Hotels near Jackson Square

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Jackson Square hotels

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, (1002)
"Very nice & peaceful with a wonderful staff. Our second time staying here"
United States
Sandra
The price is S$570
includes taxes & fees
6 Jan - 7 Jan, 2026
Almond Tree Inn Hotel - Adults Only
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, (880)
"Really enjoyed my stay. The staff were super friendly, and the location was amazing—close to all the Old Town activities! "
United States
Leonid
The price is S$416
includes taxes & fees
21 Dec - 22 Dec
Simonton Court Historic Inn & Cottages
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, (1002)
"Perfect place to stay. "
United States
Paulette
The price is S$841
includes taxes & fees
21 Dec - 22 Dec
The Marquesa Hotel
Exterior detail
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, (1000)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
The price is S$652
includes taxes & fees
20 Dec - 21 Dec
The Gardens Hotel
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, (246)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
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, (1002)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is S$564
includes taxes & fees
6 Jan - 7 Jan, 2026
Orchid Key Inn - Adults Only
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, (131)
"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
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, (363)
"The place was excellent and the service amazing "
United States
Janae
The price is S$348
includes taxes & fees
21 Dec - 22 Dec
Tropical Inn
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, (581)
"Great place!!"
United States
Joel
The price is S$725
includes taxes & fees
21 Dec - 22 Dec
H2O Suites - Adults Only
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, (1000)
"Excellent stay"
United States
Emily Barbara
The price is S$552
includes taxes & fees
20 Dec - 21 Dec
Island City House Hotel
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, (922)
"A great no hassle stay."
United States
Gary
The price is S$369
includes taxes & fees
8 Jan - 9 Jan, 2026
L'Habitation Guest 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)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is S$472
includes taxes & fees
4 Jan - 5 Jan, 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, (995)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is S$391
includes taxes & fees
21 Dec - 22 Dec
Weatherstation Inn
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, (1004)
"Great location and loved the heated pool!"
United States
Tammy
Westwinds Inn
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, (1000)
"Great stay"
United States
Ginger
The price is S$382
includes taxes & fees
20 Dec - 21 Dec
The Grand Guesthouse
2 outdoor pools, pool loungers
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, (1003)
"Awesome place we loved it"
United States
Josh
The price is S$833
includes taxes & fees
13 Jan - 14 Jan, 2026
Santa Maria Suites
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, (1024)
"We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast."
United States
Susanne
The price is S$419
includes taxes & fees
6 Jan - 7 Jan, 2026
Silver Palms Inn
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, (408)
"The cottage was perfect, centrally located and a wonderful place to stay!"
United States
Claudia
The price is S$644
includes taxes & fees
22 Dec - 23 Dec
Ella's Cottages - Key West Historic Inns
Front of property
Caribbean House

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (285)
"Very nice and would stay again. It was close to a few of our favorite restaurants "
United States
Leonard Frisch
The price is S$354
includes taxes & fees
21 Dec - 22 Dec
Caribbean House
Property grounds
Paradise Inn Key West - Adults Only

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, (1005)
"Cozy place right near everything "
United States
Joseph
Paradise Inn Key West - Adults Only
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Bar staff is awesome!"
Tracey 7-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses

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.
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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 1801 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 The Cabana Inn Key West - Adults Only and Heron House - Adult Only.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1801 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 Key West Film Society, Red Barn Theater and Waterfront Playhouse.