Hotels near Jackson Square

  • 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
16 Jan - 17 Jan
Tomorrow
17 Jan - 18 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Filter by

Guest rating
Guest rating
Star rating

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
3.5 star property
Downtown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1,000 reviews)
"Clean room , friendly staff , excellent location . Would stay again ! "
United States
Kathleen
The price is RM1,834
RM2,063 total
includes taxes & fees
19 Jan - 20 Jan
Almond Tree Inn Hotel - Adults Only
Exterior

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, (1,000 reviews)
"Perfect place to stay. "
United States
Paulette
The price is RM1,675
RM2,113 total
includes taxes & fees
19 Jan - 20 Jan
The Marquesa Hotel
Exterior detail

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, (1,000 reviews)
"Good place"
United States
Salvador
The price is RM1,820
RM2,048 total
includes taxes & fees
18 Jan - 19 Jan
The Gardens Hotel
Property grounds

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, (1,004 reviews)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is RM1,834
RM2,063 total
includes taxes & fees
19 Jan - 20 Jan
Orchid Key Inn - Adults Only
Balcony view

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, (999 reviews)
"Excellent stay"
United States
Emily Barbara
The price is RM1,410
RM1,586 total
includes taxes & fees
19 Jan - 20 Jan
Island City House Hotel
View from room

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 reviews)
"Great place!!"
United States
Joel
The price is RM2,875
RM3,508 total
includes taxes & fees
25 Jan - 26 Jan
H2O Suites - Adults Only
3 outdoor pools, a heated pool, pool loungers

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 RM1,168
RM1,315 total
includes taxes & fees
20 Jan - 21 Jan
Ambrosia Key West
Courtyard

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, (1,001 reviews)
"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
3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (425 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is RM2,065
RM2,528 total
includes taxes & fees
26 Jan - 27 Jan
Ella's Cottages - Key West Historic Inns
2 outdoor pools, pool loungers

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, (1,000 reviews)
"Awesome place we loved it"
United States
Josh
The price is RM1,861
RM2,368 total
includes taxes & fees
21 Jan - 22 Jan
Santa Maria Suites
Front of property – evening/night

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,012 reviews)
"The staff was so friendly and the amenities were perfect. Great location to watch the sunset at. "
United States
Jamie
The price is RM2,084
RM2,504 total
includes taxes & fees
25 Jan - 26 Jan
Opal Key Resort & Marina, Key West
Porch

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.0 out of 10, Wonderful, (1,140 reviews)
"Great location to Duval street and restaurants "
United States
Kelly
The price is RM1,410
RM1,747 total
includes taxes & fees
3 Feb - 4 Feb
Heron House - Adult Only
Outdoor pool, pool loungers

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1,003 reviews)
"Upon arrival everything about this resort, the staff the room the views made our trip to Key West that much better thank you"
United States
Randy
The price is RM2,267
RM2,865 total
includes taxes & fees
20 Jan - 21 Jan
Ocean Key Resort - A Noble House Resort
Exterior

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (867 reviews)
"What a amazing place to stay from the service to the rooms spectacular "
United States
John
The price is RM1,820
RM2,253 total
includes taxes & fees
19 Jan - 20 Jan
Ridley House - Key West Historic Inns
Front of property – evening/night

Southernmost House

Southernmost House
4.0 star property
Uptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1,000 reviews)
"Good staff, clean room, nice breakfast, good location"
United States
Noelle
The price is RM2,592
RM3,292 total
includes taxes & fees
4 Feb - 5 Feb
Southernmost House
Outdoor pool

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.2 out of 10, Wonderful, (1,005 reviews)
"Clean room, nice bed, nice staff, great location."
United States
Valerie
The price is RM982
RM1,378 total
includes taxes & fees
19 Jan - 20 Jan
Silver Palms Inn
Outdoor spa tub

Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
3.0 star property
Downtown Key West, 0.5 km from Jackson Square
9.0 out of 10, Wonderful, (409 reviews)
"The room we had was absolutely great and perfect for us"
United States
robin
The price is RM1,073
RM1,412 total
includes taxes & fees
20 Jan - 21 Jan
Seascape Tropical Inn - Adult Exclusive
Front of property

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West, 0.8 km from Jackson Square
9.2 out of 10, Wonderful, (1,118 reviews)
"Great place , amazing breakfast, staff was very nice "
United States
Robert
The price is RM1,830
RM2,264 total
includes taxes & fees
20 Jan - 21 Jan
Winslow's Bungalows - Key West Historic Inns
Food and drink

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only
3.0 star property
Downtown Key West, < 0.1 km from Jackson Square
8.8 out of 10, Excellent, (1,000 reviews)
"Staff friendly very accommodating very clean room"
United States
Terry
The Cabana Inn Key West - Adults Only
Room amenity

Alexander Palms Court

Alexander Palms Court
2.5 star property
Casa Marina, 1.2 km from Jackson Square
9.2 out of 10, Wonderful, (1,000 reviews)
"Excellent stay, beautiful property"
United States
Ivan
The price is RM1,566
RM1,761 total
includes taxes & fees
18 Jan - 19 Jan
Alexander Palms Court
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

Duval House

Duval House

10/10 Excellent
"Duval House was the quaintest, cute, cozy, comfortable place I’ve ever stayed in KW. We are from Key Largo and travel down every couple months. This will be our new spot! Perfect spot, on Duval, awesome room, cute, HEATED pool amazing! The breakfast was delicious, every staff member was personable and kind!!10 out of 10 for sure! Can’t wait to go back! "
Kelly 1-night trip
Posted 5 days ago
Duval House

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 cycling. If you're looking for a convenient place to stay, take a look at the 1798 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 Southernmost Beach Resort and Guesthouses and The Cabana Inn Key West - Adults Only.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1798 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, Fort Zachary Taylor Historic State Park and Curry Mansion Museum 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.