
includes taxes & fees
Jan 20 - Jan 21
L'Habitation Guest House
11 Gecko's Garden - Adults Only | Premium bedding, pillowtop beds, individually decorated
Tropical Inn

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (367 reviews)
"Nice place to stay "
United States
yulio
The price is ￥57,942
￥69,131 total
includes taxes & fees
Jan 13 - Jan 14
Tropical Inn
Cigar House King Suite w/ Poolside porch | Balcony view
Island City House Hotel

Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.6 km from Jackson Square
9.6 out of 10, Exceptional, (1,000 reviews)
"Excellent stay"
United States
Emily Barbara
The price is ￥57,749
￥64,967 total
includes taxes & fees
Jan 12 - Jan 13
Island City House Hotel
Exterior
Douglas House

Douglas House

Douglas House
3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (248 reviews)
"Loved the hotel will definitely stay again "
United States
Christina
The price is ￥41,084
￥50,839 total
includes taxes & fees
Jan 14 - Jan 15
Douglas House
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,001 reviews)
"The staff was outstanding and this location was very convenient, yet located away from the hustle and bustle of the main area."
United States
William
The price is ￥48,788
￥54,887 total
includes taxes & fees
Jan 12 - Jan 13
Weatherstation Inn
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | Free WiFi, bed sheets
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West, 1.1 km from Jackson Square
9.8 out of 10, Exceptional, (138 reviews)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Property grounds
Duval House

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,018 reviews)
"Great place! "
United States
David
The price is ￥32,999
￥40,519 total
includes taxes & fees
Jan 14 - Jan 15
Duval House
Terrace/patio
Marrero's Guest Mansion

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, (335 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is ￥59,209
￥66,611 total
includes taxes & fees
Jan 13 - Jan 14
Marrero's Guest Mansion
3 outdoor pools, a heated pool, sun loungers
Ambrosia Key West

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, (1,000 reviews)
"Great place to stay"
United States
Melody
The price is ￥38,785
￥43,633 total
includes taxes & fees
Jan 12 - Jan 13
Ambrosia Key West
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (421 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is ￥70,861
￥87,712 total
includes taxes & fees
Jan 12 - Jan 13
Ella's Cottages - Key West Historic Inns
Courtyard
The Grand Guesthouse

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, (1,003 reviews)
"Great stay"
United States
Ginger
The Grand Guesthouse
Lobby sitting area
Westwinds Inn

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,005 reviews)
"Enjoyed our stay."
United States
Cindy
Westwinds Inn
Exterior
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Historic Seaport, 0.2 km from Jackson Square
9.0 out of 10, Wonderful, (311 reviews)
"Clean, super comfortable, close to everything"
United States
Virginia
The price is ￥49,577
￥61,103 total
includes taxes & fees
Jan 25 - Jan 26
La Concha Key West, Autograph Collection
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.
View all properties

Top Jackson Square Hotel Reviews

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Leave me alone"
George 1-night trip
Posted 4 days ago
Opal Key Resort & Marina, Key West

Hotels near other Jackson Square attractions

KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"

San Carlos Institute - Casa Cuba

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 seaside or experience its lively festivals.
See properties
Vibrant atmosphere at Duval Street showcases Key West's historic charm and cultural richness in Florida's lively district

Duval Street

4.5/5 (9,716 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.
See properties

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 1797 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 The Cabana Inn Key West - Adults Only and Hyatt Centric Key West Resort and Spa.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1797 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 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, Key West Historic Seaport, and Fort Zachary Taylor Historic State Park 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.