Hotels near Jackson Square

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Dec 27 - Dec 28
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Dec 28 - Dec 29
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Jan 2 - Jan 4
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Jan 9 - Jan 11

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Our top choices for Jackson Square hotels

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, (1000)
"Great location, spotless rooms, attentive and friendly staff, great value."
United States
David
The price is P23,070
P25,954 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Almond Tree Inn Hotel - Adults Only
Balcony
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, (884)
"I loved staying here! The room was great and the staff was awesome! "
United States
Tiffany
The price is P17,565
P19,761 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Simonton Court Historic Inn & Cottages
Terrace/patio
The Gardens Hotel

The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1001)
"Loved it. The staff were very friendly and the place was classic Key West."
United States
Ben
The price is P23,759
P26,729 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Gardens Hotel
Exterior
The Marquesa Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1000)
"Perfect place to stay. "
United States
Paulette
The price is P23,440
P29,675 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Marquesa Hotel
Exterior
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, (1001)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is P22,820
P25,673 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Orchid Key Inn - Adults Only
Outdoor pool, sun loungers
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, (276)
"Great place"
United States
Carol A
The Mermaid & Alligator
View from room
H2O Suites - Adults Only

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, (582)
"Great place!!"
United States
Joel
The price is P29,315
P36,945 total
includes taxes & fees
Jan 4 - Jan 5, 2026
H2O Suites - Adults Only
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, (469)
"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 P18,478
P20,788 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Coco Plum Inn
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, (364)
"Nice place to stay "
United States
yulio
The price is P16,221
P19,718 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tropical Inn
Fountain
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, (1000)
"Excellent stay"
United States
Emily Barbara
The price is P23,560
P26,505 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Island City House Hotel
Garden
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, (236)
"Excellent spot, I definitely recommended"
United States
Paul
The price is P14,377
P17,791 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Douglas House
Exterior
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, (1000)
"Great stay"
United States
Ginger
The Grand Guesthouse
Courtyard
Santa Maria Suites

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, (1000)
"Awesome place we loved it"
United States
Josh
The price is P29,902
P37,605 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Santa Maria Suites
Outdoor pool, pool umbrellas, sun loungers
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)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is P22,030
P24,784 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Marrero's Guest Mansion
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, (997)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is P21,090
P23,726 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Weatherstation Inn
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, (1001)
"Great place to stay"
United States
Melody
The price is P16,928
P19,044 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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, (413)
"The cottage was perfect, centrally located and a wonderful place to stay!"
United States
Claudia
The price is P23,501
P29,418 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ella's Cottages - Key West Historic Inns
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, (1001)
"Enjoyed our stay."
United States
Cindy
Westwinds Inn
Outdoor pool
Silver Palms Inn

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, (1005)
"everything is great, love the room, the location, and the quiet ac"
United States
Qi
The price is P14,223
P19,966 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Silver Palms Inn
Terrace/patio
Southernmost House

Southernmost House

Southernmost House
4.0 star property
Uptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1000)
"Great place to stay. Staff was very friendly"
United States
Jacob
The price is P21,572
P29,721 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Southernmost House
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.
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Top Jackson Square Hotel Reviews

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Great location. Staff is very friendly."
Tianqi 2-night trip
Posted 3 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.
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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 1794 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 Heron House - Adult Only.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1794 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.
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 Red Barn Theater, Key West Film Society, and Waterfront Playhouse.