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26 Dec - 27 Dec
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27 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Jackson Square hotels

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top 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, (1004)
"Great location, spotless rooms, attentive and friendly staff, great value."
United States
David
The price is ฿12,202
฿13,728 total
includes taxes & fees
6 Jan - 7 Jan 2026
Almond Tree Inn Hotel - Adults Only
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, (247)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
King Room D | 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 ฿13,330
฿14,997 total
includes taxes & fees
6 Jan - 7 Jan 2026
Simonton Court Historic Inn & Cottages
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 ฿10,302
฿11,590 total
includes taxes & fees
6 Jan - 7 Jan 2026
Coco Plum Inn
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, (1003)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is ฿12,070
฿13,579 total
includes taxes & fees
6 Jan - 7 Jan 2026
Orchid Key Inn - Adults Only
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 ฿12,398
฿15,696 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Marquesa Hotel
Outdoor pool, pool 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
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 ฿12,445
฿14,000 total
includes taxes & fees
13 Jan - 14 Jan 2026
Island City House Hotel
11 Gecko's Garden - Adults Only | Premium bedding, pillow-top 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 ฿10,415
฿12,494 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tropical Inn
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, (925)
"A great no hassle stay."
United States
Gary
The price is ฿7,888
฿8,874 total
includes taxes & fees
8 Jan - 9 Jan 2026
L'Habitation Guest House
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 ฿6,366
฿7,878 total
includes taxes & fees
7 Jan - 8 Jan 2026
Douglas House
Deluxe Suite, 1 King Bed, Private Pool | 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 ฿15,505
฿19,541 total
includes taxes & fees
6 Jan - 7 Jan 2026
H2O Suites - Adults Only
3 outdoor pools, a heated pool, pool 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 ฿8,954
฿10,073 total
includes taxes & fees
6 Jan - 7 Jan 2026
Ambrosia Key West
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 ฿11,157
฿12,551 total
includes taxes & fees
26 Jan - 27 Jan 2026
Weatherstation Inn
Outdoor pool, pool umbrellas, pool 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 ฿11,652
฿13,109 total
includes taxes & fees
13 Jan - 14 Jan 2026
Marrero's Guest Mansion
View from property
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, (1004)
"I loved this place the location was absolutely perfect "
United States
Frank
The price is ฿7,737
฿9,372 total
includes taxes & fees
6 Jan - 7 Jan 2026
Duval 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
Outdoor pool, open 8:00 AM to 10:00 PM, pool 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 ฿12,415
฿15,541 total
includes taxes & fees
5 Jan - 6 Jan 2026
Ella's Cottages - Key West Historic Inns
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, (1011)
"Very friendly staff, directly in City Center. "
Germany
Philip
The price is ฿7,103
฿10,089 total
includes taxes & fees
6 Jan - 7 Jan 2026
Silver Palms Inn
Terrace/patio
Caribbean House

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (290)
"Very nice and would stay again. It was close to a few of our favorite restaurants "
United States
Leonard Frisch
The price is ฿10,276
฿12,338 total
includes taxes & fees
6 Jan - 7 Jan 2026
Caribbean 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

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"All accommodations were outstanding!"
Bob 4-night trip
Posted 2 days ago
Pier House Resort & Spa

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 cycling. If you're looking for a convenient place to stay, take a look at the 1795 hotels and other accommodation options you'll find within a mile.
What's the best hotel 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 traveller data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include Hyatt Centric Key West Resort and Spa and The Cabana Inn Key West - Adults Only.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1795 hotels and other accommodation options 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, you'll find most hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to get the top deals on offer 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.