The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

Find hotels near Jackson Square, Key West from ₩171,114

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Check prices for these dates

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 0.6 km from Jackson Square
United States
John
₩238,872
₩268,731 total
includes taxes & fees
Sep 30 - Oct 1
Almond Tree Inn Hotel - Adults Only

2. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
Nicholas
₩238,872
₩268,731 total
includes taxes & fees
Sep 30 - Oct 1
Orchid Key Inn - Adults Only

3. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Forrest
₩307,806
₩346,282 total
includes taxes & fees
Sep 30 - Oct 1
The Gardens Hotel

4. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
₩309,889
₩424,859 total
includes taxes & fees
Sep 24 - Sep 25
The Marquesa Hotel

5. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
John
₩224,438
₩252,493 total
includes taxes & fees
Sep 29 - Sep 30
The Conch House Heritage Inn

6. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.1 km from Jackson Square
United States
Nestor
₩120,961
₩186,910 total
includes taxes & fees
Sep 24 - Sep 25
Alexander's Guesthouse - Adult Exclusive

7. Key West Villas

Key West Villas
Downtown Key West, 0.3 km from Jackson Square
United States
Margaret
₩352,514
₩396,588 total
includes taxes & fees
Oct 15 - Oct 16
Key West Villas

8. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Kourosh
₩378,129
₩516,878 total
includes taxes & fees
Sep 27 - Sep 28
H2O Suites - Adults Only

9. Tropical Inn

Tropical Inn
Downtown Key West, 0.4 km from Jackson Square
United States
Molly
₩130,746
₩180,974 total
includes taxes & fees
Sep 27 - Sep 28
Tropical Inn

10. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Osvaldo
₩208,378
₩234,424 total
includes taxes & fees
Sep 24 - Sep 25
Island City House Hotel

11. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Alissa
₩152,898
₩205,894 total
includes taxes & fees
Sep 24 - Sep 25
The Grand Guesthouse

12. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United States
michael
₩138,274
₩171,114 total
includes taxes & fees
Sep 24 - Sep 25
Douglas House - Adults Only

13. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Brian
₩243,954
₩274,449 total
includes taxes & fees
Sep 28 - Sep 29
The Mermaid & Alligator

14. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Anthony
₩378,129
₩516,878 total
includes taxes & fees
Sep 27 - Sep 28
Santa Maria Suites

15. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Anne
₩148,365
₩196,447 total
includes taxes & fees
Oct 5 - Oct 6
Duval House

16. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Tricia
₩157,554
₩177,249 total
includes taxes & fees
Sep 27 - Sep 28
Westwinds Inn

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
sam
₩108,560
₩213,623 total
includes taxes & fees
Sep 28 - Sep 29
Silver Palms Inn & Historic Homes

18. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.2 km from Jackson Square
United States
Andrew
₩163,820
₩184,303 total
includes taxes & fees
Sep 24 - Sep 25
Alexander Palms Court

19. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.3 km from Jackson Square
United States
Svetlana
₩229,046
₩257,677 total
includes taxes & fees
Sep 24 - Sep 25
Weatherstation Inn

20. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
Tricia
₩184,426
₩207,479 total
includes taxes & fees
Sep 27 - Sep 28
Ambrosia Key West
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Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,006 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,002 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,002 reviews
View
A two-story house with a covered porch, a brick pathway, and a large tree.
The Marquesa Hotel
9.8
Exceptional
1,001 reviews
View
A porch with a white railing, a bench, and a flag.
The Conch House Heritage Inn
9.8
Exceptional
189 reviews
View

Top Jackson Square Hotel Reviews

Douglas House - Adults Only

Douglas House - Adults Only

10/10 Excellent
"We stay at The Douglas House often and it’s always perfect! This time was no exception - great staff, clean rooms and well kept property. Location is perfect for easily getting anywhere on the island! We will definitely be back, hopefully soon!"
Kathleen 5-night trip
Posted 1 hour ago
Douglas House - Adults Only
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"The facility was beautiful and the amenities were great! just keep in mind it is a walk to the seaport and the main part of Duval, which became a little too far to walk back in forth, which we knew it would be a walk when we booked it."
Darlene 2-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"The resort was well maintained, the staff very friendly, the beach, pool and restaurant made for an amazing vacation."
Cheryl 5-night trip
Posted 4 hours ago
Pier House Resort & Spa
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Beautiful place, very nice pool, nice spacious rooms. Wonderful staff."
Valerie 4-night trip
Posted 7 hours ago
The Gardens Hotel
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"This property was the perfect spot for seeing all of Key West. We had a brief problem with our door and the team was so responsive and apologetic and offered things to make it right. Have already recommended to friends and family in the 24hrs of being home."
Tammi 3-night trip
Posted 18 hours ago
Winslow's Bungalows - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

8/10 Good
"It was all about location for me"
Levi 3-night trip
Posted 19 hours ago
Heron House - Adult Only
Duval House

Duval House

10/10 Excellent
"Loved the chilled pool!"
Alicia 4-night trip
Posted 2 days ago
Duval House
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Great stay. Clean and well Maintained. Friendly staff."
ALEASE 3-night trip
Posted 2 days ago
The Cabana Inn Key West - Adults Only
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Always love staying at the Opal."
SHANNON 6-night trip
Posted 2 days ago
Opal Key Resort & Marina, Key West

Other attractions near Jackson Square

A historic building with ornate architecture, a balcony, and a coat of arms.

San Carlos Institute - Casa Cuba

8.6/10 (34 reviews)
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 beautiful beaches or experience its lively festivals.
See properties
A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 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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We Cycle Key West

You can search for that perfect souvenir at We Cycle Key West during your trip to Key West.
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St. Paul's Episcopal Church

9.0/10 (73 reviews)
St. Paul's Episcopal Church is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its lively festivals.
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Key West Film Society

7.6/10 (9 reviews)
You can get tickets for a performance at Key West Film Society during your stay in Key West. In the area, take in the lively festivals and beautiful sunsets.
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The Key West Theater

You can make plans for a show at The Key West Theater on your trip to Key West. Discover the area's great live music, or seek out its biking trails.
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Red Barn Theater

8.0/10 (10 reviews)
You can enjoy a show at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.
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Hellings House Museum

You can spend an afternoon exploring the galleries in Hellings House Museum during your trip to Key West. Experience the area's entertainment choices and great live music.
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 1672 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 Southernmost Beach Resort and Guesthouses and Pier House Resort & Spa.
How many hotels will I be able to find close to Jackson Square?
Expedia has 1672 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, Mel Fisher Maritime Museum, 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 Fort East Martello Museum and Gallery 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.